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Thursday, midday. Paul Noth is in Milwaukee, where he moved back after 20 years split between the Upper East Side and the Princeton area, and where he now has, as he put it while wandering to another room mid-stream to chase better WiFi, multiple rooms. (We get it, Paul. You don’t live in Manhattan anymore.)

First order of business: it’s Noth, rhymes with both. He’s been letting people say “Nawth” for decades out of Midwestern politeness. Gosh. Consider yourselves corrected on his behalf. If you missed it live, the replay is above. Here’s what happened, with every link we promised on air down the bottom…

Pre-orderers get a signed bookplate posted to them! Just shoot him an email at paul@paulnoth.com with your mailing address and your desired inscription. (A proof-of-purchase screenshot is also much appreciated.)

You know Paul’s most famous cartoon even if you don’t know his name: the flock of sheep gazing up at a billboard of a wolf, captioned “He tells it like it is.” It’s among the most shared cartoons in the magazine’s history; it’s now the cover of his book, and Paul has mixed feelings about its immortality. “It should be a historical document by now,. he said, a little wearily.

Here’s the detail that should be laminated and handed to every rejected cartoonist on earth: The New Yorker rejected it the first time he submitted it. So did they reject his other most popular cartoons, first time ‘round. Paul resubmits. He always has, fortified by a story he’d heard about Saul Steinberg, who supposedly used to take his rejected cartoons, put them straight into a fresh envelope, and post them back to the magazine. (The balls on this guy! I love him.)

Paul sold to The New Yorker in 2004. The cartoon: a White House press secretary holding a torch under his chin like a kid telling a ghost story, while a reporter asks how he responds to critics who say he’s just trying to scare people. He’d worked on that batch for the best part of 2 months under the wing of Matt Diffee, whom he’d met at the Rejection Show and who walked the batch in to Bob Mankoff.

At Paul’s first look meeting, surrounded by his heroes (Gahan Wilson among them), Mankoff greeted the new arrival with two sentences that became his entire art education. The first: “Don’t get cocky.” The second: “I want to see 10 a week from you, even if they’re s**t.”

Paul has done 10 a week ever since, through every all-nighter, every TV job, every book. “It was my art school in a lot of ways,” he said. Like me, he’d never been to one. He’d never had art in public before. He learned to draw in public, 10 at a time, and eventually stripped away his early etching-style hatch marks when he realised the truth every gag cartoonist arrives at eventually: “The best style for me was the best execution of the joke.” Or as Lee Lorenz put it in The Art of the New Yorker, which we both worship: a cartoon is beautiful the way a sailboat is beautiful. It has exactly what it needs to function, and nothing else.

Mankoff gave me my version of that lecture too, around 2014, back when I wore a suit jacket to the offices like I was auditioning for a bank. He looked at my batch of borrowed styles and asked what I think about when I do my hair in the morning. “Try and think about your drawings as your hairdo. It’s a style you’ve arrived at. You’re not trying to copy Johnny Depp.” This from a man with famously luxurious amounts of hair. It worked, though. It worked on both of us.

The Pale Force story is even better than I’d hoped. Jim Gaffigan, it turns out, is Paul’s brother-in-law; he’d married Paul’s sister a year or two before. Paul, not yet a New Yorker cartoonist, pitched Jim an animated bit for Late Night with Conan O’Brien, modelled on Steve Martin turning up to Letterman with something weird in his back pocket. When the head writer asked whether he’d done animation before, Paul said yes. (He had made flip books, so… technically not a lie?)

The budget was roughly what a guest gets paid for sitting on the couch, which is not a number that produces animation, and his first delivery came back with the note that a 16-megabyte video file cannot be broadcast on network television. The night the first episode aired, running on no sleep, he watched it freeze for a single millisecond and briefly died. Then it killed, the series got Emmy-nominated, and Paul got a comedy education by osmosis: Robert Smigel, Brian Stack and Demetri Martin down the hall, Conan’s face providing the biggest laugh of every episode no matter what Paul animated. His conclusion, having vowed never to do low-budget animation again:

Worth it.

The Laureate Report…

I put the important questions to Wisconsin’s inaugural Cartoonist Laureate, and I can now report the following to the people. There is no salary. There is no diplomatic immunity. There is, crucially, no sash: “I have to make the sash myself, apparently. Like a Mayor McCheese-style sash.” His opening list of demands included full access to the Oscar Mayer Wienermobile. His actual duties, in his own words: “to figure out what the hell the cartoonist laureate does.” So far that means cartoon classes for kids, library outreach, trying to attach a cash prize for whoever comes next (”that’s what cartoonists actually need let’s be real”), and a retrospective of 175 of his originals opening at the Museum of Wisconsin Art in January, sharing a title with the book. When the museum’s president first floated the laureateship, Paul assumed she meant Lynda Barry, P.S. Mueller or Craig Thompson. She meant him.

His process, for the process junkies: 10 ideas written first thing every morning, “usually bad”, purely to switch on the part of the brain that notices things. Voice memos through the day, transcribed the next morning. And this, which made my week: Paul had listened to Tuesday’s episode with Brian Biggs and co-signed the boredom sermon. “If I keep the stimulus away, I just keep things mentally kind of quiet; I will start entertaining myself after a while.” Three episodes ago this was my crank theory. It is now, I’m declaring, the official position of the show.

Somewhere in here Matt Diffee himself materialised in the chat, speak of the devil, and was informed we’d been blaming everything wrong in Paul’s life on him. For the record: Diffee ushered in a whole generation of cartoonists, Paul among them, and his Rejection Collection books are the sacred texts of everything above.

Paul’s dad was a lifelong newspaper man who brought home cartoon collections from the feature desk for his cartoon-obsessed kid, and who gave him one piece of career advice: don’t go into print media. He could see the writing on the wall. So Paul didn’t pursue it. He tried screenplays, plays, other lives. “I look back at an old notebook where I was trying to write a screenplay,” he said, “and the margins are just full of cartoons. In retrospect, it should have been obvious.”

At the end, Paul described what this show apparently is: “It’s basically like a digital cartoonist lunch.” The magazine’s cartoonists used to eat together every Tuesday. We don’t anymore. I suppose I’ve been rebuilding the table an hour at a time, and I couldn’t be happier about who keeps sitting down at it.

Now, the promised links…

Pre-order I Am Going to Eat You... and Other Awkward Truths

Out 13 October, 200+ of his most-loved cartoons plus 50 never published, and Paul says the unpublished ones “are usually the funniest ones, to be honest”.

Pre-orderers get a signed bookplate posted to them! Just shoot him an email at paul@paulnoth.com with your mailing address and your desired inscription. (A proof-of-purchase screenshot is also much appreciated.)

Pre-orders are everything in publishing now, so if you were going to buy it anyway, buying it today is the whole ballgame. And since our books share a birthday: pre-order You’re Not a Real Parent Until... (👉 Pre-order here )

Oh! —and I’ll draw your kids, or grandkids, into the book!

‘til next time!Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

Wednesday, midday… Brian Biggs is alone in his Philadelphia studio, an old garage he describes as a hermit cave, holding his phone in one hand and a pen in the other. I’m at my drawing board doing the same. For the next hour, 90 people watched 2 grown men show each other their doodles.

If you missed it live, the replay is above. What follows is what you missed, with links to everything we held up to the camera.

Brian has made more than 80 books. The Everything Goes series, Tinyville Town, the New York Times-bestselling Frank Einstein books with Jon Scieszka. So naturally, when he started his Substack, the imposter syndrome turned up anyway. “I had to give myself a break,” he said, “and get past my oh-no ego and just let it happen.”

“All I want to do, man, is just draw. I just want to draw. When I was a kid, I got in trouble for drawing and telling stories… and I have to remember that I’m 58 and that’s what I do every day now.

The turn came on an exercise bike in his basement, listening to Giuseppe Castellano’s podcast episode with myself and Adam Ming, where Adam Ming said to stop treating Substack as the road to being published and start treating it as being published. “It just was one of those ding moments,” Brian said. He got off the bike and got to work.

The work is The Walk, and the story behind it is every author’s recurring nightmare. In 2019, Brian published a picture book with Penguin called The Space Walk: an astronaut, alone in space, who just wants to go outside. It came out, in his words, “to the great yawn of indifference of children’s publishing”, and was out of print within a couple of years.

But out of print means the rights come home. So Brian is now turning that orphaned story into a full graphic novel, and serialising every step of it on his Substack: thumbnails, wrong turns, existential wobbles, all of it. “Every stupid thought I’m having about this is going onto my Substack,” he said. The story is already mutinying. “The story has decided it wants to be something bigger than I think I want it to be,” he told me, having informed his wife that morning it might be three 200-page volumes. “I’m 58 years old, man. Do I have a 600-page graphic novel in front of me?”

The logic, though, is sound: last time, the book arrived to silence. This time, “at least it’s going to be a thing that there’s an audience built in already following it. And they care about it.” Every page will be hand-lettered, incidentally, because Brian letters the way you’d read it aloud, and he’d rather do that than make a font. He’s seen his hand-lettering redrawn by translators into Hebrew and Chinese, stroke by stroke. “I would love to meet those people one day,” he said, “but I’m afraid they would punch me in the face.”

Somewhere in the middle of all this I made him explain the line in his bio about being calligrapher to a princess, and I’m pleased to report it’s all true.

Junior year at Parsons, 1988, studying in Paris, he answered a job-board ad to address envelopes for a man in a cravat who threw parties for people like the Rothschilds. Which is how a kid from Texas, whose calligraphy career began with a drugstore Speedball set and the Renaissance Fairs of early-80s Houston, ended up hand-lettering the guest book for Princess Ghislaine de Polignac, whose family had been friends with Marie Antoinette, and who hosted Ronald and Nancy Reagan a few weeks later. Brian was escorted out as the Reagans arrived. He did the work at his apartment drawing table, Enya on the stereo (not sure which album…), his roommate’s Akira comics all over the futon.

A year or 2 later, he was waiting tables at a Bennigan’s, telling anyone who’d listen: “I was a calligrapher for a princess for a month.”

S**t Brushes and Other Filing Systems

Then I flipped the camera, and we got into the pens, as is my tradition. Highlights of the show-and-tell: his Kuretake brush pens, my Hunt 101, the ink bottle I suction-cup to train tables, and his filing system of labelled coffee cans reading “new brushes”, “good brushes” and (after asking the stream’s permission to swear) “s**t brushes”. He keeps a box labelled “used but might be useful on a rainy day”. He made it in 1994. It’s bloody full.

On Wednesday at 8pm, I did something I have never done in 20 years of cartooning: I drew a stork, live, on the internet, while two grown men discussed laundry detergent… (I know. Weird that it took me so long, right?!)

Let me back up.

I went live on Substack with my co-authors on a book we’re writing about how couples can run a home without slowly startin…

Carly Valancy beamed in from Valencia, Spain.

Some of you will remember Carly. She interviewed me on her Substack, A Good Omen, a while back. This week I got to return fire.

Four years ago, Carly reached out to the writer Alex Dobrenko`. When she interviewed him, she asked who she should talk to next. He said me. She sent me one email. I said yes. Then I sent her one email (”I know how busy you are, but...”), and she said yes. Somewhere since then, I also filled out the intake form for her next Reach Out Party cohort, which means I am now both her interviewer and her student, a conflict of interest I intend to exploit fully.

She told me my ask landed as a gift, not an imposition: “I ran outside and told my husband. You know what’s so cool? The chain of events that can happen from one email or DM.” That’s her entire body of work in a sentence. One email. Everything else is scaffolding.

Carly is a former actor. Broadway community, Hell’s Kitchen, 44th Street, the whole catastrophe. At about 25, stuck in a coffee shop job she hated and hunting for an agent, she did the thing that would become her life’s work without knowing it: she reached out to 1 stranger a day for 100 days.

It worked, in the boring, verifiable way these things sometimes do. She found an agent she’s still friends with. She booked a national tour. And around day 82, she finally mentioned the whole scheme to her acting coach, who was appalled. Not by the project. By the secrecy. “You have to tell people you’re doing this!” Then: “When you get to day 100, you should throw a party at the studio. I’ll host it. You can call it Carly Valancy’s Reach Out Party.”

She ran the 100 days again at 30, and the second lap taught her the lesson hiding inside the first:

“There was so much more beauty in the process, in who I became in it and how I found my voice. A lot of people treat networking as a means to an end. It’s something you do when you need something. Instead, think about it as a process of becoming.”

Carly has a phrase I’ve been carrying around like a lucky coin: increasing your surface area for luck. More reach-outs, more rooms, more chances for the universe to trip over you. Lately she’s refined it into something even better: “placing yourself in the current of serendipity”…

I asked her to define a good omen, given she’s named an entire publication after one. She gave me a visual instead:

“I’m going to give you a lava lamp. It’s constantly moving, and there’s some kind of glow about it where you’re just like, what is that thing? It’s got texture, and it’s alive.”

Then she gave me a better one, borrowed from the theatre director Anne Bogart, whom she cold-emailed (of course she did) with the same question:

Subscribe, rate, and please leave us a funny ⭐️⭐️⭐️⭐️⭐️ review wherever you listen to podcasts.

Welcome back for another episode of Is There Something In This?

Outside, seaplanes kept coming down the East River like they’d been thrown, and every twenty minutes Scott and I stopped mid-sentence to watch one not crash. One aborted, came around, and hit the water hard enough that we both made the noise. Nobody plans these segments.

I’m back from Columbus, where actual listeners turned up and forced us to describe our audience out loud. Here’s what we landed on: you’re pretentious, but you’re dumb enough to know you shouldn’t be. You want Barry Blitt on trade deficits, but you also want to know if the mouse has a really big dick. You are, in other words, exactly like us. (btw here’s a thing: I’m now live-drawing the ideas as we go, so the video version on Substack and YouTube is where you can watch me ruin a perfectly good joke in real time.)

Then we did the jokes. A jester’s head in the guillotine bucket, and the salesman who pitched the guillotine to the king as a workflow disruption. A MoMA guard with a new sign about muttering AI slop near the Van Gogh. A snowman in couples counselling, his wife a bucket of water: “I just think this summer has changed her.” A moth has an idea, and every moth for miles descends on it…

Somewhere in there, we stopped writing jokes and got onto the Flock cameras, the licence-plate network that lets cops look up their exes without a subpoena.

Also: the balls on the Big Merino, a pigeon with a hustle, a Borg water tower in Greenpoint, and a Gallagher courtroom gag from which Scott has formally removed his name. Because why not?

Our new book, You’re Not a Real Parent Until..., is out on October 13th and available for pre-order now wherever you buy books. It has, I’m reliably informed, already reached one bookshelf in Moscow.

By the way, if you want to binge all of our previous episodes in an endless playlist like it’s some kind of Netflix Drama that just got nominated for an Emmy®, you can find our entire backlog right here.

Send us your cartoon idea suggestions! We can’t guarantee we will read every one on the show, but we will read all messages we get here.

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▶ Be sure to send in your suggestions via Instagram @newyorkcartoons or yourenotarealemail@gmail.com. Cheers!

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▶ Check out our Facebook page at: www.facebook.com/ITSITpodcast

‘til next time!Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

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About twelve years ago, a teacher hired me to draw a caricature of her colleague as a gift. The colleague, she mentioned, was a New Yorker cartoonist. I said yes immediately, then realised I had no idea what the man looked like.

That’s the whole profession, basically. You know the work, you know the signature, you’ve never seen the face. “It’s the perfect crime,” Avi Steinberg said this week, a decade after drawing him without his knowledge. “You can be famous on paper and still walk around without anyone bothering you.”

Avi kept the caricature. I look at it and see only the mistakes, but he tells me it’s a treasured possession. I’m deciding to believe him.

Ten years, Ten a week.

Avi started submitting to The New Yorker straight out of high school and sold nothing for roughly a decade. I asked whether he hit year seven and wondered if he should pack it in. “I don’t wait till year seven to feel like that…”

The turn came when he worked out what the cartoonists he admired were actually doing. “The greats, they drew a batch of ten cartoons every week. And when I really learned that, my heart sank.” So he gave himself a year of ten a week. No more emotional rollercoaster. At the end of it, he could either do this properly or quit.

He teaches kindergarten in New York City, which is where he gets his best material on artistic confidence. “My students are the best artists in the world. No one told them how not to draw something.”

I told him about being fifteen, getting detention for a savage caricature of my history teacher, then having that same teacher sidle up to my desk during detention and offer me twenty dollars to do a mean one of the retiring school gardener. Avi diagnosed the whole career in one line: being a cartoonist is the balance of being in detention and getting twenty dollars.

Paid to be in trouble. Still true at forty-two.

Then Tom Toro , our official ‘Ryan Seacrest of Comic-Con’ gossip elbowed his way in to the stream

Tom appeared halfway through, still wearing his San Diego Comic-Con lanyard, having got home at half one that morning. He would like to be appointed my official Comic-Con Correspondent. Granted, obviously.

His collection And To Think This Started As A Book Club was up for an Eisner. Then the winners leaked. Comic-Con briefly posted the results on their own website, somebody screenshotted it, and Reddit did the rest. “Not since the Will Smith slap of Chris Rock has there been such a scandal at an award show.”

Tom resisted. Tom failed. He looked the night before, reasoning he would enjoy the dinner more if he knew, and found he had lost to Tom Gauld, “who has the flawless first name of Tom.” He was there with his son and struck a deal: every second book sale converted directly into Pokémon cards. “I basically started asking for payment in Pokémon cards, because that’s what it would be anyway.”

Tom is also up for Gag Cartoonist of the Year at the Reubens, after a Thurber finalist nod and the Eisner. He is hoping to lose all three. “I think it’ll be funnier to go 0 for 3 than 1 for 3.”

Rule of threes. The man is committed to the bit.

Avi’s new book contains an alien character he invented at twelve, posted to the newspaper syndicates, and had rejected. He kept the file for thirty years. “Nothing is ever totally gone. It was very nice to see that the work I did as a twelve-year-old wasn’t a waste.”

He is also banking the small milestones as they arrive: the cover, the proofs, the first box of copies. “However the book sells, whatever the reception is, those things are yours.”

Tom’s verdict on his friend, delivered with real affection: “Avi is like the Aristotle of gag cartoons. Your stick figures coping with the horror of existence is one of my favourite things.” Avi: “My biography.”

Watch the replay, then buy the books.

The full episode is up now. There is live drawing in the back half, and Tom talked his way out of it by claiming he cannot sketch, which I am choosing not to believe.

Avi Steinberg, The Jumble is out 3 November and available to pre-order wherever you buy books. Pre-orders genuinely matter: they all tick over on release day and become the number the publisher looks at.

Tom Toro, And To Think This Started As A Book Club, his Eisner-nominated collection, is out now. His children’s book Between the Balloons lands at Thanksgiving and is also up for pre-order.

Buy them from bookshop.org, from your local, from all of it. As Avi put it: buy one from each place, just to spread it around.

‘til next time!Your pal,

PS. I am up for a Reuben this year in book illustration division for You’re Not a Real Dog Owner Until, drawn with Scott Dooley, alongside two books I own and rate more highly than my own. Morris remains unimpressed, and has been on the drafting table chair since Tuesday.

PPS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

I said at the top of this episode that I didn’t want to call Josh Gondelman a comedian, because the word does about a third of the required work.

Here is the CV, and I have since checked it against his actual bio rather than my memory, which is a courtesy I extend to guests and to no one else. Five years at Last Week Tonight with John Oliver, first as web producer and then as staff writer, where he collected four Emmy Awards, two Peabody Awards and three WGA Awards. Head writer and executive producer on Desus & Mero at Showtime. A contributor to the final season of The Marvelous Mrs. Maisel. Two stand-up specials: People Pleaser (2022) and Positive Reinforcement (2025). A book of essays, Nice Try: Stories of Best Intentions and Mixed Results. Co-creator of the parody Twitter account @SeinfeldToday. A regular panellist on NPR’s Wait Wait... Don’t Tell Me!

We first met about ten years ago at Union Hall, doing Picture This, the show where cartoonists draw live while comedians perform and everyone pretends this is a normal way to spend an evening. I have two deeply unemployable skills: cartoonist and comedian. My parents are thrilled. Picture This is the only place on earth where both of them are load-bearing at once.

Josh’s read on it was better than mine:

“You’re watching something that’s never happened before and will never happen again. Everybody is kind of on edge seeing how the artists will interpret the comedy and how the comedians will react to the art. It’s perfect.”

We also remembered a show where the comic on stage was working a long stretch about diarrhoea, and I, being a professional, had no choice but to render it. Gratuitously. Backstage was a convivial disgrace. We were crying.

That’s the whole show, really. Backstage is better than the stage. (Don’t tell the box office.)

The Overnight Success That Took 9 Years

I confessed that I had followed @SeinfeldToday for years without ever once registering that Josh was behind it. He co-created it with Jack Moore in late 2012: log lines for Seinfeld episodes, were they to exist in the present day, and present day was 2012 into 2013… which is now a period piece.

The numbers are f*****g absurd:

“By, I would say, 48 hours later, it had like 100,000 followers... Never had anything like that happen to me before or since. It was like as close as I had to being Hawk Tuah.”

The Sunday night the account was formed, Josh had dinner with a friend who worked as a manager. She told him, gently, that she loved working with him and would keep helping him out, but that her boss was after clients with a slightly higher profile.

Two days later, the boss wanted a meeting. And to sign him!

“I’ve never seen something turn on a dime like that in my life before.”

He had samples. He’d been doing stand-up for years. But he didn’t have the bulletproof script sitting in a drawer waiting for the world to finally notice him. He had drafts that were “all kind of a little rough.” So the lightning struck, and he spent the next year converting it into late-night writing applications, one at a time, like a man turning a lottery win into a mortgage.

The heat arrives whether or not you’re ready. It doesn’t wait while you tidy up.

The Taste of a 57-Year-Old Father of Three

Nice Try is a collection of essays, and I have described it, to Josh’s face and now to you, as being like “A Kind David Sedaris.” He took the compliment the way he takes everything, which is to say he immediately turned it into an admission of ongoing inadequacy:

“We moved into a new apartment last week and I was just shelving my books and I saw my old copies of Naked... I haven’t looked at it in years, but it was like, I’m chasing that still as a prose writer.”

Same. The personal essay has a king, and we are both loitering outside the palace.

There’s a bit in the book about a childhood library trip and discovering R.L. Stine, and a line about having the taste of a 57-year-old father of three.

“Books were kind of the place where I could have more adult taste. My parents were a little more protective with movies and TV and even violent video games. But with books, it was kind of whatever I could get my hands on.”

Which is how a child ends up with real, considered positions on prime John Grisham. The Rainmaker. The Client. The Firm. He said “prime Grisham” the way other men say “prime Coltrane.” That truly is 57-year-old-father-of-three behaviour.

Writing in Someone Else’s Mouth

Here’s the thing about Josh’s writing that I’ve never been able to get past. Him on stage is him on the page. The voice is identical, and it’s completely unique, and yet he spent five years writing in an acerbic British one, and got four Emmys for it.

How?

Below: how you make an atrocity funny without becoming a ghoul, the word Gary Gulman put in my head that I can’t get out, the pumpkin quiche incident, and why the meanest guy in the room in 2007 was never the one to copy.

“In a good writer’s room, the best writer’s rooms, I think, have real diversity of perspective. And so even when the host is filtering it through how they think and talk and see things, you are bringing what your interests and ideas are when you can get it through the lens of what they do.”

Part of what the host wants, he said, is breadth. He pointed to a Last Week Tonight piece made after his time there, on Black hair care and health, led by Ali Barthwell:

“That’s really cool that John has the range to go, I’m going to figure out how to talk about this thing that is compelling to me even though it is not of my personal experience. And then I want someone like Ali who can go, I can speak to this from personal experience and I can make it sound right coming out of John.”

So it isn’t impressionism. It’s not doing the accent in your head. You learn the show’s keystone phrases and structures and referential touchstones, and then:

“How can I expand this palette in directions, like in vectors, that are fun and specific to me as well?”

Which means that all those weird esoteric tangents, the ones that feel like they’ve been beamed in from a stranger’s dream? Those are somebody’s fingerprints, and if you know the room, you can dust for them.

“Oh, this is about an angry penguin with a whimsical name. And you’re like, well, that’s a Jill Twiss specialty for sure.”

He also recalled an extremely elaborate bit, requiring numerous graphic mock-ups, concerning an ornate sex party at Wes Anderson’s house. Unmistakably Will Tracy, who went on to write The Menu and Bugonia and worked on Succession for its entire run.

Now that I think about it, I’d always been able to spot Asher Perlman on Colbert the same way. There’s a full stop that arrives, and you go: ah. There he is.

Getting Your Fingernails Underneath

I asked him the question I actually wanted answered. At Last Week Tonight, he had to take genuinely bleak news and other material and make it funny. Not funny instead of serious. Funny as the delivery mechanism for serious.

“I think that layer kind of lets you take a couple of harder swings.”

You don’t always mock the tragedy. You mock the discourse around the tragedy. But, he said, it doesn’t always have to be removed levels of commentary. Sometimes the material walks right up and hands you itself:

“Then you see the CEO of the company that did the polluting going, look, you gotta dump sludge somewhere. And you’re like, okay, that we can make fun of. We can make fun of this a*****e.”

Then the second part, which is the best description of comedy writing I’ve heard in a long time:

“Look for the little things where you can get your fingernails underneath and go, oh, I can claw something up here that’s fun and funny, and not just a wry good point.”

Because a very good point that only elicits ‘clapter’ is, as he put it, its own thing. Fine. Applause is not laughter and laughter is not agreement.

“There’s an idea that you can really sink into someone’s subconscious, that they walk away and they’re actually thinking about it going, holy s**t.”

…

“The efforts of these shows are not mostly to change the world. It’s to make things intelligible.”

Not to fix it. To give you the vocabulary and the narrative at your fingertips for a thing you’d half-heard and had a feeling about and couldn’t articulate. Give them the utility. Give them the words.

It’s the same job as a political cartoon, incidentally. You are not passing legislation. You are handing someone a shape for the thing they already felt.

Oliphant knew that. He never wrote for the awards. He wrote for himself, and the rest of us borrowed the shape.

It’s Pronounced ‘Quiche’

Which brings us to the vocabulary people.

Gary Gulman is, to my mind and Josh’s, a master linguist operating under cover of stand-up, and the thing Josh loves about him is the exact opposite of what you’d expect from a man with a large vocabulary:

“He didn’t invent a new word. He did not put words together in a way they’d never been put together before. But he just cut through. Just the emphasis and specificity and structure of, I’m going to use the same words twice in the opposite order. And it gets a huge laugh. To me, that’s like watching surgery.”

I told him I’d watched Grandiloquent thinking the same thing: this is neurosurgery. Fastidious to the point of being slightly frightening. It is not about being baroque or ornate with the construction. It’s the opposite. It’s distillation.

Gary taught me a word recently that I cannot shake. He and Myq Kaplan were doing their thing over lunch, the two of them together, and Gary described the practice of shepherding your sentences. He’d picked it up as a legal term. It means carefully guiding, organising, and directing the flow of your writing so it leads the reader exactly where you want them to go.

And here is where I should tell you that these are the same men who, at lunch on the Upper East Side, destroyed me. I ordered the pumpkin quiche at a vegan place. It arrived within about five minutes, which is barely enough time to make eye contact with a waiter, let alone a quiche.

“Whoa,” I said. “That was quick.” Within half a split second, without looking up, Kaplan said: “It’s pronounced quiche.”

Gary said, " Wow! " in the tone of a man witnessing a hole-in-one, “Kaplan. That mind. He’s so…” and I said, “…Quiche?” Then it was just three idiots laughing at themselves over a vegan tart.

That’s it. That’s the whole reward. Decades of craft, a Peabody or four between us, an entire language at our disposal, and the peak human experience remains three men in their forties and fifties giggling at a homophone.

“The Born to Run of That Thing”

Josh’s stated ambition, which I’d like framed:

“I always joke that I want everything to be the Born to Run of that thing. Just give me all the horns and the bells. Give me all the s**t.”

But then, the caveat that makes it actually true:

“That kind of maximalism of intention, if not of execution, I think is really beautiful. I just want to fill this vessel, whatever it is, whether it’s a book or a song or a painting, with meaning. Whether that means it’s one long brushstroke of varying pressure that communicates it really clearly, or whether it’s a novel that’s 120,000 words. As long as it is the fully realised version of the thing it is, and done with enthusiasm, I love it.”

One brushstroke of varying pressure. He said that to a man holding a pencil, live, on camera, and I don’t think he even knew he’d done it.

“The Attell of It All”

“I think maybe the most copied comedian of all time, or of the last 25 years, is Dave Attell.”

I agree, and I have receipts, because I spent years on the comics’ bench at the Cellar watching him close out the late show, trying to reverse-engineer it. How the f**k is he doing this?? It felt like a magic trick performed in a room full of magicians.

And the second you try to imitate it, you lose something in translation, because there’s a layer underneath that isn’t transferable. There’s no way to do it without simply being Dave Attell.

Josh:

“I’ve heard dozens, if not hundreds, of people where you can draw a straight line from Dave Attell to where they are. But no one that captures...”

The globe joke. I travel so much for stand-up. I used to be afraid to travel, because when I was a kid, my father beat me with a globe. One of my all-time favourites, and one of his.

“I’ve seen so many people change the setup and the punchline by one word. And it’s like, that’s not slick. We know the seed that that’s coming from is so clear.”

The inimitable thing about Attell isn’t the darkness. Josh nailed it:

“The more bleak the comedy gets, the more grimy, having that gentle touch goes so far. This is a person, there’s a sweetness in this person, and they are also willing to look at the grimy parts.”

Which is, incidentally, precisely what makes Aaron Chen work. His special Funny Garden is on Netflix, and it is one of the most singular things you’ll see. So innocent on the surface, and then he picks up a vase to drink from, and takes you somewhere genuinely deep, and you don’t notice you’ve gone.

Josh made a related point about voices being unforgeable. Maria Bamford. Daniel Simonsen, with a thick Norwegian accent that is not, on inspection, Norwegian, or anything else. No one talks like that. Whatever that is, is him.

The Kindest Cut

Here’s what I actually wanted to ask him, and I saved it for last because I wasn’t sure how it would land.

I started in Perth in 2007. Everyone in that scene was watching the same two people: Dane Cook and Louis C.K. Fellow suburban Bostonians, as it happens. And there was a meanness in the water. The comedy rewarded the fastest, meanest person in the room. That was the metric. That was the whole ladder.

Josh started in Boston in 2004, at the actual epicentre, and built an entire career being conspicuously the opposite. I asked whether it was a bit he couldn’t get out of, or genuinely his personality.

“Yeah, that’s exactly what it was. It took me a little extra effort. I started in Boston in 2004, and there were maybe a dozen guys who were like, oh, Dane Cook is what comedy is. And we’re all doing iterations of that.”

A dozen. All of them. Vituperative by default, because that was what winning looked like.

What saved him wasn’t a principle; it was proximity. He got lucky enough to be around the emerging Boston lot: Gary Gulman coming back through on Last Comic Standing. Erin Judge. Lamont Price. Joe List. The Walsh brothers, Chris and Dave, running a weekly show of strange sketch and storytelling that had no business working.

“Seeing that was like, oh, you don’t just have to do the thing that you see most prevalently or most successfully.”

That’s it. That’s the whole thing.

I sat on that bench at the Cellar for years trying to work out how to become Dave Attell, and the answer, which took me an embarrassingly long time to arrive at, was that there wasn’t one. Not because I lacked the technique. Because the vacancy was already filled. By Dave.

Josh worked that out in 2004, in a room full of a dozen men doing iterations of the same guy, and quietly went and did the other thing.

Four Emmys. Two Peabodys. Three WGAs.

Nice try.

Watch the replay, then go subscribe to Josh!

Josh writes That’s Marvelous!, a weekly newsletter of pep talks: for readers, for strangers, and for inanimate objects. He described it in the chat, and I’m describing it here because I’d like you to actually go.

thatsmarvelousnewsletter.com

Also: Positive Reinforcement, his new special. People Pleaser, his first. Nice Try, his essay collection. Wait Wait... Don’t Tell Me!, where he has also guest-hosted. All of it good. All of it kind. None of it soft.

I could have talked to him for hours and was only stopped by the tyranny of the clock and the fact that I was, by then, drawing him.

‘til next time!Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

Over Austin Kleon’s shoulder, the whole time we talked, Lynda Barry watched us.

Not the actual Lynda Barry; an original manuscript page from Cruddy, hanging on his studio wall next to an outtake from Making Comics. He calls them his Guardian Spirits, and the plan is to keep adding to them until he’s got a full pantheon of demigods looming over his desk.

I understand the impulse completely. I’ve got a drawing of Larry David in my studio that Luke Watson painted for me, and he glares at me every day with an expression that says, “Is that really the version you’re gonna go with? Aeeeeh, it’s prettaaay pretty good.”

This was Austin’s second time on Draw Me Anything, and I’d be lying if I said we covered the book in an orderly fashion. We started with 63 people in the chat and ended with 350, which means roughly 287 people wandered in midstream to find two middle-aged cartoonists arguing about whether Hook is secretly a midlife-crisis film.

It is. More on this later. It gets worse. (Bangarang!)

Don’t Call It a Book Tour

The new book is called Don’t Call It Art, and Austin, a man committed to the bit, named the promotional run for it the Don’t Call It a Book Tour. Previous books got 25-city tours. This one got three cities: Austin, Nashville and Cleveland, which he described as “kind of like a straight shot to Cleveland type tour.”

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He slept in five beds in six days. “This is a young person’s game,” he said, and every comedian who’s ever done the road nodded so hard the vertebrae in their necks audibly clicked. The week after a launch, he told me, all the things that keep you alive as a creative person, the sleep, the walks, the daily ritual, go straight out the window. The man who wrote the book on sustainable creative practice blew himself out promoting a book about sustainable creative practice. “I wish the books worked on me better,” he said, which might be the most honest thing anyone has ever said on this series.

Nobody Knows Anything, Confidently

We got into the publishing industry, which Austin summarised via William Golding’s old line that nobody knows anything: true of Hollywood, true of books. Nobody in publishing knows what sells books, he said, “but they’ll say something confidently to you about it.” Everyone’s chasing BookTok, which is lightning in a bottle, on purpose, which is not how lightning or bottles work.

The only thing that actually sells a book, he said, quoting Ann Patchett, is one person holding it up and saying I love this. Word of mouth. That’s it. That’s the whole machine.

And then he reached for Charles Portis, because of course he did. There’s a line in Gringos about two men who “had known the despair of selling things that people didn’t want,” and Austin pointed out that this is the entire creative life. Nobody is asking for another book. Nobody asked for another cartoon. Nobody wanted a live-action Moana. You make the thing anyway, and then you present it, over and over, like Marshawn Lynch running through a man’s chest. Austin apparently plays the Beast Mode clip to himself on a loop when the self-promotion shame creeps in. If you run through somebody’s face, over and over and over and over and over …. eventually they can’t take it any more. This is also, coincidentally, my approach to open mics.

The shame is real, though. You think: my audience must be so sick of hearing about this thing. Meanwhile, an actual paid subscriber to Austin’s newsletter walked up to him in Nashville and said If I’d known you were in town, I’d have brought all my friends. The man works across the street from the hotel. He pays money to be told these things. He did not know.

So no. Nobody is sick of hearing about your thing. They have not heard about your thing.

The Taco Bell Theory of Art

My favourite framework of the day came from, and I want to be clear that I am quoting a bestselling author here, Taco Bell. Austin loves their “distinctiveness rule”: you can change the taste, or you can change the form, but never both at once. That’s how he thinks about his readers. Keep the familiar square format, but fill this book with his kids’ drawings and new textures, so it reads like an Austin Kleon book that was somehow drawn by his children. (This “RED” rule stands for relevance, ease, and distinctiveness.)

He’s unapologetic about thinking of his audience while he works, which felt almost transgressive to hear out loud. “My readers have given me everything,” he said. “This idea that I wouldn’t think about them when I was writing is just weird to me.” His books, he insists, aren’t pure art anyway; they’re the byproducts of him trying to make stuff. The Montel Jordan principle: this is how we do it. Not how you have to do it. This is how we do it.

Neither of us went to art school, which is probably why we both find kids so instructive. They don’t know the correct way to do anything, so they just let it rip.

Why the Book Exists at All

The title comes from a John Baldessari quote: I learned so much about art from watching a kid draw. Kids don’t call it art. They’re not making Art; they’re just doing stuff. There’s a Brian Eno line in the book to match: people do much better when they don’t think they’re being artists. If you don’t call it art, you’re likely to get a better result.

Austin described the book as being for anyone who’s lost that lovin’ feeling: you’ve been doing the work a long time, maybe even successfully, and the joy has quietly left the building. Where Keep Going was about pushing through a world gone mad, this one is Keep Going 2.0: the call is coming from inside the house. The chaos isn’t out there. It’s in here, with the deadlines and the invoices and the creeping suspicion that your passion has become your landlord.

I know this feeling intimately. Twenty-one years as a full-time cartoonist, and people still say “you’re so lucky, you get to do what you love every day,” and I want to grab them by the lapels and explain that they have no idea how hard it is to stay in love with a thing that is actively driving you insane. It’s not drudgery exactly. It’s more like the fruit has started to turn, and instead of leaping out of bed to bite the apple you’re standing in the kitchen at 7am wondering if you can make some sort of bread out of it.

Charlie Bucket’s Midlife Crisis

Which brings me to my Willy Wonka theory, which I made Austin sit through and now you will too. End of the film. Great Glass Elevator. Wonka looks down at Charlie and says, “Don’t forget what happened to the man who suddenly got everything he ever wanted.” Charlie asks what. And Wonka says he lived happily ever after, but what he should say is:

Let me tell you who Myq Kaplan is, because if you’re not already a fan, that changes today.

He’s been doing comedy for going on twenty-five years. He has a Comedy Central special. He was a finalist on Last Comic Standing. He’s been on Comedy Bang Bang and Keith and the Girl more times than I can count. He has two specials on YouTube - AKA and Rini - and a new one he’s just recorded. He runs a Substack called Myq Kaplan's Arty Har-Hars, which you should subscribe to immediately after this. He is one of the most densely packed laughs-per-minute comedians working anywhere in this city, and I say that as someone who has been watching this scene very closely for fifteen years.

He is also the reason I once shot IPA out of my nose at a comedy show on Second Avenue. But we’ll get to that.

The first thing you need to know about Myq Kaplan is that his name is, by design, a barrier to entry.

“I brought it upon myself, obviously, the spelling of my name,” he told me, almost immediately after we started recording. “There’s a little bit of a barrier to entry. But once you get past, then I feel like there’s a lot of reward.”

He then, in the same breath, held up a microphone.

“That’s a Myq” he said.

I say “by design” because everything about Myq’s comedy is by design - the spelling of his name, the precision of his phrasing, the way a simple prop becomes the punchline to a joke that is also, if you look at it properly, a philosophical position about the rewards of paying attention. Nothing is accidental. The commitment to craft runs so deep that it’s become invisible, which is when craft becomes art.

The name story is one I’ve been dining out on since 2014. I was a young, fledgling comedian appearing on a certain popular podcast, and I was doing my plugs at the end of the show. Bob Kelly was hosting. I was reading names off the lineup for an upcoming show - I think it was the Producers Club - and I arrived at Myq’s name, and I said: “and Meek Kaplan.”

The room turned on me. Louis J. Gomez. Dan Soder. Joe List. All of them looking at me with the particular expression that New York comics reserve for someone who has just revealed a catastrophic gap in their knowledge.

“You f*****g Australians,” somebody said. “How have you never heard of Myq Kaplan?” They laid into me for twenty minutes. About my accent. About my ignorance. About the basic expectation that someone doing comedy in New York should know who Myq Kaplan is, which is, I’ll grant them, a fair point.

And then, having absorbed all of this - having been fully educated and corrected and aware - I subsequently introduced Myq on stage that night as “Meek Kaplan.” Again.

Myq received this with extraordinary grace. “Your trauma is my treasure,” he said.

But the real first time I encountered Myq Kaplan was not that night. It was earlier - 2011, or thereabouts. I was still coming to New York as a tourist then, once a year, for a month at a time, in the way that people who are going to end up living somewhere do before they commit to actually living there. I was going to as many comedy shows as I could, trying to understand the scene, sheepishly introducing myself to people and then overthinking every conversation afterwards on the subway home.

The show was called Kabin. It was on Second Avenue, the back room of a bar. Rebecca Trent booked it. It was, by the general consensus of everyone who was there at the time, the best comic hang in the city. Their fifth anniversary show, I think it was, went from six in the afternoon until five in the morning. 11 hours. I was in that room for most of it.

I had a beer in my hand. Sean Donnelly was hosting, or someone like Sean Donnelly. Whoever it was said, with the full weight of insider authority: you are going to love this next guy.

I took a sip.

Myq Kaplan walked on stage and said something. I genuinely do not know what it was. I have never known. What I know is that the beer - an IPA, specifically, which made the whole thing considerably worse - travelled at velocity through my nasal cavity and exited my face in a direction that beer is not supposed to exit. My eyes were streaming from the carbonation. I was making sounds that grown adults should not make in public. Eight minutes later, Myq left the stage, and I was a different person.

It is a trauma-memory. The kind that’s vivid, not because it was bad, but because it was so involuntary. The laugh didn’t ask my permission.

“That’s very, very kind, very thoughtful for you to share,” Myq said when I told him this story on the podcast. “Better than a spit take. Your trauma is my treasure.”

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My drawing board is currently covered in a mix of art supplies and aggressively pungent deli meats.

I’ve got a puddle of Higgins ink dangerously close to a towering pastrami on rye, and my entire apartment smells of mustard. Outside my window, a sanitation truck is violently reversing down 9th Avenue. The floorboards are vibrating. On my monitor, looking entirely too relaxed for a man navigating the crazy New York City culinary scene, sits Ben Gollan, a fellow Aussie expat making a go of it in the big smoke.

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Ben’s the undisputed Sandwich Tour King of New York. He runs a wildly successful walking tour company called ‘A Man and His Sandwich’, where he guides people through the absolute best, most artery-clogging delis in the five boroughs. But the thing that always short-circuits my brain about Ben isn’t his encyclopaedic knowledge of cured meats. It’s his backstory.

It’s always deeply comforting to talk to another expat. We spent a significant portion of the hour just being two Australians with thick accents, complaining loudly about the structural inefficiencies of New York City while simultaneously admitting we’d never live anywhere else.

We got into the gritty reality of the New York hustle. If you’re an Aussie expat, you know the exact cultural whiplash we’re talking about. Back home, we have this insidious thing called the tall poppy syndrome. If you try something outside the box, people immediately try to cut you down. Ben mentioned that when he goes back to Australia and tells people he runs sandwich tours, they laugh and ask what his real job is. But here in New York? People look at him and say, “That’s a great idea, I bet you’re the best.”

The city runs on that delusional, infectious encouragement. It’s the only place where a hungover, out-of-work chef from South Africa can stare at leftover Indian paratha bread and some banh mi scraps in his fridge, accidentally invent a pulled-pork paratha taco, and suddenly end up running three wildly lucrative storefronts. (That’s the true story of Goa Taco, by the way. A legendary Lower East Side staple born entirely out of desperation and a hangover).

As I mentioned, Ben’s a fellow expat Australian. Back in Sydney, he was a crisply dressed corporate lawyer working for the government. He traded the courtroom for the chaotic, unforgiving streets of New York back in 2016, all to support his wife’s career. Somewhere along the line, a single pastrami sandwich at a now-defunct East Village deli completely derailed his professional trajectory. He ate the sandwich, had a culinary epiphany, and decided he was going to dedicate his life to the space between two pieces of bread.

There’s something deeply terrifying about abandoning a stable, lucrative law career to yell about sandwiches on a Brooklyn sidewalk. But it’s the kind of unhinged creative pivot I completely admire...

During our Draw Me Anything session, I set myself the absurd task of drawing a photorealistic pastrami sandwich while we talked. I quickly realised that drawing bread’s a nightmare. Bread’s just a chaotic sponge. You try to capture the crust with pilot pen, and it just looks like a diseased rock.

Ben’s got this incredible, magnetic energy. You can see exactly why his tours are perpetually sold out. The live chat was losing its collective mind over his deli recommendations. You could feel the audience getting hungry through the screen…

There’s a cartoon early in Rich Sparks’s new book of a man my age, alone in a bath, lifting a spoon to his lips. No setup, no crowd, no scene. Just the act, and a title underneath:

“Youp.”

Where I’m from, that’s a diagnosis. My uncle Greg taught it to me as a child: “Mate, get a load of this bloke. He drinks his own fucken bath water.” (Australian for arrogant.) First cousin to tall poppy syndrome, that great national project of never letting anyone tout their own success.

I opened the book to that page first, and decided the next hour of my morning was spoken for. Which is roughly how the whole conversation went.

A book with no thread, which is the whole point…

The reason for the visit was Horseshoes and Tardigrades and Other Drawings, Rich’s new collection, put out by our mutual pal Marty over at The Weekly Humorist. A book of single-panel cartoons is one of the hardest things in the world to assemble, and I say that as someone who has tried. There’s no narrative. No theme. No throughline to hide behind. It’s just a brain, decanted onto a few hundred pages, arranged so a stranger will smile no matter where they crack it open.

I got my copy in the mail the other day. I had mail to sort- urgent, adult, responsible-immigrant mail. Instead of opening my Jury Duty letter, I sat down with the book instead and didn’t move for an hour and a half. Morris watched me from the floor with the quiet judgment of a dog who knows the difference between work and joy and resents being excluded from the second.

Rich works out of Chicago, has been at it for decades, and turns up pretty much anywhere a cartoon can legally be printed- the New Yorker, Air Mail, the lot. The story goes that he got his start redrawing a Ring bell for service sign on the scale in the produce department of a grocery store, then quietly updating it every week until customers started coming by to see what it said. That’s the whole career in miniature, really. Couldn’t not do it.

“Getting a dog right doesn’t mean getting a dog funny.”

This is the line I came away with, and I suspect it’ll rattle round my skull for months. (it’s around the 40:47 mark).

We got talking about reference, because Rich draws his animals from photos. I thought he knew what a dog looked like. Then I spent months -months!— trying to work out the shape a dog makes when it leaps to catch a ball, only to discover that the real anatomy of a jumping dog is so deranged it looks like a printing error.

He personally lands, as you do, somewhere between the truth and the lie.

I quoted the late James Stevenson, the New Yorker cartoonist, who said that “Until you draw a picture of something, you are apt to be dead wrong about what it looks like.” And that’s the trade, isn’t it? You think you know your own father’s face until you try to put it on paper and realise you’ve been carrying around a rough sketch your whole life.

But here’s the bathos (because there’s always bathos). Even after all that fastidious study of the real, Rich’s actual insight is that accuracy isn’t the job. You can chase the truth of a thing for weeks and still have to abandon it at the last second for the funnier pose. There’s a reality inside the panel, and it is not this one.

I think about that with caricature. The likeness lives in the asymmetry- the bit of a face that’s slightly wrong is the bit that’s most them. Same with bodies. Rich said he sees the human form in three dimensions, rotating, and that when genuine symmetry turns up it’s so rare it’s almost shocking to look at. The rest of us are gloriously, correctly lopsided. The algorithm would like to convince you otherwise. The algorithm can drink its own bath water.

Here’s the bit where I rattle the tin.

These recaps take a while. The interview’s the fun part- the writing-up is me, alone, in the studio, doing the cartoonist’s equivalent of drawing the dog’s back leg forty times until it’s both true and funny. It’s a solitary job, as Rich said.

If you’ve read this far, you’re my kind of reader, and I’d love you to consider upgrading to a paid subscription. It’s a dollar a week. That’s less than a single bad coffee in this city, and considerably less than a good one.

It keeps the lights on, the cheap whiskey in the glass, and the bath water in the bath, where it belongs.

The men in the cartoons are all his father.

This was the moment the whole hour tilted.

I’d been banging on about the glasses -Rich draws this specific flat-topped frame, the kind where you can’t see the eyes, and I’d built an entire theory about Scott McCloud, and how a reader projects themselves onto a face they can’t quite read.

Then he said the men in the drawings are his dad. Or versions of his dad. The glasses, the little moustache, the high-waisted trousers, the bit more hair than a man that age has any right to keep. He’s been drawing his father, over and over, for a career.

We didn’t dwell. Cartoonists never do. We pivoted immediately to the fact that he draws nearly everything with a Uniball Vision. Because the ink isn’t waterproof, I sometimes cheat a little wash out of it with a water brush- making it look like I hauled a full watercolour kit to the desk when really I just smudged a pen.

The deep cuts, the dick jokes, and Vlad the Employer

The book is stuffed with what I can only call cartooning deep cuts. There’s a Leonardo da Muncie, a Charlie Brown gag built on the first Peanuts strip ever published. There’s a podcast hosted by a dog that I would, hand on heart, subscribe to over most of the human-hosted ones currently clogging the feed.

And then there’s Vlad.

Rich has a Vlad the Impaler in the book, and seeing it sent me straight back to my own- a Vlad the Employer I drew years ago, the warlord interviewing a candidate, captioned “You start Monday!” I went to enormous, faintly insane lengths to get the costuming, jewellery and spear historically correct, because the New Yorker employs fact-checkers and I wasn’t about to be caught out on the haberdashery of a fifteenth-century warlord.

The joke is stupid. I knew it was stupid. I drew it purely to please myself and threw it into the batch as filler, fully expecting it to make the good ones look better by comparison. It’s the one Bob Mankoff took one look at and said O.K. -which, as anyone who’s submitted a batch knows, is never the one you bet on. You send your bangers and your sacrificial throwaway, and the machine reaches past all of it for the daft one you never meant anyone to see.

We also fielded a chat question from Cartoons by Collins about how on earth Facebook hasn’t banned him, given the, ah, anatomical confidence of certain drawings. Rich’s answer was a masterclass in living with the unknowable: he genuinely doesn’t know whether it’s a buggy AI, a phantom moderation team, or simple cosmic luck, and he’s decided that thinking about it is the surest way to summon it. “I feel like I’m always on the verge of getting in trouble,” he said. I told him that’s a wonderful place to live. I should know. I’m subletting there too.

Chickening out at Disneyland

The detail I can’t shake: Rich has been to the Billy Ireland Cartoon Library at Ohio State (the site of this year’s Reuben awards). It’s the largest cartoon collection on Earth, the actual Disneyland for people like us, originals sitting in flat files like it’s nothing. And while he was there, he spotted the curator Caitlin McGurk behind a door. A social media friend. Someone who’d have been thrilled to meet him. And he got starstruck and couldn’t bring himself to say hello.

When I first moved to New York 12 years ago, I did what every terrified transplant does: I asked other comedians for advice…

This was a mistake, because comedians are a bag of cats and no two of them agree on anything. One told me to do every open mic in the city. One told me to do none of them. One told me, with great seriousness, to “find my inner hobgoblin,” which is the kind of thing people say when they have no actual information to give you and would like you to leave them alone please.

But there was one piece of advice that came back every single time, from every single person, like a liturgical response…

“Go get yourself a Mindy.”

Stop using Facebook photos for your headshot, you absolute disgrace, and go get a real one done by Mindy Tucker.

So I did. That’s how we met. I schlepped to her studio in Brooklyn, helped her haul lighting gear around Williamsburg in search of a wall that wasn’t a condo yet, sweated through a shirt, and carried the gear back up the stairs again. We did things this way because we couldn’t afford a studio, and back then you could still shoot outside before the entire borough turned into guarded glass.

That was twelve years ago. This week, Mindy came on Draw Me Anything, and I finally got to tell a few thousand people what the New York comedy scene has known for two decades: she’s the best there is.

Draw Me Anything is a livestream & podcast about artists, comedians, writers, and the people who make things.

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Here’s the thing about Mindy that took me years to understand. She doesn’t just take a good photo. She gets something out of you that nobody else can.

Comedians are a nightmare to photograph. We’re always on. We’re cracking wise, busting balls, performing, running a bit, because the bit is a shield and the camera is a threat. Point a lens at a comic and watch them deploy their entire personality as a defence mechanism.

Mindy disarms all of it. Her trick, which is not really a trick, is time. She found that comedians needed more time, and that if you gave people time they seemed to calm down and stop being nervous. She gives you a job. She has you help her move a light. And somewhere in the puttering and the “oh wait, stay right there,” the armour comes off, and she catches the actual person underneath.

When I told her this, she explained where it comes from, and it’s the best origin story: Her dad was a chaplain. Not a desk chaplain, a sports chaplain. He’d pray with the team before the game, sit through the game, and if a player got hurt, he’d be the one riding in the ambulance, relaying what was happening back to the church. And Mindy looked at me and said, with total clarity:

“Basically what I’ve done is I’ve taken what my dad has always done, and I’ve added photos.”

It was recently Jim Gaffigan, of all people, who first pointed this out to her. Four years into shooting comedy, he told her: “Your dad’s a preacher*, that’s why you get along with performers, you lived with a performer.” He just read her whole life back to her like a palm. She didn’t fully clock it herself until later. The wax-on-wax-on moment; this realisation that she’d been training for the thing her whole life without knowing it.(*Other famous preachers-turned-comedians include the incredible Sam Kinnison and one-time NYC Regular Justin Smith)

A million of us. In a box.

Now to the actual reason she came on… Mindy’s launched something called Mindy’s Comedy Archives, and you need to understand the scale of it before you understand why it matters:

She has, at last count, over one million photographs. A million. And that number was current as of the day she taped her second and third episodes, so it’s already wrong, and wrong in the upward direction, because she keeps adding to it…

I went on a bit of a tear about this on the show, so forgive me, but: there is no real history of New York comedy. There are scattered special reviews, the odd opinion piece in the Times, a Chortle write-up here and there. But there is no cohesive, visual, living document of this absurdly specific art form in this absurdly specific city.

Except there is. It’s in Mindy’s hard drives.

Last week I had Myq Kaplan on, and we talked about the brutal churn of a comedy career: the bright-eyed arrival, the agent, the manager, the late-night spot, the sitcom, the rollercoaster with no terminus. Myq’s point was that once you realise that’s the career, the constant insane flux, that’s the whole thing.

What Mindy has is that flux, frozen, frame by frame. One comedian over an entire career, from their very first nervous headshot all the way through shows and festivals and late-night spots, and you watch them change. Their posture, their costume, their face. They age. They evolve. Nobody else has documented this the way Mindy has. She did it by accident, one shoot at a time, for twenty years.

The formatis beautifully simple.

A comic comes in and gets handed a box of photos. It starts with the very first photo Mindy ever took of them, and they go in chronological order, telling her as much or as little as they want about what was going on in their career and in the New York comedy scene at the time.

The first episode, out this week, is with Rosebud Baker, and Mindy calls it the blueprint. Rosebud starts in a 2014 group photo, a gaggle of comedians, and by the end they’ve done a Netflix special cover and land on her book cover.

“That’s why we live here.”

The first episode didn’t go perfectly. The blog post wasn’t up on time. The workflow wasn’t sorted. And Mindy’s attitude toward all of it was the thing I keep turning over. She told Rosebud, essentially: it’s not perfect, can you help me get started?

“You cannot write a line of code that replaces the invisible labour, the thousands of terrible rough sketches, and the deeply human derangement required to make a truly great cartoon.”

If you try to launch a print humor magazine in the 21st century, most financial advisors will tell you to just set your money on fire instead; it’s faster, it requires less paperwork, and it keeps you warmer in the winter.

We live in the era of the digital churn. We live in an ecosystem where corporate media conglomerates are continuously gutting their editorial staff, pivoting to video, pivoting away from video, pivoting to AI slop, and generally treating the written word and the drawn cartoon as disposable ephemera. The conventional wisdom is that print is dead…

But if you’ve been reading this newsletter for more than five minutes, you know I am obsessed with the messy, unglamorous back-end of making a living as an artist. I love pulling back the curtain on the creatives who look at the “churn,” laugh, and figure out how to keep the lights on without selling their souls to the algorithm.

This week on Draw Me Anything, I brought in a guy who looked at a sinking ship and decided to build his own lifeboat.

I was thrilled to host the brilliant Michael Gerber. Michael is the publisher, editor, and mastermind behind The American Bystander, a publication that Newsweek literally called “the last great humor magazine.”

During the stream, we dug into exactly how you resurrect a print humor magazine in the 21st century without setting mountains of corporate cash on fire. It is a story of grit, absurd luck, and a publishing model that bypasses the corporate overlords entirely. But before we get to the Chinese oligarchs and the naked Kickstarter launch, we have to go back to a very small room in the One World Trade Center.

The Everest of Cartooning and the Mouse in the Car

My introduction to The American Bystander didn’t happen on a newsstand. It happened in the absolute epicenter of the New York cartooning world.

It was late 2014, maybe early 2015. I was a relatively new immigrant to America, still trying to figure out the brutal mechanics of the New York publishing scene. To my brain, the ultimate peak of the industry -the absolute Everest of cartooning- was getting into MAD Magazine and getting into The New Yorker. Those were the twin pillars of the comedy art world. Everything else was just scenery.

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I was sitting at The New Yorker in the cartoon lounge. Now, let’s be honest about the cartoon lounge at that time: it wasn’t really a “lounge” anymore. It was just a small room off to the side from where cartoon editor Bob Mankoff’s office was located. But the physical space didn’t matter, because of who was in it.

The legendary Sam Gross was sitting in the room. He was positioned right below a giant framed picture of his absolute classic cartoon—the one with the mouse driving the wind-up car. If you’re a cartoonist, sitting in a room with Sam Gross was like a guitarist sitting in a room with Keith Richards.

Sam was holding a copy of a magazine I had never seen before. “Kid, have you heard of this magazine?” he asked me.

I looked at the cover. The unmistakable, beautiful line work of Arnie Roth stared back at me. It was Issue Number Six. “I’m embarrassed to say that I haven’t heard of it,” I admitted.

Sam started explaining what it was, and as he flipped through the pages to show me the cartoons, my jaw hit the floor. I was looking at a murderers’ row of comedy art. “This is everyone I love,” I remember thinking. “These are all my favorite cartoonists in here. What the hell? How long has this thing been around?”

Sam saw the absolute shock on my face. “Yeah, right?” he smiled. “You should submit to this.”

Naturally, the moment he said that, the impostor syndrome kicked in with the force of a freight train. I looked at the names on the pages. I don’t belong in here, my brain screamed. This is ridiculous. These are giants in here. I don’t belong in here.

I was so completely enamored with this magazine, yet I had absolutely no idea it even existed.

When I told this story to Michael on the stream, he just laughed. “Well, that’s kind of the story of the business right there,” he said.

“Everybody loves it. Very few people know about it. We’re always trying to figure out how to get more people to know about it.”

Fast forward to today, and I am deeply proud to not only be a contributor to The Bystander, but to have hosted its “re-founder” to talk about exactly how this impossible publication came to exist.

The Trifecta and the Pitch

To understand The American Bystander, you have to understand the pedigree of the people who originally conceived it.

I am sitting at my drawing board in my sweltering Manhattan apartment. Grant is sitting in his room in Wichita, Kansas. The contrast between our two environments is immediate and palpable.

His background is calm, lined with books. There is a quiet, steady, midwestern stillness to his frame that makes my own neurotic, constantly vibrating New York energy feel unhinged.

I have been a big fan of Grant’s work for a long time. If you have spent any time on the internet looking for art that makes you feel deeply seen, you’ve likely stumbled across his comics. They’re incredibly insightful, minimalist, and poetic. He manages to take complex, abstract concepts like mindfulness, anxiety, the crushing weight of the creative process, and distil them into beautiful, clean, uncluttered panels.

His style is a brilliant amalgamation of influences, echoing the whimsy of Quentin Blake and the neurotic genius of Roz Chast, yet entirely his own. But there’s a detail about Grant’s life that always manages to short-circuit my brain.

Grant is a practising orthodontist.

By day, he is literalizing the mechanics of human smiles. He operates a medical practice in Wichita. He looks into people’s mouths, adjusts wires, and fixes the geometry of their teeth. And if that wasn’t demanding enough, he also has five kids. He is managing a small, highly energetic army of children, running a medical practice, and somehow still managing to be one of the most prolific and poignant cartoonists I’ve ever met.

When you spend your life as a working artist in a city that charges you fifty dollars just to leave your apartment, you tend to view time as a hostile currency. The idea of holding down a demanding, highly technical medical career while simultaneously producing emotionally resonant art feels impossible.

During our session, I had to ask him how on earth he manages it. Does the day job drain the creative battery, or does it fuel it?

Grant’s answer completely flipped my understanding of creative burnout. He explained that his multifaceted skill set is actually the secret engine of his productivity.

“You need some kind of natural reset button. For me, my job where I straighten teeth and, you know, talk to people and, you know, do some good work is part of that for me”.

It’s a deeply reassuring concept. Instead of draining his creative reserves, his orthodontic work acts as a mental palate cleanser. It engages a completely different, highly analytical, physical part of his brain. When he’s adjusting a bracket on a teenager’s molar, he is not agonising over the narrative arc of a graphic novel. By stepping away from the drawing board to do a job grounded in the physical, real world, he allows his creative side to rest, recharge, and process ideas in the background.

We fell into a deep discussion about this, touching on David Epstein’s brilliant book, Range, which argues that generalists -people with diverse, multifaceted backgrounds and varied experiences- often triumph in a specialised world. I mentioned that I was currently reading Epstein’s other book, Inside the Box, which explores the idea of creative thinking within strict confines.

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If you want to test the absolute limits of your nervous system, try sitting in the middle of Times Square with a sketchbook, a pen, and an open microphone...

It is a sensory assault. It does not smell like inspiration; it smells like roasted nuts, diesel exhaust, and the sweat of ten thousand tourists realising they’ve lost their Marriott room key. The noise is a physical weight. Sirens, pedicabs aggressively looping Alecia Keys, and people dressed as off-brand Spider-Man aggressively demanding five dollars for a photo.

“Drawing in New York is combat journalism. You’re trying to capture lightning in a bottle while the bottle is being kicked down Broadway by a guy screaming at his phone.”

But this is exactly why I do this. When I started New York Cartoons, the core promise to you, the reader, was that I wasn’t just going to send you polished, sterile drawings from the safety of an air-conditioned studio. The promise was to show you what living, surviving, and creating in New York City actually looks like. The chaos, the invisible labour, and the absurd encounters that fuel the work.

So, for this week’s episode of Draw Me Anything, I took the studio to the street!

My guest was the brilliant Nishant Jain, better known to his massive audience as The Sneaky Artist. Nishant came down from Canada to sit with me in the blistering epicentre of Manhattan. For an hour, amidst the absolute bedlam of Times Square, we drew the chaos in real-time.

Before the stream started, a tall man holding a brown paper bag whipped towards us before locking eyes with me… it was, of course, my neighbour and pal Anthony LeDonne. Because of course it was. (You can see his SYML entry here.) When I introduced him to Nishant, I’d mentioned we were nerding out about Derrida last time we spoke. When he asked who that was, I knew he’d be in for an education… Nishant gave him a primer on the arsehole French philosopher and his musings. I could see the hamster in Anthony’s brain begin to sweat, then die in a mad panic. Derrida: It’s one helluva conversation starter.

What started as a live drawing session quickly spiralled into one of the most profound, quotable, and vital conversations I’ve had in years. We talked about everything from French philosophy and the existential threat of tech companies to the mindfulness of observation and the stark contrast between Canadian politeness and New York velocity.

Here’s what happens when you put two process-junkies in the loudest intersection on Earth…

Part I: Vancouver VS. New York

There’s a distinct difference in the way a New Yorker observes the world versus the way a Canadian does, and watching Nishant work was a masterclass in pacing.

Nishant possesses a terrifying level of calm. He didn’t fight the chaos. He observed it. “In Canada, the environment gives you the space to think,” Nishant told me, his eyes tracking a guy in a chaotic neon jacket. There is a physical and auditory room to breathe. The silence lets you construct the narrative. But in New York, the noise forces you to react. It’s an entirely different muscle.

He’s right. Drawing in New York is combat journalism. You’re trying to capture lightning in a bottle while the bottle is being kicked down Broadway by a guy screaming at his phone.

But despite the velocity of the city, Nishant’s process is startlingly deliberate. As we talked, he casually built what would become a beautifully complex drawing of the scene. He wasn’t rushing. He was practising what he calls the radical act of paying attention.

“...your body and mind are absorbed in the union of an ask, which is to look to interpret and then to put it down, translate it. And in a lot of ways, you shut out a lot of concerns, you stop thinking about time, you stop thinking about your responsibilities of service, and you're just here for a while.”

Part II: The Mindfulness of the Pen, and the Radical Act of Paying Attention

We spend so much of our time talking about “mindfulness” as this sterile, corporate buzzword. (I’ve written about this before) Tech companies have commodified it. They sell us apps that ding to remind us to breathe, which we check on the same glowing rectangles that are actively destroying our attention spans.

Nishant’s approach to drawing is the exact antidote to this. For him, drawing isn’t about producing a piece of “content” for an algorithm. It is a grounding mechanism.

“Drawing isn’t about making a pretty picture,” Nishant said, his pen moving carefully across the paper. “It is about forcing yourself to sit still in a world that profits entirely off your distraction. When you draw something, you are forced to actually see it. You aren’t just looking at it. You are understanding its geometry, its weight, and its relationship to the things around it. You are acknowledging its existence in a way that taking a photograph never will.”

That hit me like a freight train. In the digital mailstrom, we take thousands of photos we will never look at again. We consume the world in half-second swipes. But when you drag a pen across watercolour paper, you’re making a physical record of time spent. You are saying, I was here, and I paid attention. “The modern world wants us to skim,” he added. “Drawing is the refusal to skim.”

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Part III: Derrida, Language, and the AI Plagiarism Machine

Naturally, sitting in the glowing neon Mecca of American capitalism, the conversation pivoted to the tech overlords and the looming shadow of Generative AI.

If you read my essays, you know my stance on the “AI Slop Machine.” I view it as a cultural parasite. But Nishant brought a deeply intellectual, philosophical lens to the conversation that completely reframed the issue for me. He brought up Jacques Derrida.

For those who skipped French Philosophy in college, Derrida was the father of “deconstruction.” He famously argued that language isn’t just a tool we use to describe reality; language creates the boundaries of our reality. We can only understand the world through the vocabulary we have to describe it.

“Think about what AI actually is,” Nishant explained. “These tech companies aren’t building ‘intelligence.’ They are building predictive language models. They are machines that guess the next word, or the next pixel, based on a massive, stolen dataset of the past.”

He paused to add a shadow to the drawing of an awning.

“If Derrida is right -if language shapes our reality- then handing our visual and written language over to a machine is incredibly dangerous. An AI cannot create a new vocabulary. It can only recycle the old one. It homogenises human experience into an average. It regresses us to the mean.”

This is the exact problem with AI art. It looks perfect at first glance, but it contains absolutely zero humanity. It has no point of view. It doesn’t know what it feels like to sit on a cold metal chair in Times Square while a siren blares in your left ear.

“When a human draws a line,” Nishant said, “even if it’s a wobbly, imperfect line, it contains intention. It contains a decision. The AI slop has no intention. It is just statistical probability masquerading as art. And humans are biologically hardwired to eventually reject things that have no soul.”

He added something that I really wanted to write down for a discussion later:

“...the point of AI is not to make articles; the point of AI is to make an endlessly spinning mill of content to feed their social media algorithms to hypnotise and make you into addicts so that you become a passive consumer instead of a creative.”

Part IV: The Finished Masterpiece

By the end of the 50-minute conversation, my own drawings were a frantic, scratchy, high-energy reflection of the anxiety of Times Square. It looked like New York feels.

But then Nishant held up his sketchbook.

I actually stopped talking for a second. Look at that, I said on the stream. It was incredible. This guy had just casually, while dissecting French deconstructionism and the ethics of tech conglomerates, built the most insanely beautiful drawing of the intersection.

It wasn’t just a rendering of buildings and tourists. It had life in it. You could see the deliberate choices he made -what to include, more importantly, what to leave out, what to emphasise. It was the absolute antithesis of an AI-generated image. It was a physical artefact of a human being paying deep, mindful attention to a chaotic world.

Watch the Full Replay…

Reading these quotes and clips is only half the experience. If you want to actually see the process -if you want to hear the sirens, see the pen hit the paper in real-time, and watch two working artists navigate the muck of New York City while talking about the survival of human art, you need to watch the replay.

This is the promise of New York Cartoons. I don’t hide the process. I don’t put a filter on the reality of this job. The full, uncut, 50-minute video replay of our Times Square drawing session is available right now for paid subscribers.

When I first sat down to chat with Jeremy Caplan about artificial intelligence and digital productivity tools, I genuinely did not think we would end up talking about him playing the violin. I certainly did not expect the conversation to pivot into a deep, philosophical appreciation for the irreplaceable magic of humans sitting in a room together, simply enjoying a live performance.

But tha’s the funny thing about talking to someone who spends their life evaluating machines. You inevitably end up talking about what it means to be human.

The frictionless technological utopia we were promised feels increasingly like a relentless, exhausting deluge. Every week brings a new platform to master, a new algorithm to appease, and a new artificial intelligence threatening to automate us into oblivion. It’s like drinking from a fire hose while someone yells at you to “pivot to video!”

This is exactly why I was so incredibly relieved to sit down with Jeremy on this episode of Draw Me Anything.

Jeremy is a rare beacon of sanity in the digital miasma. He is the Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. He is a former journalist for Time Magazine. Before that, he was a classical violinist. But more importantly for my own daily survival, he is the creator of the massively popular Wonder Tools newsletter on Substack. Jeremy spends his days wading into the chaotic, deeply overwhelming waters of the internet. He tests, breaks, and reviews new apps, software, and digital features so the rest of us don’t have to waste our precious human hours doing it.

Distilling the Chaos

We kicked off the stream talking about the exhaustion of trying to keep up with tech news. It is not just about discovering new tools anymore. It is about tracking the constant, aggressive updates to existing tools. ChatGPT has a new voice feature. Gemini just launched a massive update. Claude is now doing something entirely new with your phone. And you can’t opt out of it.. It never stops.

Jeremy explained that his superpower for distilling this madness down to accessible, bite-sized pieces actually came from his time writing for Time for Kids. When you have to explain complex global news to an eight-year-old in exactly one hundred words, you learn to cut the jargon immediately. You learn to anticipate a human reader’s questions and preemptively answer them.

He also cited the legendary tech writer Walt Mossberg as a major mentor and influence. Mossberg succeeded wildly at The Wall Street Journal because he approached technology not as a deeply entrenched engineer, but as an ordinary guy just trying to figure out how a tool could actually be useful in his daily life.

“I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone…”

That is exactly what Jeremy does with Wonder Tools. He doesn’t just list fifty new AI tools that launched on Product Hunt this week. He gives you three specific, highly actionable ways to use one feature of NotebookLM to make your Tuesday slightly less miserable. He gives you templates. He shows you what a forty-page deep research report from Gemini actually looks like, so you do not have to spend twenty minutes generating one just to see if it is useful.

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Evergreen Processes over Disposable News

One of the most fascinating things about Jeremy’s approach is his focus on evergreen content. We’re constantly blasted with disposable news. A tech CEO gets fired, a new app launches and dies in a week, a company changes its name. Jeremy actively avoids the daily churn. He wants to create resources that a reader can save and return to three weeks later, knowing the information will still be fundamentally useful.

This really resonated with me. I told him about a post I wrote on Medium over a decade ago. People constantly ask me how I manage to juggle cartooning, stand-up comedy, writing, and running a business without completely losing my mind. The answer is timeboxing. I work strictly from a calendar, not a to-do list. I estimate how long a task will take, block it out in my iCal, and adjust the time block later if it took longer or shorter than expected.

I wrote a simple, straightforward piece explaining this exact process. I thought it was old news. Cal Newport had written about it years prior. But the piece went incredibly viral, and I made two thousand dollars from the Medium partner programme purely off that one specific workflow explanation. Sometimes the most valuable tools are not shiny new apps. Sometimes, they are just fundamentally sound ways of organising a chaotic human brain.

The Ethical Calculus of AI

We eventually had to talk about the elephant in the room. Artificial intelligence…

I frequently get accused of being either a doomer or a total Luddite, but the truth is, I am an early adopter. I was one of the very first cartoonists in my circle to embrace Wacom tablets, Cintiqs, and the iPad Pro. I actively test out tablets for companies like Xencelabs. I do not shy away from folding digital tools into my workflow when they help automate the absolute drudgery of administrative freelance life.

However, the rapid acceleration of generative AI requires a lot of mental arithmetic. I told Jeremy about my personal ethical boundaries. I use Grammarly for proofreading. I am currently experimenting with Gemini for deep research. But I absolutely refuse to use Meta AI or Elon Musk’s Grok because I fundamentally distrust the ethics of the people building them. I opt out of the platforms where I find the creators ethically compromised.

Putting these streams together, wrangling brilliant guests, manually untangling the spaghetti bowl of a brain to pull out the best insights, and writing these recaps requires a heady cocktail of intense caffeine and sheer willpower. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the time and labour of writing these up, and keeps Morris supplied with the unnecessarily expensive dog food he demands…

Jeremy had a fascinating, highly pragmatic take on this. He acknowledged the massive macro issues. He is deeply aware of the environmental cost of data centres, the terrifying water usage, and the flawed predictive models being used to evaluate people in hospitals and prisons. But he treats his newsletter strictly as “service journalism.”

He used a brilliant restaurant analogy. When we go out to eat, we sometimes evaluate the ethical supply chain of the ingredients, the working conditions of the farmers, and the environmental impact of the transportation. But other times, we just need to eat a sandwich because we are hungry. He doesn’t believe we need to litigate the macro ethics of AI every single time we try to automate a tedious spreadsheet or fix a typo. He leaves the heavy investigative journalism to the experts, specifically citing Karen Hao’s brilliant book Empire of AI, and focuses entirely on practical utility.

The J. Jonah Jameson Editor

I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone.

Because I no longer work in a physical newsroom, I deeply miss having a ruthless editor. When I was coming up in newspapers at nineteen years old, I had a classic, cantankerous, ink-in-his-veins editor. He was a J. Jonah Jameson type who had absolutely no compunction about telling me my work was complete garbage. It hurt my precious feelings constantly, but I learned faster than I ever would have with a polite sycophant.

Since I can’t afford to hire a human to yell at me in my apartment, I built a custom AI editor in Gemini. I programmed it with the specific persona of a grumpy, hard-assed, chain-smoking newspaper editor. Now, when I finish a draft by hand, I feed it to the bot. It yells at me about my weak verbs, my terrible grammar, and my overly long paragraphs. I ignore half of its advice because I know the rules well enough to break them, but it forces me to actively defend my choices.

Jeremy agreed completely. He relies heavily on Claude Projects for his micro-editing. He feeds it all of his past writing to establish context, background, and tone, and then uses it as a highly critical sparring partner to catch redundant phrasing and double commas.

He pointed out a provocative but entirely true reality. There are incredible human editors out there. But the average human copy editor simply doesn’t have the bandwidth, the time, or the willingness to ruthlessly tear apart paragraph four and analyse your four different verb choices on a Tuesday night. An AI will do it instantly, comprehensively, and without worrying about hurting your feelings.

Drawing by Hand Before Hitting Undo

This brings us right back to the violin. We talked about where different artists draw the line with these tools. I brought up a story from a previous stream with Liza Donnelly, the brilliant New Yorker cartoonist. She mentioned using AI purely as a brainstorming partner to bounce ideas around.

Our mutual friend, the wonderful British cartoonist Alex Hallatt, heard that and decided to try it. Alex took some scattered, messy notes from a walk, fed them into an LLM, and started riffing on gag premises. It was a great, highly functional workflow. Right up until the bot cheerfully asked, “Do you want me to draw this for you?”

That is the exact moment the panic sets in. It is the moment you realise the tool wants to replace the human element entirely.

I firmly believe that the wobble in the line, the physical imperfections, and the distinct human voice are the only things keeping us from being completely swallowed by the generic digital void. When young students ask me if they should learn to draw on an iPad, I always tell them absolutely not…

Learn to draw by hand first. Learn the absolute fundamentals with ink and paper. If you draw a bad line with a Hunt 101 dip pen, you cannot hit undo. You have to draw that exact line forty-five times until you get it right. You need those neural pathways to form, and you need to understand the physical mechanics of the craft, before you start relying on digital safety nets. You have to learn how to play the instrument before you let a computer tune it for you.

I spent the rest of the stream doing exactly what I love to do. Drawing wobbly, imperfect lines while navigating the absurdities of the modern world. I am deeply grateful for guys like Jeremy who do the heavy lifting in the digital trenches so I can safely retreat to my analogue drafting table.

Now, if you will excuse me, I need to go figure out why Adobe is demanding another subscription fee.

‘til next time!Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

The Tools We Discussed

* Wonder Tools: Jeremy Caplan’s brilliant, incredibly useful Substack newsletter. If you are overwhelmed by tech, start here.

* Claude Projects: Jeremy’s preferred tool for maintaining context and generating ruthless micro-editing feedback.

* Gemini: The engine behind my custom J. Jonah Jameson editor, and a powerful tool for deep research generation.

* NotebookLM: A fascinating tool for organising notes and research that Jeremy frequently writes actionable guides for.

* IA Writer: A beautifully simple, distraction-free writing tool Jeremy relies on.

* Grammarly: My go-to for catching the embarrassing typos that slip through the cracks at 2:00 AM.

* Wacom & Xencelabs: The digital drawing tablets that keep my freelance career afloat.

The Processes We Discussed

* Timeboxing: The absolute lifesaver of a scheduling method where you work strictly from blocked-out calendar chunks rather than a sprawling to-do list.

* Macro vs. Micro Editing: Understanding the difference between fixing a structural narrative flaw (macro) and tightening up a weak verb in paragraph three (micro).

* Custom AI Personas: Training an LLM with a specific voice and set of instructions to act as a specialised sparring partner for your writing.

Resources and Artists Mentioned

* Cartooning in the Age of AI: Alex Hallatt’s incredibly thoughtful Substack documenting her journey and boundaries with digital tools.

* Liza Donnelly: Legendary New Yorker cartoonist and previous DMA guest.

* Walt Mossberg: The legendary tech journalist who proved that writing for the ordinary user is far more valuable than writing for the engineers.

* Cal Newport: The author of Deep Work and a champion of timeboxing.

* AI Snake Oil: The book by Arvind Narayanan and Sayash Kapoor that Jeremy’s new Wonder Tools book club is tackling first.

* Bird by Bird: Anne Lamott’s absolute bible on the excruciating, beautiful process of writing.

If you joined me last time I had the legendary Kevin “KAL” Kallaugher on the stream, you’ll remember we discussed the “Cartoonist’s Paradox”- the absurd reality where cartooning is incredibly easy to start, but absolutely impossible to stop once it gets its hooks into you. This time around, our conversation shifted gears. Instead of talking about how to get into the game, we talked about how to survive it. We dug into how to stay sane in a politically fractured world, how to defend the analogue line against the digital horde, and the sheer mechanical joy of making marks on paper.

I frequently have moments during these streams where I completely forget I’m hosting a broadcast. I find myself just sitting there, slack-jawed, realising how profoundly lucky I am to have an hour to pick the brains of my absolute heroes. KAL is a legend of the medium. He is coming up on his 50th year at The Economist and is currently putting together a massive retrospective exhibition of his work. Getting to draw alongside him is a ridiculous privilege.

The Outsider’s Advantage: We kicked things off by talking about the absolute circus of modern politics. KAL and I both know what it’s like to be an expat trying to explain American madness to the rest of the world. KAL spent a decade living in the UK, and he noted that being an outsider gives you a unique, clear-eyed view. You aren’t tethered to the deep-rooted tribalism of the country you’re in. You can look at the idiocy on both sides of the aisle and criticise it without feeling like a traitor. It’s a perspective he brings to The Economist, which he praised for its critical thinking and reasoned assessment of global madness.

The Human Line vs. The Human Centipede: We eventually touched on the unavoidable elephant in the room: AI and the internet’s right-wing “meme wars”. KAL pointed out a fundamental difference between a viral meme and a great political cartoon: a cartoon is signed. You know a human being sat down, thought about it, and drew it. In an era of increasing detachment and digital takeover, a hand-drawn line stands out because it has life, energy, and personality.

Or, as Paul Nesja so poetically put it in the live chat: “AI is to creativity as the human centipede is to fine cuisine”. (We probably could have ended the broadcast right there.)

Putting these recaps together requires a unique cocktail of intense caffeine, squinting at my monitor, and manually untangling the spaghetti bowl of my brain to pull out the best insights. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the labour of writing these up, and keeps Morris supplied with the good dog food he has foolishly become accustomed to.

The Magic of Crosshatching: KAL is an absolute surgeon when it comes to crosshatching. He explained that the technique really evolved out of necessity in the 19th and 20th centuries. Printing in colour or half-tones was prohibitively expensive, and newspapers used terrible, cheap newsprint that made ink bleed. Cartoonists had to use juxtaposed fine lines to denote colour, shading, and texture. KAL even talked about the maddening challenge of using hard black lines to crosshatch something as airy and shapeless as a sky.

Diagon Alley for Cartoonists: My favourite story of the stream was KAL explaining where he gets his dip pen nibs. Back when he lived in London, an art director sent him to Philip Poole, a legendary pen dealer on Charing Cross Road. KAL found a tiny, unmarked door squished between two buildings and walked into a dark, heavily wooded room filled with tiny drawers of nibs. He described it as disappearing into Harry Potter’s Diagon Alley.

A hunched, cantankerous guy in a white trench coat shuffled out and started handing him nibs to try. KAL eventually settled on the George W. Hughes 1319. Years later, when he tried to order more, the guy informed him they hadn’t been manufactured in 150 years. KAL eventually got a box of 144 of them, and he is still drawing with them today.

The 5-Line Rule: We talked about the difficulty of line economy—knowing when to stop drawing and not overwork an image. KAL told a brilliant story (often attributed to Phil May or R.O. Blechman) about a cartoonist getting confronted by editors in a pub.

The editors complained that the cartoonist was paid an awful lot of money, yet his latest cartoon only had seven lines in it.

The cartoonist replied: “If I could have done it in five lines, I would have charged twice as much”.

Thanks for tuning in!‘til next time!

Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

The Tools We Talked About:

* George W. Hughes 1319 Nibs: KAL’s unicorn tool of choice. Good luck finding them; they haven’t been made in a century and a half.

* Hunt 101 Imperial: My wobbly weapon of choice.

* Duo-Shade Board: The chemical-laden drawing board that old-school tabloid guys used to use to pull out different shading tones.

The Artists We Discussed:

(Warning: Clicking these links will result in a minimum three-hour Wikipedia rabbit hole.)

* David Levine: The absolute master of crosshatching and caricature.

* James Gillray: The godfather of the political cartoon. His work was so biting that the Royals used to send people to buy out his entire print run just to hide the drawings.

* David Low: The brilliant New Zealand cartoonist who ended up on Hitler’s kill list for his work.

* Ronald Searle: The man whose inky fingerprints are on the style of almost every modern cartoonist alive.

* R.O. Blechman: Legendary graphic designer and illustrator (and possible originator of the 5-line story).

* Paul Rigby & Bay Rigby: The Australian father/son duo who dominated the NY Post and Daily News tabloid cartooning wars.

* Pat Oliphant: The Aussie who brought the energetic, sprawling tabloid style to America.

* Bill Mitchell & Peter Broelman: Absolute masters of Australian editorial line economy.

* Catherine Woodman-Maynard: The Minneapolis graphic novelist who launched “Comics for Change” in response to local tragedies.

Other Resources:

* KAL’s Substack: If you aren’t subscribed to KAL yet, fix that right now. He is generously opening his sketchbooks and sharing a lifetime of process and wisdom.

* Comics for Change: The initiative started by Catherine Woodman-Maynard that gathered over a thousand entries worldwide.

Now, if you’ll excuse me, I need to go see if I can find a guy in a white trench coat hiding in a London alleyway…

I live in an ancient little apartment a block from Times Square, because I love cooking dinner in my bedroom.

It’s more of a ‘Pre-War Cupboard’ really. I ordered a mini fridge the other day because I needed a guest bedroom. Morris, my French bulldog, is asleep on a pile of discarded drawing paper, completely unbothered by the fact that his gourmet kibble requires legal tender. My radiator clangs with the aggressive rhythm of a stolen Citibike being dragged backwards down a flight of subway stairs.

It’s a very particular kind of anxiety. You want to make art, but you also want to occasionally eat a Chipotle burrito (strictly no beans). It’s an impossible Venn diagram. I’ve made my living for twenty-one years as a freelance artist and comedian. I don’t have a day job, I don’t have a side hustle, and I don’t have a wealthy patron bankrolling my Blackwing addiction.

Luckily, Mason Currey came on the show this week. He’s the author of Daily Rituals, a book I devoured during the pandemic, and his new hardcover is out right now. It’s called Making Art and Making a Living: Adventures in Funding a Creative Life.

When I first saw the title, I told Mason my immediate thought process. “I initially, when I got the book, thought it was finding a creative life,” I said. “And I was like, oh no, it’s way more important. Funding! It’s about money.”

We got into the weeds of how historical geniuses paid their bills, and honestly, it’s comforting to realise they were mostly just flailing around like the rest of us.

I started by asking about Arthur Schopenhauer, who managed to dodge a soul-crushing life in mercantile finance solely because his father died and left him an inheritance. I spend half my time wandering the concrete canyons of Manhattan, wondering how to pay my rent, so I had to ask Mason: Is the secret to artistic genius really just having a rich dad who dies at the exact right time?

“James Joyce, for instance, was an absolute nightmare of a human being…”

It turns out, the answer is a complicated ‘yes and no’. We discussed Charles Baudelaire, whose letters to his mother sounded violently familiar. I’ve always carried this quiet, crushing shame that I can’t just sit at a desk at 9:00am and produce brilliance. I struggle with regulating attention on demand and initiating tasks without a heroic amount of friction. When I can’t meet expectations, it feels intensely personal, like a reflection of who I am at my core.

I asked Mason if Baudelaire’s legendary financial chaos was a symptom of executive dysfunction. Mason pointed out that Baudelaire would let pressure build up until he was in a mad panic. “He talks about how he can’t make himself do the thing until it’s built up so much pressure that he finally does it in this explosion,” Mason said. “He sort of had run up so much debt that he’s forced to dodge creditors and continually be moving from place to place.”

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Leaving things until the absolute last second to manufacture adrenaline is a textbook symptom of ADHD. Baudelaire didn’t have the diagnostic criteria to explain his dopamine dysregulation, but he had the frantic, desperate energy of a man trying to outrun his own brain. He blew his inheritance, dodged his landlords, and begged his mother for loans just to buy firewood.

“The odd jobs that used to support young artists have basically evaporated… They’ve been swallowed up by algorithms and artificial intelligence.”

We talked about the absolute absurdity of how some artists survived their financial ruin. John Cage funded his avant-garde music by going on an Italian television quiz show as an amateur mushroom expert. (As one does). He won the modern equivalent of ninety grand and bought a Volkswagen van. I asked, "Are we all just one weird reality TV appearance away from funding our next creative project? Do I need to go on a baking programme and pretend I care about fondant just to afford fresh watercolour pans?” (I’m kidding. I did that already…)

Then there’s Fernando Pessoa, who inherited a hefty chunk of change. Did he invest it sensibly to live off the interest? Hell No! He blew the entire inheritance in less than a year, having an incredibly expensive printing press shipped from Spain to Portugal, of course…

We also spoke about the absurd methods we use to force ourselves into a productive headspace. For sixteen years, the only way I could get my daily newspaper comic strip done was a highly specific, slightly unhinged ritual. I told Mason all about Scotch Bath Sunday. I would get in the bathtub, pour myself a generous glass of peaty Scotch, and sit there with a yellow legal pad. No phones, no iPads, no laptops. Just me, the boiling water, and the looming terror of a deadline.

Mason loved it. “I think there is a little bit of superstition there,” he said, “but there’s also something really powerful about the repetition. You train your mind to get into that particular headspace on a somewhat regular basis.”

Margreet is a brilliant Dutch comic artist and the former Comics Laureate of the Netherlands. She spent three years acting as an ambassador for the medium, literally compiling guides to help teachers get graphic novels onto high school reading lists. She is also someone who intimately understands the frantic reality of a creative life.

The Court Jesters & the Freedom Fighters

Margreet and I talked about the bizarre cultural divide in cartooning. In Australia, people generally look at comic artists like we are overgrown toddlers playing with crayons. It is treated as a silly little hobby. But if you take a train to France or Belgium, comic artists are treated like absolute rock gods.

I told her about a cartooning conference I went to in France called RIDEP. I was standing in a room with cartoonists from Tunisia, Sudan, and China. They had been exiled or forced into hiding for drawing anti-propaganda cartoons against dictatorial regimes. They were actual, literal freedom fighters. I draw jokes about talking dogs. I realised very quickly that I am more of a court jester. It was a profoundly humbling reality check.

Making a living as an artist requires you to constantly ask people for money, which is something most cartoonists are fundamentally terrible at doing. Margreet is an expert in crowdfunding, having run multiple successful campaigns in Holland to bypass the traditional publishing gatekeepers.

The Kickstarter Scam…

But she recently got targeted by a very clever, highly sophisticated Kickstarter scam. Scammers will pledge a massive amount of money to your campaign just to get your attention. Then, they send a highly convincing email from a “notification bot,” claiming your account is suspended, and your money is frozen. They provide a link to steal your credentials. Margreet described it as the digital equivalent of being lured away from a busy high street into a dark alley. We are already sweating over our drawing boards; we do not need thieves making it harder.

Related viewing:

My interview with the Founders of Zoop:

Theology and Annoying Mrs Lee

Margreet has a fascinating background. She originally flunked out of school because she hated the technology, so she pivoted to studying theology at the University of Amsterdam. Both of her parents are ministers, so it was in her blood. While she was there, she drew a comic for the faculty paper called The Adventures of Jesus. (Which sounds like the working title for The Bible).

I completely related to her fascination with religion as a storytelling mechanism. I went to an Anglican high school, and I used to infuriate my Bible study teacher, Mrs Lee. I would sit in the back, drawing cartoons and interrogating the text with the obnoxious persistence of a discount detective. I just wanted to know how the plot holes were resolved. Mrs Lee did not appreciate my feedback. She hated me.

The 3:00 AM Eyeball Hack

The absolute most valuable thing I took away from our chat was a neurological trick for my broken, sleep-deprived brain. We were talking about meditation and dealing with anxiety, and Margreet told me about an EMDR-style hack she uses when she is trapped in a rumination loop.

If you want to read about my annoying high school Bible study questions, a completely bizarre neurological hack to cure insomnia, and the absolute hazard of using a dip pen in bed, consider upgrading to a paid subscription for just $1 a week. It keeps the ink flowing & Morris fed.

Episode Links: Book // Socials // Podcast // Website

If you caught this chat live on Thursday, you know my chat with Sarah Elizabeth Hill didn’t bother with small talk. We dove straight into the deep end.

Sarah writes, produces, and runs Bobi Media. She took $400 and built it into an agency that works with Oscar winners, Deepak Chopra, and brands you see on billboards. On paper, it looks like she just levitated to the top of New York media. Spoiler: nobody floats in this city. You claw your way up, or you get chewed up.

But on Draw Me Anything, we don’t do glossy. We go straight for the mess under the sink. We talked about the invisible sacrifices—the stuff nobody puts on LinkedIn. The reality of trying to keep a business alive in a city that’ll eat you for breakfast if you blink.

Here are a few things we unpacked in the first half of the conversation…

The Reality of the Creator Grind

Turns out, creative brains are actually built for business… if you can keep the lights on, swallow your pride, and remember to actually send the invoice. We talked about those early days, stretching that initial $400 investment, and the sheer, unadulterated panic of realising you are the only safety net you have.

But that same tunnel vision required to build something out of nothing? It’ll burn you out faster than a …ugh. I’m too exhausted. I can’t think of a simile.

Sarah didn’t sugarcoat the human cost of the hustle. She talked about the time the grind nearly broke her completely:

“I was working so much I wasn’t leaving my desk... I hadn’t developed my habits and so was hospitalised, because I couldn’t get my brain to stop spinning.”

Building the “Infrastructure” of You

When your brain is your business, a breakdown isn’t just a personal crisis; it’s a corporate bankruptcy. We talked about the absolute necessity of building a team. And I don’t just mean hiring a virtual assistant. I mean building the infrastructure of you: Accountants. Therapists. The guy who tells you to stop staring at the screen and breathe. All of it.

Sarah made a brilliant point about treating your physical and mental health like non-negotiable client meetings. If you don’t carve out an hour to lift something heavy, walk around the block with the dog, or just stare at the ocean on a Friday afternoon, you’ll crash. The city doesn’t care. The algorithm doesn’t care. You have to work to live, not the other way around.

The “Hell Yeah or No” Rule

New York is an all-you-can-eat buffet of opportunities, which means the most dangerous thing you can do is say “yes” to everything. We dug into Derek Sivers’ famous rule: if it’s not a hell yeah, it’s a no.

“You have to protect your time like it’s the last glass of water in the desert. If you don’t aggressively filter what comes across your desk, you end up building someone else’s dream while yours slowly starves.”

The only way to keep your time from getting mugged by every shiny offer is to know your “Big Why.”

The Reframe, the Churn, and the AI Survival Guide

In the second half of the stream, we got into the stuff that actually keeps you up at night. The heavy hitters. The things we usually only talk about at the bar after the gig is over.

We cracked open the New York Churn- the endless, exhausting loop of people showing up, burning out, and getting spit back out to the suburbs. Sarah handed me a new way to look at the concept of “personal sacrifice” that completely rattled my brain. It made me rethink what it actually takes to stick around, keep your friends, and build a life here that doesn’t fall apart the second the rent goes up.

And then, we finally wrestled with the elephant in the room: Generative AI.

Sarah’s new book, Chat Sh!t Crazy, is all about using these tools to sharpen your sense of self, not erase it. Instead of complaining about the robots taking our jobs, we got into the weeds on how to use AI as a mirror for your own blind spots. We talked about how to survive the AI flood without losing your soul (or your rent money.)

To my free subscribers: If you want the whole thing -the raw, uncut hour- you’ve got to step inside the studio. The full replay is for the folks who keep the lights on and put dog food in Morris’ tummy.

If you care about real art, the messy back-end of the creative process, and actual human connection, I need you in the inbox. Upgrade your subscription. Help keep this thing alive so I can keep bringing you these conversations.

The sheer logistical terror of running a comedy festival is not something the average person truly understands.

You have to convince nearly a hundred highly neurotic, sleep-deprived stand-up comedians to travel to a single location. You have to make sure they get picked up at the airport. You have to house them. You have to pray they have the personal o…

If there’s one thing I’ve been banging on about this week more than anything, it’s that finding a genuinely distinct visual voice in the modern cartooning landscape is brutal.

You need to be instantly recognisable. You need to be deeply funny. You need to build a world. (Oh, and try to make a living doing it.) Tom Chitty has built an entire universe. He is a British cartoonist based in Toronto, a regular contributor to the New Yorker, and an absolute master of the absurd and whimsical (okay, ‘silly’). His characters feature blocky bodies, wide stances, and an otherworldly charm. We sat down for Draw Me Anything yesterday to decode the mechanics of his highly specific, deeply funny brain.

Here is exactly how he builds his worlds…

The Serial Killer Sketchbook

Young artists obsess over perfect sketchbooks. They paint immaculate, highly composed spreads and post them online. It is a complete lie. Real sketchbooks look like the manifesto of a deranged serial killer. Look at the horrendous s**t I just found when I flicked open one of mine…

Tom learned this the hard way in animation school. A tutor looked at his work, told him to stop designing, and ordered him to just start generating ideas. he dropped the pressure of making a pretty picture. He started treating his drawings like handwriting. He now keeps a sketchbook on hand constantly, capturing raw, unfiltered nonsense. Six months later, he opens the book and finds completely forgotten, bizarre ideas that actually make him laugh.

You can’t force inspiration by sitting down and staring at a blank piece of paper. Taking a leaf out of every great artist’s book, he walks to the coffee shop every morning after dropping his son at school. Moving through the world and seeing the horizon literally dislodges ideas from the deep dark recesses of your skull.

The Regret of the “Send” Button

Pitching cartoons is an exercise in psychological torture. You curate a batch of ideas. You arrange them like you are sequencing a Radiohead album. (Yes, we’re exactly the same as Thom Yorke. Thank you.) You convince yourself the order matters. Then you hit send on the email.

The regret is immediate. You look at the batch two hours later and see nothing but glaring flaws. You wonder why you ever picked up a pen in the first place.

Tom survives this weekly cycle by treating it as a boot camp. He gets up, generates ideas, and commits to the sheer volume of the work. Early in his career, veteran cartoonists Matt Diffee and Bob Mankoff gave him ruthless, honest feedback. The ultimate lesson is simple: Do not draw what you think the New Yorker ‘wants’. Draw what makes you completely unique.

Ghost League Baseball and Wonky Parsnips

Tom is launching a Kickstarter on April 1st for an absolute masterpiece. It is called Nooks and Crannies of New York. It is compiled from the fictional chronicles of an eccentric explorer named Baron von Schoogenheimer.

The book is a staggering achievement in world-building. It took him three and a half years to draw. He documents Ghost League Baseball teams, including the Mysterios and their star pitcher Hodge Wang, famous for his penguin-wing throwing action. He documents subterranean trolls making furniture in the interborough tunnels. He draws Roof Mables, who live in disused water towers and help New Yorkers retrieve lost memories.

He grounds the absurdity by pulling from his own family history. He turns a childhood memory of eating Dutch Speculaas biscuits into an elaborate drawing of Schneek’s Belgian magic pedal-powered hot dog production cart.

He also understands the phonetic rhythm of comedy. Some words are just inherently funny. Tom used to run a website dedicated entirely to words with intrinsic humour value. Balloon. Spoon. Guff. Wonky parsnip. He injects this phonetic absurdity into every character name and fictional contraption he draws.

The Caboon and the Fly Ball

Halfway through the stream, we flipped the cameras and started scribbling. Tom uses a Staedtler 0.3 fineliner to achieve his incredibly detailed, controlled line work. After a suggestion from Hue Walker of a Frog on a Bat, he and I began drawing a Caboon, which is a feline-looking primate from his book that accompanies French Canadian taxi drivers to judge the character of potential passengers.

Meanwhile, the live chat was throwing out prompts. Paul Nesja suggested drawing the above-mentioned frog catching a fly ball. I sketched it out, immediately regretting my lack of reference material for amphibian anatomy. Drawing live while trying to conduct a coherent interview is basically an extreme sport, but it forces you to rely entirely on your muscle memory.

Wrestling with glitchy streaming software, fighting the algorithm, and writing these detailed process breakdowns requires a heady cocktail of caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Tom and me drawing live, please consider upgrading to a paid subscription for just $1 a week. It keeps the inkwell full, repays the massive labour, and keeps Morris supplied with the treats he demands.

We are actively fighting a deluge of generic, machine-generated content. You need to support live, human artists who spend years crafting weird, beautiful things. Go to Kickstarter on April 1st and search for Nooks and Crannies of New York. Back the project. Buy the book, and the folks at The American Bystander's Viral Load. Support the absolute necessity of being silly.

Now, if you will excuse me, I need to go burn my sketchbooks before the detectives arrive...

‘til next time!Your pal,

Jason

Tools and Resources We Yapped About Today:

Trying to succeed as a cartoonist is stupid. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. Emily Flake does both, and she makes it look infuriatingly easy.

My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.

The Alt-Weekly Education

Finding your voice requires failure. You need a low-stakes environment to make mistakes, draw weird things, and test boundaries. For Emily, that was the Baltimore City Paper.

She drew a strip called Lulu 8Ball for the alt-weekly. Alt-weeklies are dead now, which is a massive cultural tragedy. They gave artists absolute freedom. Emily figured out a four-beat joke structure, she honed her timing, and she cussed profusely. The traditional papers would never allow that. She is now bringing Lulu 8 Ball back to life on her brand-new Substack. Subscribe to it immediately please and thank you:

The Fraud Detector (Joke in a Box)

Writing jokes is a terrifying puzzle. I arrogantly assumed I knew exactly how to write one. Then I opened Emily’s physical card deck, Joke in a Box.

I read the exercises. I immediately realised I am a total fraud. The prompts are ruthless, practical, and highly effective. Fellow cartoonist Hillary Fitzgerald Campbell actually used the deck to write a joke and ended up selling a cartoon to the New Yorker. You can still buy this box of magic on Bookshop. Do not buy it on Amazon to fund a billionaire’s joyride.

St. Nell’s and the Ghost Hotel

Williamsport, Pennsylvania is a lumber town. It has haunted hotels and a bizarre vacuum of silence. It is also the home of St. Nell’s…

Emily bought a house out there during the pandemic after heading out there and staying in the haunted 100+ year-old hotel, The Genetti, as a little getaway to save her family from murdering each other in their sleep. Her husband told her they had absolutely no money for a second house, so she launched a Kickstarter and raised fifty grand. She turned the property into a free writer’s residency for women and marginalised genders. Three residents stay at a time for two weeks. They write, they sleep, and they create incredible work.

She even launched an entire comedy festival out there called Nellsfest. The town actually shows up and supports the artists. It is a brilliant community. (A lot of medical professionals, as it turns out.)

Longtime readers will remember our eventful booksigning event there earlier this year:

Hell Gigs and Toddler Jazz

Stand-up comedy is an exercise in public humiliation. We brought Hillary Fitzgerald Campbell onto the stream to discuss the absolute worst gigs we’ve ever survived (with emotional scars).

Hillary’s hell gig involved abruptly stopping a family jazz festival. The organisers forced three women to tell dirty jokes to a room full of toddlers. It is the textbook definition of a comedy nightmare.

Emily performed at a children’s play space in Stroudsburg. The audience consisted of exactly one woman sitting on a couch. The woman only spoke Spanish. She stood in a cavernous echo chamber, speaking English into a microphone taped to a stand with packing tape, essentially making bird noises.

My personal hell gig took place in a Williamsport bar. A massive basketball game played on the screens right next to the stage. The bartender connected her phone to the venue’s Bluetooth speakers. She forgot to turn off her keyboard sounds. I tried to tell jokes while the aggressive tap, tap, tap of her text messages blasted through the sound system… more below:

Boxing and Bombing

Getting punched in the face and bombing on stage are the exact same physical sensation.

Emily boxes. I box. Will Sylvince at the Comedy Cellar boxes. The overlap between comedians and fighters is massive. When you take a hit in the ring, it is not the pain that ruins you. It is the disorientation. You have to force your brain to stay in the game while you are completely compromised.

Comedy is identical. When a joke dies, the room turns hostile. You have to stay entirely in control while you are deeply uncomfortable. You eat dirt, you respect the hustle, and you get back up… I’ve written about this before:

Wrestling with glitchy streaming software, cutting through the digital noise, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Emily and Hillary drawing live, please consider upgrading to a paid subscription for just $1 a week.

Thank you Andi Penner, chris eliopoulos, Bear Edwards, Ann Feild, PJ Pierce, and many others for tuning into my live video with Alex Hallatt! Join me for my next live video in the app.

Some notable quotes from this week’s episode:

* “We can’t just be blinkered and think, ‘Oh my God, as creatives, this is an existential threat, and we have to stop it, because we’re not stopping it. It’s like the internet, but bigger.”

* “You can continue doing what you’re doing, the way you’re doing it, but you better be bloody good because you’re going to become an artisan.”

* “You don’t pay the plumber for banging on the pipes, you pay him for knowing where to bang.”

* “Cartoonists die at the drawing board.”

* “AI is coming like the printing press came for monks and illuminated manuscripts. Do you think the monks were pissed off or do you think they were relieved?”

Today’s Draw Me Anything featured the return of the brilliant Alex Hallatt, creator of the syndicated strip Arctic Circle and the Substack Cartooning in the Age of AI.

Alex joined us from Dorset, UK, where the weather is currently “not very lovely,” which is British for “apocalyptic.”

We dove straight into the giant robotic goblin in the room: Artificial Intelligence. Alex approaches this topic with a “scientist brain” (she used to work in clinical research), which makes her perspective refreshingly pragmatic. Instead of just panicking, she’s looking at how to survive. She compared the current AI panic to the early days of digital photography, when old-school photographers insisted it wasn’t “real” photography. Now, shooting on film is an “artisan” pursuit. The lesson? If we want to keep drawing by hand, we’d better be bloody good at it, because we are all becoming artisans now.

One of the funniest moments came when Alex described how she uses AI to handle the “tedious” stuff, like finding the secret service menu on her storage heaters, so she didn’t have to pay an engineer £200 to push three buttons. It’s the “plumber analogy”: you’re not paying for the button pressing; you’re paying for knowing which button to press. And right now, AI knows where the buttons are.

We also talked about the “enshittification” of platforms like Amazon, where search results are now buried under AI-generated guidebooks and sponsored slop. It’s getting harder for independent creators to be found, which is why building a direct relationship with readers (like on Substack) is the only real lifeboat. As Alex put it, “I want to have a chat... human connection has real value in an AI world.”

\While I was going back and re-listening to this episode to write the recap below, I wrote down so many gems that she shared- tips I will honestly keep with me forever. This was a really great conversation. I hope you find it as valuable as I did.

I am currently setting a new personal record for the number of times I can wash the same load of laundry without ever putting it in the dryer.

I think I’m on wash number five. I put the clothes in, turn the machine on, walk away, immediately forget the machine exists, and then remember three days later when the super tells me the basement has started smelling like a wet golden retriever that has been trapped in a swamp. So, I wash them again. And the cycle continues.

This is what having an adult ADHD brain actually looks like. It’s not just being a little “flighty” or getting distracted by shiny objects. It’s a relentless, exhausting daily battle with your own executive function. It’s opening an email, deciding you don’t have the emotional bandwidth to answer it, marking it as “unread,” snoozing it to tomorrow, and then doing that exact same sequence of events 49 more times over a two-week period.

This is also why my chat with Jenny Lawson on yesterday’s Draw Me Anything was less of an interview and more of an aggressively validating group therapy session.

Jenny Lawson (thebloggess) has been writing online for over 15 years, and she has a new book coming out on March 31st called How to Be Okay When Nothing Is Okay: Tips and Tricks That Kept Me Alive, Happy, and Creative in Spite of Myself.

I got an advance copy, and I genuinely could not put it down. Have you ever read a book so good you run out of sticky notes?

It is a wildly funny, deeply vulnerable survival guide for anyone whose brain is a slightly hostile work environment. Jenny and I both share a potent daily cocktail of ADHD, anxiety, and an inability to perceive the passage of time. (I currently have nine clocks in my apartment, and I am still late to everything I have ever attended.) Here are a few of the brilliant, sanity-saving things we talked about during the stream, including why you should always strive to be a Murder Potato.

2. Humour As a Means of Defanging Hard Things

Jenny and I both use comedy as a coping mechanism. We talked about how, when terrible things happen, humour is the only way to genuinely process the grief.

“I think humour is super helpful for me,” Jenny said. “If I can laugh at something, instead of this enormous monster, it becomes like a little bit smaller, a little bit easier to understand.”

It’s an on-ramp. If you write about crushing depression, anxiety, or mental illness, people who don’t suffer from those things might immediately put the book down. But if you make them laugh, it invites them in. It tells them that the stakes aren’t going to crush them.

“If you make somebody laugh, first of all, you invite them in, and you say, ‘It’s okay. It’s not that serious, even when it’s serious,” Jenny explained. “A lot of people who have either reached out to me and said, ‘I read this because it was funny. And then later, years later, when I found myself in depression for the first time... I could go back and be like, oh, okay, I’m not alone.’”

2. Rejection Sensitivity & Farting at the Queen

If you have ADHD, you likely suffer from Rejection Sensitive Dysphoria (RSD). This means you spend a terrifying amount of your day convincing yourself that everyone secretly hates you.

“I constantly am sure that I have said something wrong, done something wrong. I overthink, I second-guess,” Jenny confessed. “The amount of work that I do in my head... it is exhausting.”

You leave a conversation, and ten seconds later, you are meticulously replaying every word, convinced you offended someone. You assume if a friend hasn’t texted back in four hours, they have legally disowned you. You live in a constant state of wondering, “Are we fighting? Are you mad at me?”

Jenny’s friend gave her some advice that completely short-circuits this panic. She asked Jenny to try to remember the last time she saw someone else completely mortify themselves in public.

Jenny couldn’t think of a single time.

“She was like, ‘No, what it really is, is everyone is constantly doing it. But you’re only paying attention to yourself,” Jenny told me. “Nobody is paying attention to how I fed something up because they’re way more worried about the thing that they fed up.”

This led us to my absolute favourite chapter in Jenny’s entire book, brilliantly titled: But Did You Fart at a Queen?

It turns out, there is a historical account from the 1600s of the 17th Earl of Oxford. He was bowing to Queen Elizabeth, and while doing so, he let out a massive, echoing fart. He was so intensely mortified by this bodily betrayal that he literally imposed a seven-year exile on himself. He left the country for seven years. When he finally returned, the Queen greeted him and said, “My Lord, I had forgotten the fart.”

She didn’t even remember. She had a country to run; she wasn’t thinking about his flatulence.

So, the next time you lie awake at 3:00 AM sweating over a slightly awkward joke you made to a barista, just ask yourself: Did I fart at a Queen? No? Then I’m doing fine.

3. The Spoon Theory (and Budgeting Your Sanity)

Trying to explain executive dysfunction to a neurotypical person is like trying to explain calculus to a golden retriever. They just tilt their head and look at you blankly. “Why don’t you just do the thing?” they ask.

If you want to hear about the Spoon Theory (and how to explain your exhaustion to a neurotypical person), Shirley Jackson’s brilliant method for handling internet trolls, and why you should aspire to be a Murder Potato, upgrade your subscription below. It costs less than a bodega coffee, and it ensures I can eventually afford a dryer that actually works.

I spent an hour yesterday talking to Elijah Woolery and Aarron Walter from the Design Better podcast, and by “talking,” I mean I went on several extended, caffeinated tangents about the existential dread of artificial intelligence, my masochistic love for 19th-century stati…

Thank you Beth Spencer, asher Perlman, Alex Hallatt, Margreet de Heer, chris eliopoulos, and many others for tuning into my live video and asking questions of my guest Kyle Beaudette! Join me for my next live video in the app.

I have a confession to make. I keep a secret folder on my computer. It’s not what you think, but it is deeply weird. It’s just labelled “Kyle,” and it is filled with screenshots of drawings by the Canadian artist Kyle Beaudette.

Whenever I’m feeling uninspired, creatively blocked, or just generally annoyed by the blank page, I open the Kyle folder. It is full of wobbly lines, strange creatures, and a frankly alarming amount of beautifully rendered bodily fluids.

Yesterday, I finally got to open the folder and talk to the man himself on Draw Me Anything. Kyle joined me from the frozen expanses of Canada (a fellow Commonwealth resident) for a conversation about the creative process, the horror of social media and AI Art, and how a tin of brown watercolour paint accidentally ruined his life.

Kyle is one of those infuriatingly talented people who didn’t even go to art school. He studied theater, and then spent a decade teaching himself how to sculpt by hanging out on an internet forum run by two brothers from Texas. For years, he was making these incredibly intricate, Tim Burton-esque sculptures. But the pivot to drawing happened in the most unexpected place: a middle school classroom.

As a substitute teacher, Kyle realised he needed a way to connect with the kids fast so he wouldn’t just be “the weird man that they don’t respect”. So, he sat down with a black pen and started drawing with them. He made a rule for himself: no pencils. He would only draw in pen, force himself to make mistakes, and then force himself to live with them. It was an exercise in embracing the mess, and it completely forged the “consistently wobbly” style he has today.

He achieves this signature wobble, by the way, by holding a tiny 01 Micron pen completely straight up and down while shaking his hand slightly. It’s a technique that his teachers tried to train out of him, which is exactly why it works so well.

But my absolute favourite story from the stream was the origin of his most popular subject matter: poop. A few years ago, Kyle’s mother bought him a beautiful Daniel Smith watercolour tin for Christmas. He opened it up and was horrified to find it was a landscape palette, absolutely loaded with different shades of brown. Thinking he had no use for them, he jokingly decided to use the browns to paint a gross picture of a turkey pooping.

People loved it. He did it again. Before he knew it, he was the internet’s premier artist of gastrointestinal distress. He also shared a pro-tip for the aspiring scatological artists out there: if you use Quinacridone Burnt Orange, it scans with a reddish tint, leading concerned followers to constantly advise him to see a gastroenterologist. This is the kind of high-level artistic insight you simply cannot get at RISD.

We also talked about the heartbreaking reality of having your brilliant, original ideas crushed by history. Kyle recently published a gorgeous book called The Garden Witch. Initially, he planned to build 50 sets and photograph his sculptures for it, like a lost stop-motion film. When that turned out to be a logistical nightmare, he asked the publisher if he could just do it in watercolour and ink instead. They said yes, and asked if he knew how to paint with watercolours. He lied, said yes, and immediately started frantically Googling videos of Quentin Blake.

He wanted to combine Blake’s loose, scratchy line work with the sheer narrative insanity of William Steig. He poured his heart and soul into the project. Then, a month before he finished, he discovered that Quentin Blake and William Steig had actually collaborated on a book together years ago. It’s called Wizzil, and it’s about a witch who looks exactly like his character, right down to the frizzy hair. He said he completely “died inside,” which is the only appropriate reaction to finding out two legends already casually dashed off your magnum opus decades ago.

While we talked, we drew. I whipped up an “amoeba unicorn” that slowly morphed into a bat because I accidentally gave it a pig nose. We also fielded a request from the chat to draw a pigeon getting chased by one of Kyle’s creatures, which naturally ended with the pigeon pooping itself.

Hi friends,

This conversation is so important for people to hear, so I’ve decided to remove the paywall on the replay. Please feel free to share it with anyone you think might find it useful to hear.

Your pal,

Jason

---

Join me for my next live video in the app on Wednesday 25th @ 12pm when I speak with fellow New Yorker cartoonist and author, Liza Donnelly.

But first, the recap…

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to.”

That was the line that stuck with me after yesterday’s Draw Me Anything. It was spoken by Patrick Chappatte (Chappatte Cartoons), one of the most respected editorial cartoonists in the world, and it perfectly encapsulates the strange, suffocating atmosphere of 2026.

I was joined by Patrick (who joined us from Geneva) and the legendary US-based cartoonist Ann Telnaes for a 45-minute conversation that was less of an artist chat and more like a war room briefing. We had over 600 people tune in live (a record for this show!), which tells me that I am not the only one feeling the need to huddle together for warmth around the glow of a screen.

If you missed it, above is the full replay (for paid subscribers) and a breakdown of what we discussed. And we discussed a lot.

My Guests

If you are new here, let me briefly introduce the titans I was sharing a screen with:

* Ann Telnaes is a two-time Pulitzer Prize-winning editorial cartoonist. She was a staff cartoonist at The Washington Post until early last year, when she resigned after a cartoon was spiked- a canary in the coal mine for the media landscape we now find ourselves in. She now publishes independently on Substack, where her work remains as sharp, elegant, and devastating as ever. (She also revealed a little secret during the stream: she is still using an old-school metal animation disc from the 1980s to create her work!)

* Patrick Chappatte is a globetrotting cartoonist whose work has appeared in The New York Times, Le Canard Enchaîné, Der Spiegel, and countless others. He is also the Chair of the Freedom Cartoonists Foundation in Geneva. He has a unique talent for “comics journalism” -reportage drawn on the ground- including a recent interactive piece for Le Temps about the surreal spectacle of Donald Trump taking Davos “hostage”.

The Conversation: “Obeying in Advance”

We spent a lot of time talking about their upcoming book, Censorship (or Self-Censorship) in America. The book has already been published in French and is coming out in German, but (tellingly) they are still in negotiations for a U.S. publisher.

Why? Because, as Patrick noted, American publishers seem terrified of inviting the wrath of the administration.

This led us to the core theme of the chat: “Obeying in Advance.”

As Patrick explained:

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to... It’s the people in charge, the editors, the publishers, the media owners, all those guys doing the job in advance. You don’t need censorship anymore. Because self-censorship will do the job for you.”

We discussed the recent incident involving Stephen Colbert and Texas Representative James Talarico, where a segment was reportedly suppressed—a classic example of corporate cowardice disguised as editorial discretion. Anne pointed out that this isn’t just about media control; it’s about the administration’s fear of losing its religious base. Talarico, a devout Christian who believes in the separation of church and state, represents a threat to the monolithic narrative Trump relies on.

The “Gábor Pápai” Warning

Patrick shared a chilling story about Gábor Pápai, a Hungarian cartoonist who won the Courage in Cartooning Award. Papay warned them years ago:

“If you guys in the United States or in Europe get to elect the populists... you’re going to follow the same path that we are following.”

Papay has been sued by his government and called a “cockroach” on national television. Patrick noted that while every country is different, the pattern—using the legal system to harass critics, demonising the press, and slowly eroding norms—is universal.

The U.S. has now fallen to #57 on the press freedom index, sandwiched between Sierra Leone and Gambia. As Patrick put it: “I’m not hopeful that the U.S. is going to go up in this context in the foreseeable future.”

The Immigrant Experience

One of the most moving parts of the conversation was when we touched on our shared status as immigrants. I am an Australian-American; Anne is Norwegian-American; Patrick is Swiss-Lebanese with an American son born in New York…

We talked about the dehumanising rhetoric being used against immigrants- the “animals,” the detention centres, the “denaturalisation” task force that is now reportedly targeting naturalised citizens.

Anne was visibly angry:

“I cannot tell you how angry this makes me... I’m a naturalized citizen just like you... He is definitely running on fear. That’s how he got into office in the first place.”

Patrick added a heartbreaking observation about how the world now views America:

“It’s a broken love. That’s the feeling in the rest of the world. Because there was so much goodwill toward the United States and its values. And the cruelty... it’s really sad.”

Why You Need to Follow Them

We ended on a note of solidarity. We are all feeling the squeeze—whether it’s the algorithms, the publishers, or just the general atmosphere of dread. But as Anne and Patrick proved, the only way through it is to keep drawing, keep publishing, and keep supporting each other.

Please, go subscribe to their Substacks. They are doing the work that the legacy media is too afraid to do.

* Ann Telnaes on Substack

* Patrick Chappatte on Substack

And thank you to everyone who tuned in. It felt important.

You can buy their new book here or in the U.S. at these bookstores:

Lectures de France Inc (Chicago)Foreign Book Source (Chicago)Bonjour Books (Kensington)French Books OnlineFrench & European Publications (New York)Librairie Albertine - Alliance Française of New York|Pierre International Bookstore (Tamarac)World of Reading (Atlanta)

‘til next timeYour pal,

Related Viewing:

* DMA#25: Ann Telnaes on the Power of the Pen (and Why She Left The Post) – My conversation with Ann from last year, before the election, which now feels like a lifetime ago:

Thank you Kevin KAL Kallaugher, Stan!, Paranormal Cartoons, Christopher Thornock, Cat Wilson RN, and the 600+ others who tuned into my live video with Ann Telnaes and Chappatte Cartoons!

Join me for my next live video in the app on Tuesday 24th @ 12pm when I speak with fellow New Yorker cartoonist and author, Liza Donnelly.

But first, the recap…

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to.”

That was the line that stuck with me after yesterday’s Draw Me Anything. It was spoken by Patrick Chappatte (Chappatte Cartoons), one of the most respected editorial cartoonists in the world, and it perfectly encapsulates the strange, suffocating atmosphere of 2026.

I was joined by Patrick (who joined us from Geneva) and the legendary US-based cartoonist Ann Telnaes for a 45-minute conversation that was less of an artist chat and more like a war room briefing. We had over 600 people tune in live (a record for this show!), which tells me that I am not the only one feeling the need to huddle together for warmth around the glow of a screen.

If you missed it, above is the full replay (for paid subscribers) and a breakdown of what we discussed. And we discussed a lot.

My Guests

If you are new here, let me briefly introduce the titans I was sharing a screen with:

* Ann Telnaes is a two-time Pulitzer Prize-winning editorial cartoonist. She was a staff cartoonist at The Washington Post until early last year, when she resigned after a cartoon was spiked- a canary in the coal mine for the media landscape we now find ourselves in. She now publishes independently on Substack, where her work remains as sharp, elegant, and devastating as ever. (She also revealed a little secret during the stream: she is still using an old-school metal animation disc from the 1980s to create her work!)

* Patrick Chappatte is a globetrotting cartoonist whose work has appeared in The New York Times, Le Canard Enchaîné, Der Spiegel, and countless others. He is also the Chair of the Freedom Cartoonists Foundation in Geneva. He has a unique talent for “comics journalism” -reportage drawn on the ground- including a recent interactive piece for Le Temps about the surreal spectacle of Donald Trump taking Davos “hostage”.

The Conversation: “Obeying in Advance”

We spent a lot of time talking about their upcoming book, Censorship (or Self-Censorship) in America. The book has already been published in French and is coming out in German, but (tellingly) they are still in negotiations for a U.S. publisher.

Why? Because, as Patrick noted, American publishers seem terrified of inviting the wrath of the administration.

This led us to the core theme of the chat: “Obeying in Advance.”

As Patrick explained:

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to... It’s the people in charge, the editors, the publishers, the media owners, all those guys doing the job in advance. You don’t need censorship anymore. Because self-censorship will do the job for you.”

We discussed the recent incident involving Stephen Colbert and Texas Representative James Talarico, where a segment was reportedly suppressed—a classic example of corporate cowardice disguised as editorial discretion. Anne pointed out that this isn’t just about media control; it’s about the administration’s fear of losing its religious base. Talarico, a devout Christian who believes in the separation of church and state, represents a threat to the monolithic narrative Trump relies on.

The “Gábor Pápai” Warning

Patrick shared a chilling story about Gábor Pápai, a Hungarian cartoonist who won the Courage in Cartooning Award. Papay warned them years ago:

“If you guys in the United States or in Europe get to elect the populists... you’re going to follow the same path that we are following.”

Papay has been sued by his government and called a “cockroach” on national television. Patrick noted that while every country is different, the pattern—using the legal system to harass critics, demonising the press, and slowly eroding norms—is universal.

The U.S. has now fallen to #57 on the press freedom index, sandwiched between Sierra Leone and Gambia. As Patrick put it: “I’m not hopeful that the U.S. is going to go up in this context in the foreseeable future.”

The Immigrant Experience

One of the most moving parts of the conversation was when we touched on our shared status as immigrants. I am an Australian-American; Anne is Norwegian-American; Patrick is Swiss-Lebanese with an American son born in New York…

We talked about the dehumanising rhetoric being used against immigrants- the “animals,” the detention centres, the “denaturalisation” task force that is now reportedly targeting naturalised citizens.

Anne was visibly angry:

“I cannot tell you how angry this makes me... I’m a naturalized citizen just like you... He is definitely running on fear. That’s how he got into office in the first place.”

Patrick added a heartbreaking observation about how the world now views America:

“It’s a broken love. That’s the feeling in the rest of the world. Because there was so much goodwill toward the United States and its values. And the cruelty... it’s really sad.”

Why You Need to Follow Them

We ended on a note of solidarity. We are all feeling the squeeze—whether it’s the algorithms, the publishers, or just the general atmosphere of dread. But as Anne and Patrick proved, the only way through it is to keep drawing, keep publishing, and keep supporting each other.

Please, go subscribe to their Substacks. They are doing the work that the legacy media is too afraid to do.

* Ann Telnaes on Substack

* Patrick Chappatte on Substack

And thank you to everyone who tuned in. It felt important.

You can buy their new book here or in the U.S. at these bookstores:

Lectures de France Inc (Chicago)Foreign Book Source (Chicago)Bonjour Books (Kensington)French Books OnlineFrench & European Publications (New York)Librairie Albertine - Alliance Française of New York|Pierre International Bookstore (Tamarac)World of Reading (Atlanta)

‘til next timeYour pal,

Related Viewing:

* DMA#25: Ann Telnaes on the Power of the Pen (and Why She Left The Post) – My conversation with Ann from last year, before the election, which now feels like a lifetime ago:

The Watercolour Control Problem with Jessie Kanelos Weiner

Earlier this year, I joined Jessie Kanelos Weiner —artist, author, and watercolour wizard—for a live chat about colour, chaos, and why watercolour refuses to obey. She just released Thinking in Watercolour, which made me realise I mostly think in panic, and snacks.

This year, for 2026, she’s launching a series: 31 Days of Watercolor! which sounds really fun.

In our talk, Jessie asked how I approach colour, and I admitted that I approach it sparingly. I used to think “real artists” painted every shadow like da Vinci. Then I saw the da Vincis at the Met and thought, Yeah… I don’t need to do all that. These days, I use colour the way comedians use silence—strategically. A dab here, a spot there. Enough to make you look where I want you to look.

We talked about the Philadelphia Eagles poster I illustrated—a parody of the classic New Yorker cover, except it’s a jacked football player instead of Eustace Tilly. They wanted bold colour. I gave them subtle pastels amid the team’s green hue. They said, “Brighter!” I spent two days repainting and relearned my favourite rule: colour should serve the joke, not the marketing department.

Growing up in Perth, I had almost no access to great art—just beach paintings and dial-up internet. So I learned from cartoonists like Roz Chast, Richard Thompson, and Ronald Searle, whose trauma and humour somehow coexisted in ink. My grandfather gave me Searle’s book after surviving a POW camp, so I guess drawing as coping runs in the family.

Jessie and I agreed: restriction is, in fact, a form of freedom. Fewer colours, fewer brushes, fewer excuses. Watercolour is chaos in liquid form, and the sooner you stop trying to control it, the more alive it becomes.

I’m still working on that part—the unclenching. But at least now, when my washes go rogue, I can say: It’s philosophy.

‘til next time, your pal,

✏️ Thanks for reading New York Cartoons. To support more mess disguised as art, consider becoming a paid subscriber.

Thank you Kevin KAL Kallaugher, asher, Margreet de Heer, Dan Collins, Pat Coakley, and many others for tuning into my live video with Tom Toro (and his cat, Pumpkin!) Tom is a New Yorker cartoonist, author, and the rare person who can make me feel simultaneously inspired and completely inadequate about my cartooning skills.

His new book, And to Think We Started as a Book Club, just dropped, and it’s already Andy Borowitz’s October Book Club pick. The title itself is a gag from one of his cartoons—bank robbers mid-heist, one holding a crowbar (originally a shotgun, but weapons get flagged by algorithms, apparently). It’s the kind of unwieldy-but-funny title that works because the joke sustains it.

The Art of Drawing Worse

One of the best moments came when Tom shared Bob Mankoff’s advice to Paul Noth: “Draw worse.”

Not as an insult, but as a direction. Noth’s early work was so detailed—cross-hatching, filigree, the whole nine—that Mankoff told him the jokes were strong enough to carry simpler art. The delivery needed to be cleaner. Tom admitted he sometimes overdoes drawings when he’s insecure about a joke, like he’s compensating. I felt seen. Very seen.

“The best thing about your work is the worst thing about your work,” Mankoff once told me. “You draw too well sometimes.” I’m still not sure if it was a compliment. Probably not.

Fact-Checking V*ginas & Left-Handed Catchers

The New Yorker fact-checks cartoons. Tom once got a note asking if he could make a drawing “less vaginal.” (Three lion manes forming an unfortunate composition.) “I had a baseball cartoon flagged because I’d drawn a left-handed catcher—apparently, there hasn’t been one in the majors since 1972. They let me keep it, but wanted me to know.”

These notes are rare, which makes them oddly precious. “It’s nice to know there are eyes on it,” Tom said. Most of the time, cartooning is just the Roman Coliseum—thumbs up, thumbs down, see you in twelve years.

AI Can’t Make Good Mistakes

We talked about AI creeping into cartoon spaces, and Tom’s theory hit hard: AI can’t make good mistakes. It can mimic, reproduce, even generate six-fingered hands by accident—but it can’t make the artful mistakes that lead you somewhere unexpected. The kind that gives a drawing its heartbeat.

“Maybe it’s incumbent upon artists to keep pushing ourselves to realms of discomfort,” he said, “where we just make more beautiful mistakes.”

That’s the hope. That’s the work.

Tom’s on tour all month—Powell’s in Portland this Friday, then Connecticut, New York, Boston. If you’re near any of those spots, go hear him talk and get your book signed. Support cartoon collections. Raise all boats.

‘til next timeYour pal,

Referenced in the conversation:

* Tom Toro’s website

* And to Think We Started as a Book Club (Tom Toro)

* The Borowitz Report (Andy Borowitz)

* Well, This Is Me (Asher Perlman)

* The Joy of Snacking (Hillary Fitzgerald Campbell)

* Understanding Comics (Scott McCloud)

* Matt Inman / The Oatmeal on AI

* Civics 101 Podcast

* Powell’s Books, Portland

* St. Nell’s Writer’s Residency (Emily Flake)

I went into this episode of DMA expecting the usual blend of cartooning shop talk and digital doodling. What I got was a deep dive into creative authenticity, delivered by someone who's figured out that being yourself is both the hardest and most obvious solution to every artistic problem.

The Eugene Empire

Asher's Hi It's Me Again had just dropped, and our conversation naturally gravitated towards his most famous creation: Eugene. For the uninitiated, Eugene is that wide-eyed, innocent character who looks like he just materialised in the world ten minutes ago and is still figuring out the rules (and nervously figuring out how to ask the barista for the bathroom code).

An unexpected moment came when Asher produced an actual cardboard cutout of Eugene—because of course he has one within arm’s reach. But the real insight was his theory about Eugene's existence: having come up through Chicago improv and sketch, Asher needed a creative collaborator for the inherently solo act of cartooning. Eugene became that collaborator, a subconscious way of recreating the writer's room dynamic on paper.

When a live stream viewer requested drawings of "Eugene and his dog, who looks like Eugene," the chat collectively decided the dog should also be named Eugene. Asher immediately declared this "canon." Watching creative mythology form in real time was unexpectedly moving.

The Mankoff Hair Doctrine

I recounted Bob Mankoff's bizarre but apt advice about finding your artistic voice. Mankoff stumped with an analogy about hair styling: "You decide to wear your hair that way... why is your drawing not as distinct as your hairstyle?"

At the time, I admitted, I was too dense to understand. But eventually it sank in: stop drawing what you think a New Yorker cartoon should look like, and start drawing like myself. Asher also sold his first cartoon a month after Ellis gave him similar advice:

"Don’t draw a ‘New Yorker Cartoon’, draw an Asher Perlman cartoon that could be in the New Yorker."

This feels like the kind of obvious wisdom that's only obvious after you've bashed your head against the wall for years trying to be someone else.

The Comedy Economics of Hack

Both Asher and I shared war stories about the delicate economy of comedy crowds. His Second City experience taught him that audiences of comedy people versus regular people laugh at completely different things.

The example that stuck: during the Cubs' historically bad years, any joke that simply acknowledged their terribleness would reliably kill with regular audiences, while comedy vets groaned at the predictability.

I confessed to deploying hack MC material at tourist-heavy shows, earning eye-rolls from grizzled road comics. The unspoken rules of what's permissible comedy form our intricate ecosystem—one where Ellis serves as our "encyclopedia of cartoons," helping determine what's been done before.

Digital vs. Analogue Romanticism

Both of us admitted to fetishising paper and pen while acknowledging the seductive convenience of digital tools. Asher confessed to tapping his page to try to undo lines when working on paper. I noted how the digital safety net makes me more confident but less skilled—a creative paradox worth pondering.

By some miracle, our technical discussion revealed practical wisdom: 80-pound paper works well with iPad light boxes, draw faces first to avoid redoing entire backgrounds, and always have a brutal filing system that you'll inevitably hate.

From Hackery to Substackery

Asher had just joined Substack a month ago, and his description of the platform was refreshingly honest: "It feels like what I wanted Instagram to be, but it never was." My strategy mirrored my cartooning breakthrough—stop trying to copy what successful newsletters do, write for your own people, and celebrate the unsubscribes.

The platform discussion highlighted a broader shift away from algorithmic manipulation towards intentional consumption. As Asher put it: "I prefer things that exist outside of the algorithm now because I don't like being catered to my worst instincts."

The Bell House Launch

We wrapped with excitement about Asher's book launch at Bell House, featuring Gary Gulman, temporary Eugene tattoos, and what sounds like half the New Yorker cartooning community.

Related Reading:

Asher's journey from frustrated imitator to distinctive voice serves as both a cautionary tale and an inspiration—a reminder that the path to originality runs directly through the abject horror of just being yourself.

Thanks to everyone who tuned in to the live stream!‘til next time

Your pal,

Next week: Tuesday at 12pm, I'm chasing down Kevin “KAL” Kallagher to talk to him about his 50+ years as a working cartoonist for the Economist and —until recently— The Baltimore Sun. Add it to your calendar now!

Thank you Stan!, E. Sjule, Margreet de Heer, Loitt, Michael Maslin's Ink Spill, and the nearly 500 others for tuning into my live video with Liza Donnelly yesterday! Join me for my next live video in the app next Thursday, Sept 4th at 12pm EST when I speak with political cartoonist Kevin KAL Kallaugher. You can follow his new Substack here:

Nearly 500 people tuned in yesterday for Drawing Me Anything #25, and honestly, I'm not sure if they came for the cartoons or just to watch me fumble with my drawing setup like a broken octopus. Either way, I had Liza Donnelly on—the first person I ever subscribed to on Substack, and a cartoonist who's been breaking barriers since before breaking barriers was trendy.

From Watergate Kid to New Yorker Pioneer

Liza grew up in Washington D.C. during Watergate, which explains a lot about her political sensibilities. She wanted to be Herblock—the political cartoonist's political cartoonist—but felt like she couldn't find her voice in that arena.

"I looked at the political cartoonists that I admired, Gary Trudeau and Herblock. I just didn't feel like I could fit in. I didn't think that I had a strong enough opinion about things, which was not true, but I couldn't find my opinions, I guess. I was afraid to share them."

So she turned to the New Yorker, which she initially thought was "stodgy" until she realised it was actually full of "subtle but subversive" cartoons. This led to her becoming one of the first women to regularly publish cartoons in the magazine since after the period in the 1920s. She came up alongside Roz Chast and a few others.

The old system was beautifully archaic: Tuesdays for the seasoned cartoonists, Wednesdays for the "young upstarts" like Liza, Roz, Jack Ziegler, Mick Stevens, Bob Mankoff, and Sam Gross. After submissions, they'd go to lunch at places like The Quiet Man (an Irish bar) or The Century, sometimes hit a Mets game, and occasionally go down to Tin Pan Alley to shoot pool.

"Before we went to lunch, we would go to the other magazines, take your little envelopes of your rejects from the New Yorker, and you'd go to other places," she explained. The rejection tour included National Lampoon (where she sold her first cartoon), Good Housekeeping, Cosmopolitan—places that actually paid cartoonists, unlike today's one-shop reality.

The Live Drawing Revolution

Liza's been doing live drawing on streaming since way before it was cool. She started during the 2016 State of the Union, using an iPad with Paper 53 and one of those chunky styluses that Apple doesn't make anymore (she had to stockpile them like they were cartoon gold).

"I drew these quick drawings of what I was watching and put them on Twitter immediately because the app connects to Twitter. And nothing was like that yet on that platform at all, really. So it took off, and that's when my live drawing career sort of happened."

This led to everything from drawing the Oscars red carpet to being the first cartoonist credentialed for that gig, to courthouse sketching during Trump trials (where electronics weren't allowed, forcing her back to paper and pen like some kind of analogue warrior).

The CBS Morning Show Years and the Implosion

For about four years, Liza worked for CBS This Morning, live drawing guests and hosts, connecting their social media with the actual broadcast. They sent her to the White House, the DNC, debates—until CBS imploded with the Les Moonves and Charlie Rose scandals.

"CBS imploded, you know, Les Moonves and Charlie Rose and all that sort of—CBS imploded. And I was no longer," she said, with the casual tone of someone who's watched media empires crumble before breakfast.

"Women Laughing" Documentary

The big news is Liza's documentary "Women Laughing," which is finished and premiering in New York this fall. The New Yorker will publish it on their site, and Katie Couric (who once commissioned me to draw a deliberately bad caricature of Larry David for Sardi's) is executive producer.

The documentary features drawing sessions with contemporary women cartoonists at the Society of Illustrators, because, as Liza noted, "cartoonists are relaxed when they're drawing." It's a 35-minute short that traces the arc from the magazine's early women cartoonists through today, when about half the contributors identify as female or non-binary.

"We talked and drew at the same time because it's something that I've done with my children. And I know it's a way people are relaxed, at least cartoonists are relaxed when they're drawing," she explained.

The Rejection Game and Reinvention

We talked about The New Yorker's brutal rejection rate—drawing eight to ten ideas a week, maybe selling one if you're lucky. It's almost masochistic, but as Liza pointed out, "without that rejection, the ability to tolerate rejection, you're not going to really last long in cartooning."

"You and I, we have to really start reinventing ourselves because there's no... Magazines are dying, are almost dead, and there are no outlets for what we do, really, much. So that's why we do the live drawing, that's why we do the Substacks."

The Competition Problem

The conversation took an interesting turn when we discussed how editorial cartoonists are now competing with everyone from late-night TV shows to memes. Jon Stewart's Daily Show was one of the first to clip segments and put them online as short, opinionated, humorous pieces.

"I thought, well, that's, that's like, they're taking our job, but with video," Liza observed. "We've been in competition with memes, you know, also memes and clips of comedians doing what we do."

But there's something cartoons can do that video can't: work without language barriers, distil complex ideas into simple images, and translate across cultures in ways that English-language comedy can't.

Freedom Fighters vs. Court Jesters

I mentioned attending the RIDEP cartooning conference in France with political cartoonists from around the world—people from Tunisia, China, Sudan who had been exiled for their work.

"I kept thinking, I was talking to the American and British people... and I was saying, you know, I feel like we're so lucky, you know, we're court jesters, it feels like, whereas these people feel like freedom fighters."

It hits differently now, especially considering the current political climate and the increasing pressure on editorial cartoonists in the US.

The Herblock Story

The session ended with Liza sharing her story of meeting Herblock—her childhood hero—at a gallery opening of New Yorker cartoons in Washington in the early 80s. He came to support the younger cartoonists, pointed to her first published cartoon (a dog cartoon), and said he liked the simplicity.

"I was so scared," she admitted. Which is perfect, because meeting your heroes should be terrifying. It means they still matter.

The Three-Eyed Alien Asking a Pig for the Time

Dan McConnell in the chat requested "a three-eyed alien asking a pig for the time," which sounds apolitical until you remember that everything can be political if you squint hard enough. Or if you're drawing pigs, which, as someone pointed out, could be very Orwellian.

"Everything can be political if you think about it," Liza said, while drawing in seven lines what I couldn’t draw in seventy. I drew what was supposed to be a friendly alien, but looked more like it had strong opinions about municipal parking regulations.

The Technical Stuff

For the gear nerds: Liza uses a thick mechanical pencil (she forgot the brand), Hunt 107 nibs, and various dip pens. I'm still wrestling with my Blackwing pencils, trying to make live drawing look less like performance art and more like actual cartooning. I’m using the Hunt 101 Imperial dip pen nib.

What's Next

You can find more about the documentary at womenlaughingfilm.com and follow @womenlaughingfilm on Instagram. They're still raising money for publicity and marketing, because finishing a documentary is only half the battle.

Liza's Substack, "Seeing Things," is great reading for anyone interested in how cartoons can cut through political noise with humour. She posts daily, which is both admirable and slightly terrifying.

Next Thursday at 12 PM, Kevin KAL Kallaugher joins us for DMA #26. Kal's got this ability to distil complex political ideas into powerful images without captions, and he draws with traditional tools on a proper wooden drafting board like a civilised human being.

If you missed the live session, you can catch the replay above by becoming a paid subscriber.

I spent an hour yesterday drawing with Samantha Dion Baker —artist, author, and one the best Substackers on drawing—and came away feeling like I'd just had the best kind of therapy session. Which, as it turns out, is exactly what Sam's work is all about.

Sam joined me from her studio in Dumbo, and what started as a casual chat about pickleball evolved into a masterclass on using art as a tool for presence, sense memory, and genuine human connection. It’s crazy I get to speak to people like this every week (it’s even crazier that they speak back.)

The Accidental Artist

Sam's artistic journey is one of those creative pivots that make you believe in second acts. She spent years as a graphic designer (same!), creating pristine designs—all clean typography and careful spacing. Then life happened: kids arrived, screens became suffocating, and she found herself reaching for a sketchbook just to remember things.

"I was drawing things so well or comfortable drawing things," she told me, flipping through pages of her early work. "I was just doodling like letters and arranging things. It was very designy."

But here's the thing about doodling when you're not trying to be an artist: it becomes honest. Sam started documenting daily moments—not because she planned to publish them, but because drawing made her more present. The practice was meditative, almost inadvertent therapy.

When she published her first collection, Draw Your Day, Amazon classified it in the art therapy section. "I didn't really think about it when I was writing it," she said, "but I was like, oh, yeah. That makes sense."

The Art of Paying Attention

What I love about Sam's approach is how unforced it feels. She's not precious about her sketchbooks—they're repositories for whatever catches her attention, regardless of artistic merit. We talked about the tyranny of the "perfect sketchbook," those Instagram accounts full of museum-quality watercolours masquerading as casual sketches.

"I'm not happy with 90% of my pages”, she admitted. But that's the point. The sketchbook isn't a performance; it's a practice.

Her upcoming book, Draw Your Adventures (out July 15th—pre-order it now!), explores this idea of documentation versus decoration. It's not about capturing the Sistine Chapel; it's about noticing the "Call Your Mum" mural near your son's new apartment, or the woman across from you on the bus.

"Sometimes it's completely unrelated," Sam explained, "but it will still bring you back if you're present and you're taking it in."

The Technical Bits (For the Process Junkies)

Mid-conversation, we naturally gravitated toward tools—because what are two artists without strong opinions about pencils? Sam's a devotee of Blackwing pencils and has worked with them for years (she even illustrated their iconic poster of all the limited editions). But her real secret weapon is Derwent Inktense paints.

"I always describe them as like a cross between acrylic wash because they dry flat and watercolour," she said, layering colours on a portrait of her friend's dog, Wayne. "They're more forgiving than watercolour." (Watch the video above to see her drawing Wayne!)

I confessed my own tool obsession whilst wielding a Wren fountain pen I'd discovered the night before at a comedy show (thanks Lauren Layne and Anthony LeDonne). We compared notes on everything from mechanical pencils (neither of us likes them) to date stamps (both obsessed) to that magical Faber-Castell 14B pencil that somehow exists despite breaking all the rules of graphite grading.

(This is probably where I should mention that Sam's giving away 50 copies of her book at her launch party on July 15th in Dumbo. RSVP required—don't just show up like you're crashing a wedding.)

The Interrupted Artist

One of the most honest parts of our conversation was when Sam talked about working around constant interruptions. Her artistic practice developed not in some pristine studio, but in the margins of motherhood—quick sketches between playground emergencies, continuous line drawings because she might have to stop mid-pencil stroke.

"I was constantly being interrupted," she said. "So my process, I've learned to work in stages."

This resonated deeply. How I often wait for the "perfect" time to create—the uninterrupted afternoon, the ideal lighting, the moment when inspiration strikes like lightning? Sam's work is proof that creativity thrives on constraint, that the most meaningful art often happens in the spaces between other obligations.

Adventure as a State of Mind

As we wrapped up (Wayne the Cairn Terrier now immortalised in both our sketchbooks), Sam explained the philosophy behind her new book. Adventure isn't necessarily about passport stamps or mountain peaks—it's about approaching the world with the curiosity of someone who might want to draw it.

When you're carrying a sketchbook, you notice differently. You see the baroque curve of a fire escape, the precise way someone holds their coffee, the particular quality of light filtering through a bodega window. The tool changes the observation, which changes the experience, which changes the memory.

"It's choosing the choices of what to draw when you're on an adventure," she said. Whether that adventure is crossing Brooklyn on a bus or crossing continents on a plane.

Sam's book launches in two weeks, and honestly, it arrives at exactly the right moment. Summer in New York means everyone's moving, travelling, or at least pretending they have plans more interesting than sitting in air conditioning. But as Sam's work reminds us, the most profound adventures often happen within walking distance of home.

Just bring a pencil.

‘til next time

Your pal

Pre-order Draw Your Adventures here. Pre-orders genuinely matter for authors—they determine everything from print runs to bookstore placement. If you're planning to get a copy anyway, ordering now is the best way to support Sam and ensure the book finds its way to the people who need it.

Subscribe to Sam's Substack for a regular dose of artistic wisdom. If you're in New York, join us at her book launch on July 15th in Dumbo!

Coming soon… I'm doing something very special with Blackwing pencils and Amy Kurzweil. Can't say more yet, but it's going to be pretty epic! Stay tuned.

How Beth Spencer Started an Art Movement with a Five-Minute Sketch

I need to tell you about Beth Spencer —not because she asked me to (she didn't), but because watching her work on Substack these past few years has been like watching someone perfect the art of making strangers feel less alone with a pencil and a really good attitude about being terrible at things.

Beth runs the Introvert Drawing Club, which might be the most honest newsletter title in the history of newsletters. No grandiose promises about unlocking your creative genius in thirty days, no affiliate links to expensive art supplies that will supposedly transform your stick figures into Sistine Chapel material. Just: "Hey, you want to draw badly together? Great. Let's be bad at this thing we love."

I've been a subscriber since practically day one—her newsletter was among the first I ever signed up for when I stumbled into this Substack world with a dangerous amount of confidence in my own artistic abilities.

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What Beth does shouldn't work. In a world where everyone's selling courses and productivity hacks and systems for optimising your creative output, she's over there saying, "Actually, what if we just... drew some goats? What if we were gentle with ourselves? What if we got off our phones and made terrible art with dollar store supplies and loved every minute of it?"

The Badge That Broke the Internet

But here's the thing that makes Beth more than just another encouraging voice in the creative wilderness: she accidentally started a revolution with a five-minute sketch.

In June 2024, Beth Spencer picked up an iPad and sketched a red hand jotting the words "Created with human intelligence." She was procrastinating on her actual work—a children's book illustration—and had been seeing "a lot of concerned chatter about AI among fellow artists on Instagram." So she figured she'd post this little badge to her website to make it clear that everything there came from, you know, an actual human being.

"I thought maybe two or three people would say, 'Thanks, I'll take one,' because people love free stuff, right?" Instead, what happened was this: nearly 1,200 artists, illustrators and designers have contributed their own versions of her drawing to a growing gallery of unique images. The hashtag #hibadge2024 exploded across Instagram. Fast Company featured the movement, calling it exactly what it was: a small revolution.

Artists from the US, UK, Spain, Germany, Brazil, and Colombia started recreating Beth's scrappy little sketch in their own styles—watercolour, clay sculpture, minimalist doodles, bold hand lettering. Each one a tiny act of defiance against the algorithmic tide.

The Accidental Revolutionary

What makes this story so perfectly Beth Spencer is that she never set out to be the face of artistic resistance. "I didn't intend it as anti-tech, but as pro-human," she explained in a later interview. It wasn't about burning the machines—it was about celebrating the messy, imperfect, beautifully human process of making things with your hands.

"No software has lived life the way you have," she wrote, which might be the most succinct argument for human creativity I've ever heard. While AI churns through datasets looking for patterns, we're out here stubbing our toes and falling in love and watching our pets do ridiculous things and somehow turning all of that into art.

The badge caught fire because it crystallised something artists had been feeling but couldn't quite articulate: that there's value in the struggle, in the years of patient labour, in the way your hand shakes just slightly when you're drawing something that matters to you.

Why Beth Spencer Matters (Especially to Weirdos Like Us)

I started following Beth's work long before the badge went viral, back when she was just this thoughtful voice encouraging people to make bad drawings and be okay with it. What struck me wasn't just her art—though her loose, playful style has this wonderful "I'm having fun and you can too" energy—but her approach to the whole enterprise of being creative.

In her Zoom drawing sessions (yes, she runs fantastic live drawing sessions), people ask what supplies she's using, and half the time the answer is something from Dollar Tree. "My favourite things are these," she'll say, holding up a 75-cent brush pen that she swears works better than the fancy $11 ones.

This is revolutionary stuff, people. While the rest of us are bankrupting ourselves at art supply stores, convincing ourselves we need the right tools to make good art, Beth's over there making beautiful work with discount store markers and having an absolute blast doing it.

The Goat Whisperer

Beth has this thing with goats. (So do I.) It started after what she calls a "crushing career blow"—a book deal that fell through after she'd already told everyone about it. (Anyone who's had a creative project implode knows this particular circle of hell.) Instead of wallowing, she found a community garden in Memphis with goats and started drawing them.

"They're symbols of good in the world," she told me. And watching her capture these ridiculous, stubborn, oddly expressive creatures in her sketchbooks, you start to see what she means. There's something about the way goats exist in the world—unapologetically themselves, slightly chaotic, always ready to try climbing something they probably shouldn't—that feels like a metaphor for the creative life.

The goats led to other animals, which led to a broader philosophy about drawing from life instead of photos, about getting off your phone and actually looking at the world around you. It's David Sedaris's advice about living the "head-up life" translated into artistic practice.

The Introvert's Guide to Making Art

What I love most about Beth's approach is how it flies in the face of everything we're told about building a creative practice. No morning pages. No elaborate studio setups. No complex systems for tracking progress or measuring improvement.

Instead, it's: show up, make marks, be kind to yourself about the results. Draw the goat even if the goat looks like a potato with legs. Use the cheap markers. Take breaks to watch your cat knock over the paint water. Post the terrible stuff alongside the good stuff because the terrible stuff teaches you something, too.

Her drawing challenges aren't about competition—they're about community. People sharing their wobbly self-portraits and their wrong-colored flowers and their attempts at human hands (the Everest of artistic endeavours, as any cartoonist will tell you). Each submission is a tiny victory against the voice that says you're not good enough, not qualified enough, not artist enough to make things.

The Bigger Picture

The "Created with Human Intelligence" badge became a phenomenon because it gave artists something they desperately needed: a way to claim their space in an increasingly algorithmized world. But Beth's real contribution goes deeper than any single viral moment:

She's created a corner of the internet where it's safe to be a beginner, where process matters more than product, where the goal isn't perfection but connection. Her Substack feels like having a conversation with that friend who somehow makes you feel better about everything just by being themselves. In a time when everyone's trying to scale and optimise and hustle their creativity into submission, Beth's out there saying, "What if we just drew some animals and felt good about it?"

And somehow, that quiet revolution—one terrible drawing at a time—might be exactly what we need.

If this made you want to pick up a pencil (even a Dollar Tree one), that's Beth Spencer's magic working exactly as intended. Check out Beth's work at Introvert Drawing Club and follow her drawing adventures @bethspencerart. Fair warning: you will end up buying art supplies you don't need and feeling optimistic about your artistic abilities. Consider yourself warned.

Forward this to that friend who still thinks they "can't draw." Everyone can draw badly, and that's the point.

Thank you to those of you who tuned in to my live stream with Nishant Jain! If you missed it live, I hope you enjoy the replay above.

Join me next Tuesday & Friday for my next TWO live episodes with Best-selling Author and Artist Austin Kleon & Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes.

Tiny People, Big Ideas: My Drawing Lesson with Nishant Jain

Yesterday, I had the pleasure of talking with my friend Nishant Jain, the brilliant mind behind The SneakyArt Post, and honestly, my tiny nugget of a brain is still processing everything I saw and heard. He does this to me every time we talk. What started as me asking for help with drawing his signature "tiny people" turned into a masterclass in observation, creativity, and why sometimes the best art happens when you're trying not to be noticed.

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From Neuroscience to Sneaky Art

Nishant's journey to becoming an artist is particularly circuitous. He was halfway through a PhD in neuroscience (we’ve all be there) when he quit to become a writer, inspired by —and I love this— a particularly terrible stand-up comedian he kept seeing in Chicago. "He was awful, and he didn't get any laughs, but I would see him every night of the week. Every time I went to an open mic night, I would see him there." The persistence of this bombing comedian made Nishant realize: "What am I doing if I'm not being persistent in his way?"

Look, am I annoyed he saw me bomb so many times? No. But whatever, it led to bigger things for him. Naturally, he then quit science to write novels. (we’ve all been there) Then, almost immediately, he hit writer's block. Four times. Which led him to grab a pen and notebook and head to a café, where "sneaky art" was born out of pure frustration with words—he literally drew himself out of writer’s block.

The Philosophy of Tiny People

Here's where it gets even more interesting: Nishant's "tiny people" aren't tiny just because of scale —though they are ridiculously small. As he explained, "What makes them tiny is that they are observations of a few seconds. And as a result, they are very heavily filtered. There's just no time or scope for me to draw everything about them."

The filtering is the point. These drawings capture how we actually experience most people in our daily lives— fleeting impressions on buses, in cafés, walking past a window. "We notice heels, we notice clothes, maybe we notice somebody's hairstyle or something they said, but we don't remember everything."

Some key insights we covered:

Writing = Drawing: "Both writing and drawing are about putting together lines and shapes to give meaning to things." He breaks down faces into the letter D, ears into the letter C, and legs into half of the letter H. Suddenly, drawing feels less like some mystical skill and more like... well, writing.

Outside in, not inside out: Instead of getting caught up in facial features first, Nishant starts with the ear and works outward to capture posture and movement. "From the ear, I can go up and I can do the scalp and I can go down, and I can do the jaw." This way, even if someone moves, you've already captured what matters most.

Trust your line: This might have been the most important lesson. "When I make a long, continuous line, it has my blood pressure in it. It has my heartbeat in it. It has my nervousness in it. It is a very unique thing that only I could do in that way." Don't hedge, don't hem and haw - commit to the line.

The Miles Davis Principle

Nishant shared a quote from Miles Davis that I love, and perfectly captures the evolution from accident to intention that every artist goes through. I had this quote taped above my desk for years, so hearing someone else reference it felt like finding a kindred spirit.

"Once is a mistake. Twice is an idea. Three times is style."

On Permission & Authenticity

One of the more profound moments came when we discussed artistic permission. Nishant noted how "We think that we shouldn't need permission, but that's why we have other people in our world— we need permission from each other to live our lives." Every time an artist shares their work, they're potentially giving someone else permission to try.

This connects to his broader point about artistic authenticity: "Art is just human expression, and everybody should be doing it. But because we get hung up on it needing to look a particular way —It needs to look so good or it's not worth it— We keep denying ourselves this beautiful thing that is accessible to all of us."

The Sneaky Art Advantage

What I love about Nishant's approach is how it solves multiple problems at once: By drawing quickly and "sneakily," you avoid the paralysis of perfectionism. By focusing on fleeting observations, you develop a more present, mindful way of moving through the world. And by working small, you build what he calls "a vocabulary or a library of good lines" without the pressure of creating masterpieces.

Plus, there's something beautifully democratic about it. You don't need an easel or perfect lighting or even conventional artistic "talent" - you just need curiosity about the people around you.

"The worst time to be an artist is the best time to be an artist."

There's something both sobering and inspiring about the quote above that he heard from a comedian friend— a reminder that creating authentic work has always been challenging, but perhaps that's exactly what makes it valuable. I guess we’ll find out in these coming years.

As someone who spent way too much time trying to draw an iguana playing golf using Nishant's techniques (thanks for the request, Hue Walker), I can now say his approach just works. It strips away the intimidation factor and gets you focused on the joy of observation itself.

If you're looking for a different way to see the world, or just want to follow along with some of the most thoughtful writing about creativity and observation, I highly recommend subscribing to The Sneaky Art Post. Nishant has a course on drawing tiny people, and his book "Make Sneaky Art" comes out in September. His work reminds us that sometimes the most profound art happens not when we're trying to impress others, but when we're simply paying attention to the world around us.

’til next time,Your Pal

Yesterday, I sat down with Matt Ruby, a comedian who's somehow managed to turn drug experimentation into art, philosophical wisdom into punchlines, and crowdwork critique into a manifesto. What started as a chat about joke writing quickly devolved into an exploration of why we're all slaves to Chinese algorithms, how meditation is the antidote to everything, and why tension might just be comedy's secret weapon.

Matt's an inventive comic. He once did a special called Substance where he performs the same material drunk, high, on mushrooms, and sober – not because he's reckless, but because he's genuinely curious about consciousness. His Substack, Funny How: Letters to a Young Comedian reads as if Marcus Aurelius decided to become a stand-up comic, and his latest special Bolo proves he's not just thinking about comedy deeply – he's executing it at the highest level in the trenches of NYC comedy clubs.

The Worst Sin You Can Commit

"I think the worst sin that you can do is to be dull," Matt told me early in our conversation. "Just don't be boring." It's a philosophy that extends beyond the stage into his entire approach to art and life. When everyone else is zigging, he’s looking for what he can break to make his comedy zag. Or zog. Or something.

This isn't contrarianism for its own sake – it's strategic differentiation based on supply and demand. "If there's something that everyone else is saying, it's probably not going to be great fodder for stand-up." The result of doing the opposite is comedy that feels like watching someone dig a hole for themselves just to see if they can climb out. As Matt puts it, "Sometimes digging a hole for yourself... if you can get out of it, it's almost like a magic trick element to it."

The Philosophy of Getting Uncomfortable

Matt's approach to tension might be the most illuminating thing about his comedy philosophy. When I mentioned how audiences sometimes seize up at the topic of a joke rather than waiting for the target, he lit up: "To me, that's a golden opportunity. Tension is opportunity."

His analogy is perfect: "Tension to a comedian is what waves are to a surfer." You don't paddle away from waves – you learn to ride them. "Laughter is tension released, so if you've got them feeling tense, that's not necessarily something to run away from."

This isn't just theory. Matt's 2020 special tackled cancel culture not by taking cheap shots, but by genuinely exploring the discomfort around what we can and can't say. The audience doesn't know where he's going, which creates that crucial tension that great comedy requires.

The Substance Experiment: Malcolm Gladwell Meets Morgan Spurlock

Matt's most audacious project remains Substance, where he performed stand-up under the influence of alcohol, weed, mushrooms, and completely sober. As his friend Gina noted, "It makes sense because you have your 10,000 hours in all of those things."

The results were revelatory. Alcohol, he discovered, is "the worst possible drug there is" for performing. "I felt like I had broken a contract with the audience... as soon as the audience hears you slur, all bets are off."

The drunk set was all ego: "I'm doing great, they love this." The mushroom set was complete ego loss: "This is about us, what can we do together?" One drug builds walls, the other tears them down – a perfect window into what these substances actually do to human consciousness.

The Chris Rock Rule and the Death of The Hang

One of the most practical pieces of advice Matt shared came from Chris Rock: "If there's anything that you've talked about three times in your life with someone else, try talking about it on stage." The logic is bulletproof – if you've brought it up three times, you clearly care about it, and that authentic investment is what audiences crave.

But here's the problem: The Hang is disappearing. Matt came up in the era of Rififi, "this video store that had a bar," where comedians would stick around after shows and actually talk to each other. "After the show, everyone would just hang out and there'd be like this great hang of comedians who were on the show, newer comedians, people who just wanted to be in the scene."

Now? "Everyone's just sort of in their silos. Even when you go to a comedy show, people do their spot and then they leave afterwards." The green room that used to be full of ball-busting and zinging is now just "comics huddled over their phones."

This matters because Matt's best material comes from real conversations: "A lot of my favourite jokes or ideas for jokes don't come from sitting down at a laptop... It comes from having conversations with cool, interesting, smart, funny people." When a joke originates from genuine conversation, "the audience can perceive on stage... that's who you really are."

Meditation, Mushrooms, & the Pursuit of Presence

Matt's been meditating since childhood – his mom had a meditation room. His joke: "The first time I ever smoked weed, I was like, wow, this smells a lot like my mom's meditation room."

But his approach to mindfulness goes deeper than nostalgia. He sees meditation as "the antidote to being online and on screens all the time." We've eliminated daydreaming because we have "this IV drip of content available to us at all times," and meditation might be the only way to access that generative, wandering state our brains need.

The connection to comedy is profound. Both meditation and the Chris Rock rule operate on the same principle: "What keeps arising?" In meditation, you notice what thoughts keep coming up. In comedy, you notice what topics you keep returning to. Both are revealing something essential about who you really are.

The Crowdwork Apocalypse

Matt has thoughts about the algorithmic dominance of crowd work clips, and they're not pleasant. "It's weird to me that it did pivot into being like a dominant version of the art craft... as perceived online by people who just see it on social media."

The problem isn't crowdwork itself – it's that the algorithm loves it because it provides instant context and the voyeuristic thrill of strangers interacting. "So many people online are just alone and on a screen all day. And it is like, Oh my God, look, look at these two people who don't know each other interacting."

But here's our real shared grievance: "We're all just being slaves to the algorithms and I feel not great about having my entire art form pivot because it's what helps out Mark Zuckerberg and the Chinese government. I don't want those people determining what makes good art."

His solution? "Burn it away. Burn it" regarding material protection. "Most of the world's never even going to see it in the first place. So spread it out there. Put it out again."

The Loud-Soft-Loud Dynamic

Matt's musical background in Chicago rock informed more than just his rhythm – it gave him a framework for understanding comedy dynamics. "I love Led Zeppelin or the Pixies or that sort of loud, soft, loud dynamic and how one buys you the other."

In comedy, this translates to using silly material to buy bandwidth for deeper content. "Being silly and dumb can buy you being deep and melancholy." You can see this in Louis C.K.'s work, where "you might have something like the deepest philosophical bits and then you're gonna have like a fart joke."

The principle extends beyond individual sets to entire careers and even political discourse. "Maybe there's not one right answer. Maybe there are two poles... swinging like a pendulum instead of just trying to bully your way through like a battering ram."

Surfers, Gardeners, and Universal Wisdom

Matt's got theories about who understands the universe best, and they're surprisingly specific: surfers and gardeners. "I think surfers and gardeners sort of understand the universe in some really deep ways that the rest of us can learn from."

Gardeners understand "seasons and having a fallow period and blossoming and planting seeds and nurturing things." Surfers understand "the rhythm of the universe and waves... using the energy of the universe and enjoying when you're on the wave and also realising the wave's going to end."

Both activities force presence and acceptance of natural cycles; exactly what our screen-addicted culture has forgotten.

The Shamanic Art of Energy Management

Watching Chappelle work a small room gave Matt a revelation about comedy's deeper purpose: "I remember watching him do a set at Comedy Cellar... really feeling like, oh, this is very shamanic in how he's using the energy and playing with it."

Chappelle would push the audience away with challenging material, "making them recoil, making them be like, I don't know about this at all. And then masterfully pulling them back in via laughter." It's a push-pull technique that takes decades to master.

This connects to something profound about grief and laughter that Matt's explored: "During the process of death and grieving, how much is hilarious... because we just can't exist in that realm of tension all the time, 24 seven for weeks on end." The biggest laughs often come at funerals because "your body's craving it."

The Antidote to Everything

For Matt, live comedy represents something essential we're losing: "I get to be in a room with a room full of people who are not on their screens, who are aligned with a bunch of strangers and who are experiencing joy. And it's like, Oh, thank God... this is how we're supposed to be."

The communal experience of comedy – like going to church, AA meetings, or book clubs – offers "synchronised nervous systems" and connection to something larger than ourselves. "There's something innately that we know inside that makes us feel like the world is okay and that we're connected."

Meanwhile, screens are "pressing this button in our head where they can frack our brain stems and make us angry because it's a great way to monetise us."

Robot or Animal: Choose Your Future

Matt's vision of the future is stark but oddly hopeful: "I think there's probably some path where you choose between robot or animal in the future." You can have your Neuralink and AI girlfriend and live in virtual reality, "or you'll be an animal who has to deal with human emotions and not knowing stuff and getting lost."

His choice? "I'll choose to get lost."

The Holy Grail of Stand-Up

Throughout our conversation, Matt kept returning to what he calls "the holy grail of a good stand-up comedy joke" – material that comes from who you really are, discovered through genuine conversation and real caring. "That's who you are. You're offstage just having some drinks with a friend of yours, and it's what's coming out of you."

When material originates from this authentic place, "there's some harmony that goes on when a joke arises that way that the audience can perceive." It's not about pandering or trend-chasing – it's about finding what you actually care about and trusting that your genuine investment will translate.

(My text with a comedian today about how I accidentally ordered too many bananas resulted in them telling me ‘that’s a bit’ and then me spending this afternoon building it out into a bit I will try tonight. You should come. West Side Comedy Club, 8pm.)

The Rebellion of Presence

Despite his concerns about our algorithmic future, he maintains faith in human rebellion: "I think if people are miserable, eventually that bubbles up in a way that they're like, I don't want to do this anymore."

His work – both on stage and on Substack – feels like part of that rebellion. By examining comedy with philosophical rigour, by treating consciousness as worthy of artistic exploration, by insisting that attention and presence are the real currencies of art, he's making a case for choosing the human over the algorithmic.

In a world increasingly designed to fragment our attention and monetise our outrage, Matt Ruby is doing something quietly radical: He's asking us to sit with ourselves, notice what keeps arising, and trust that our authentic obsessions might just be the thing the world needs to hear.

And if that's not wisdom worth paying attention to, I don't know what is.

Things we talked about:

* Matt Ruby's Comedy Substack: Funny How - Deep dives into comedy philosophy and craft

* Matt Ruby's Personal Substack: The Rubes Letter - Essays on tech, mindfulness, and culture

* Working Methods - Matt's newsletter on creative process

* Matt Ruby Comedy - All his stand-up specials and tour dates

* Bolo on YouTube - His latest and best special

* Substance on YouTube - The experimental four-part series

* Mike Birbiglia's Working It Out podcast - The Ira Glass episode Matt referenced

* Waking Up App - Sam Harris's meditation app (mentioned in our chat about meditation)

* How to Change Your Mind by Michael Pollan - The psychedelics book that influenced Matt's thinking

Two Megalomaniacs Walk Into a Democracy: Ann Telnaes on Cartoons, Chaos, and Why We Can't Look Away

Earlier today, I got to speak with Ann Telnaes, 2025 Pulitzer Prize winner and one of the most fearless voices in political cartooning. (Also, one of my favourite people in the world.) We discussed the urgent question: “How do you document democracy's slow-motion car crash when two unhinged maniacs are fighting over the steering wheel?”

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Ann doesn't mince words. She never has. When I described Trump and Musk as "a petulant toddler and a drug-addled lunatic lobbing bombs," she laughed and countered with her more accurate assessment: "Male adolescents who have too many toys."

We're not dealing with political disagreements here. We're watching what happens when unlimited power meets unlimited ego, and spoiler alert: it's not that funny.

Cartoonists: The Canaries in Democracy's Coal Mine

Ann has a theory that cartoonists are "the canary in the coal mine of democracies," and honestly, after our conversation, I'm starting to think we might already have one lung full of coal dust. The documentary she's featured in, Democracy Under Siege, was made before everything currently happening actually started happening, yet it predicted pretty much everything we're watching unfold.

As Ann put it, there was urgency during Trump's first presidency, "but nobody noticed because he was so entertaining for the media to cover, because it got eyeballs." The cartoonists, however, "did a fairly good job showing who Trump was in the first one." We had a running start this time, but somehow we're still acting surprised that the leopard is eating faces.

When Free Speech Gets Complicated

Our conversation took a serious turn when we talked about Charlie Hebdo. Ann and I were both in the States when the 2015 murders happened, and like me, she felt that gut punch of "sadness and fear and fury." But here's where it gets interesting – and uncomfortable.

"At first, everybody was all... ‘Je Suis Charlie!’, Free speech! —and everybody was together," Ann recalled. "Then, all of a sudden, at least in this country, there started to be a divide." She strained friendships over defending those cartoons. So did I. "I discovered that I definitely am a free speech absolutist because I don't think you go down that path where you start talking about what you can and cannot draw or say."

Her line in the sand is crystal clear: "You're just not allowed to kill people because you disagree with them." The moment someone justifies murder with "Yeah, but the cartoons…" they've lost the argument immediately.

RELATED:

The Kitchen Counter Revolution

Here's something that blew my mind: Ann still works at her kitchen counter. This absolute legend, who's been skewering politicians for decades, is creating her masterpieces at the same place most of us eat cereal.

Her style evolved out of pure practicality. When she started, she tried to copy the McNally crosshatching approach that everyone was doing. "I realised I couldn't do those cartoons very fast. And in business, you have to work fast." So she just started doing them in her own style fast, using the brush and ink techniques from her animation background.

Sometimes the best artistic breakthroughs come from just figuring out how to pay the bills.

The Art of Evolving Evil

One thing that fascinates me about Ann's work is how her caricatures evolve. She doesn't just create one version of Dick Cheney and repeat it forever. "For me, a caricature is more about who a person is inside rather than how they look outside," she explained. "I wouldn't say that my Cheney looks like Cheney, but it certainly feels like Cheney."

This is particularly evident in her Musk cartoons. As I told her, "Your Musk evolved as he devolved." If you did a retrospective of her Musk drawings, it would show this terrifying de-evolution from celebrated businessman to... whatever the hell this is. Her recent cartoon of Musk strung out in an alley with needles around him perfectly captured not just his downfall, but the Greek tragedy of watching it happen in real time on our collective screens.

The Pat Oliphant Revelation

Ann shared an incredible story about how Pat Oliphant transformed his art. In the '60s, his style was much more cartoon-y. But when he went to speak at the Corcoran School of Art, he noticed they were teaching life drawing and decided to sit in. That's when his incredible draftsmanship really developed.

Ann's advice? "If you want to learn to draw, go take life drawing classes. I still take them." She goes to open sessions to draw the figure because "the best way to really understand foundation, to understand shapes and make your cartoon solid" is to master the fundamentals.

It's a reminder that even legends are still learning.

The Panic That Powers Creation

What drove Ann to political cartooning? Two specific moments: watching the Tiananmen Square massacre in 1989 while working on a freelance gag cartoon project, and then the Anita Hill/Clarence Thomas hearings.

The Anita Hill hearings particularly enraged her because "I was a young woman who had worked, and I had dealt with sexual harassment, and I knew all this crap that these senators were arguing about... They knew absolutely nothing about the reality of sexual harassment for women."

These moments awakened something in her: "I finally took my love of art and drawing and combined it with something, and it really clicked for me." Sometimes you need to get angry enough to find your voice.

The Mission-Driven Gender Gap

Ann has a fascinating theory about women cartoonists. There were maybe 17 or 18 working women cartoonists during the suffrage movement. "But once they got the vote, they all quit." The pattern suggests women cartoonists are driven by a mission: "We have a mission, right? We have other things, but we have to do this."

It's a different relationship to the work, less about career, more about necessity. When there's injustice to fight, women pick up their pens. When the immediate battle is won, they move on to other ways of making change.

The Real Housewives Administration

Our conversation kept coming back to the Trump-Musk fallout, and Ann captured it perfectly: "It's like watching Real Housewives except there are real-world consequences." These aren't just personality conflicts – they're affecting international relations, democracy, society, and the entire government.

The fact that two of the most powerful people on the planet are conducting their beef online makes it even more surreal. As I pointed out, "It's also performative. It's not like they're doing this in person." The online disinhibition effect is amplifying everything to a level that's "affecting our international reputation."

Why We Can't Check Out Now

Despite the exhaustion, Ann's message is clear: this isn't the time to tune out. "I had a lot of friends who just basically checked out of the news because they're tired... But I don't think now is the time to do that."

Her practical advice: "You can listen to the radio news while you're getting ready in the morning. Just keep updated on things because this administration is throwing things faster than anyone can even process them."

And then do something about it: "Call your representatives, go join a protest, make some noise because that's the only thing that's going to help us."

The Historical Echo Chamber

Our conversation got darkest when Ann talked about her German relatives and how she's always wondered how educated, normal people got "sucked into something like a Nazi government, a Hitler regime." Her conclusion is chilling: "I see it now."

"We have a guy in office right now who is definitely playing... to people's fears. Autocrats do that in order to get power and keep it." It's not hyperbole when you're watching the playbook get executed in real time.

Cartoonists’ Response to Chaos

What struck me most about talking to Ann is how cartoonists process chaos differently. We don't just report on it – we distil it, exaggerate it, make it impossible to ignore. When democracy is under siege, political cartoonists become war correspondents armed with brushes instead of cameras.

Her work during the Bush administration, particularly her devastating takedowns of Dick Cheney, remains some of the most prescient political commentary of that era. But as she noted, "now is a more frantic time with Trump and more urgent."

The question is: how do you capture the surreal when reality itself has become a cartoon?

Drawing Through the Apocalypse

As we wrapped up our chat, I was struck by Ann's combination of clear-eyed realism and stubborn optimism. Yes, we're watching democracy get stress-tested by megalomaniacs. Yes, it's terrifying. But we're also watching artists, journalists, and citizens refuse to normalise the abnormal.

Ann's still at her kitchen counter, still going to life drawing classes. She's documenting the decline while fighting against it, one cartoon at a time.

In times like these, maybe that's exactly what heroism looks like: showing up every day and drawing the truth, even when –especially when– it's too absurd to believe.

Follow Ann’s Substack below:

Thanks for tuning in!

‘til next time,Your pal,

Key Resources Discussed:

* Democracy Under Siege - The prescient documentary featuring Ann

* Columbia Journalism Review article on Pat Oliphant - Ann's piece on the legendary cartoonist's drawing process

* "Curtis Yarvin's Plot Against America" in New York Magazine - Essential reading on the neo-reactionary movement

* The New Yorker piece on Jeff Bezos and the Washington Post - Required reading on media ownership and democracy

Thank you The Bob, Brendan Leonard, Tammy Evans, Bill Cusano, Mariana Marques, and the 500 others who tuned into my live video with Austin Kleon yesterday!

New York Cartoons is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Join me for the next one on Friday at 11am EDT — I’ll be talking & drawing with special guest, Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes!

About The Guest:

Austin is the New York Times bestselling author of a trilogy of illustrated books about creativity in the digital age: Steal Like An Artist, Show Your Work!, and Keep Going.

His books have sold nearly two million copies. Two million. That's even more than the 27 of mine that sold this month! They've been translated into over 30 languages (including Australian.) New York Magazine called his work "brilliant." The Atlantic called him "one of the most interesting people on the Internet," and The New Yorker said his poems "resurrect the newspaper when everybody else is declaring it dead."

He also does talks for organizations such as Pixar, Google, Netflix, SXSW, TEDx, Dropbox, Adobe, and The Economist. This is the kind of client list that makes freelancers weep into their instant noodles.

With that intro out of the way, here is the recap of our conversation. At the bottom, I’ve also included a full list of books recommended or discussed during our one-hour talk.

Comedy Over Tragedy: What Austin Kleon Taught Me About Creative Survival

Yesterday, I had the pleasure of chatting with the brilliant mind behind Steal Like an Artist, Show Your Work, and my personal favorite, Keep Going. What started as a conversation about creative routines turned into a masterclass on attention management, the importance of play, and why treating your art like a comedy might be the secret to actually surviving as a creative person.

The Magic of Knowing What You Like

Austin started by dropping one of those deceptively simple truths: "Knowing what you like is this kind of magic tonic for your attention." It sounds almost embarrassingly basic, but as he pointed out, "we live in this world where everyone else is trying to tell you what to like constantly."

The problem? If you don't know what you actually like, "how are you going to know what you're supposed to make? Because really, what we make is more stuff like we like. We take all the things that we like and we put them together and that's our work."

This hit me hard because in previous years, I've been guilty of the exact opposite: creating things that get likes rather than things I actually like.

Austin's approach is refreshingly honest: "Only I actually know what I like, right? And so my reading life, for example, is so much richer when I just focus on what I really, really like to read."

The Brian Eno Prescription for Focus

Austin's been studying Brian Eno for over a decade, and shared Eno's current obsession with attention management. The key insight: When you truly know what you like, “you can tune in to what you're supposed to be paying attention to. It gives you focus."

This connects to something profound he observed about kids: "Kids know what they like, especially know what they don't like." They're naturally discerning in a way we somehow unlearn as adults. As Austin put it, his kids were "almost like an executive... they were very, I like that. I don’t like that—and I loved it." (He has a book coming out soon called “Don’t Call It Art” expanding on the value of this insight.

The Artist's Survival Guide

Here's where things got real. Austin shared a quote from art coach Beth Pickens that completely reframed my thinking about creative work: "Artists are people for whom their life is less when they don't work." Not that they can't do anything else, but that "my life suffers when I'm not making stuff."

The guilt around "selfish" creative time dissolves when you realize you're not just indulging yourself – you're showing up to your work, so that you can feel more alive inside, so that then you can show up for other people.

The Tragedy vs. Comedy Framework That Changes Everything

This might have been the most brilliant part of our conversation. Austin breaks down how most people think about art through the lens of tragedy: "a very special person with a gift who struggles and fights against the world... and then you know, it takes a great toll on them. So they have to shoot up heroin or whatever. And then when they get success, they get rich and they drink themselves to death."

But there's another way —the comedy approach. In comedy, you have "an ordinary person, just a regular person, maybe even a lowly person... And what they do is they bumble, they fumble, they improvise... but their fatal flaw, they don't really have a fatal flaw. What they have is their wits."

The beautiful thing about a comedy? "There is no success in a comedy. There's just failure after failure, basically. But what happens at the end of a comedy is... celebration, a wedding... People coming together at the end."

Austin's thesis: "To take a comedic approach to art and creativity is to accept yourself as an ordinary person that gets into trouble, gets in over their heads, but relies on improvisation and their wit... and play."

The Survival Mechanism of Humor

This isn't just feel-good philosophy – it's a practical survival strategy. Austin referenced Survive the Savage Sea, about a family adrift at sea for 40 days. When asked what helped them survive, the father said, "a well-developed sense of the absurd."

As Austin put it: "Comedy is not just for fun, happy times. Comedy is a survival mechanism." Mel Brooks echoes this: "If you have a sense of humor, you can get through things."

The Mathematics of Showing Up

When we talked about routine and consistency, Austin brought it down to simple math: "One day doesn't feel like much, but... if you can do one page a day, at the end of one year, you have 365 pages. That's enough for a book."

But here's the kicker —it's not just cumulative, it's exponential. Using a prickly pear cactus as an example, Austin showed how creative work compounds: "Every day isn't worth the same. If you show up every day for 365 days, the 366th day is actually going to have more power than the first day."

The Time Timer Revolution

One of the most practical tools Austin shared was his beloved timer. The paradox of creative time management: "If you want to disappear, set a timer... if you want to make time disappear, you need to work with time."

Here’s the one I have on my desk:

His process is beautifully simple: "You block off an hour tomorrow. You block it off on your calendar where no one can get to you... Then you sit down at your desk, and you set a timer for 60 minutes. Then you see what happens."

The Hobby Resistance Theory

In a fascinating tangent, Austin shared George Orwell's theory that the British "penchant for hobbies helped them resist fascism" because "people with hobbies were able to resist fascism more because they were able to spend time alone... they didn't need some sort of demagogue to tell them what to do."

His conclusion? "I think something that's happening in American culture is nobody has any hobbies anymore. And so they're just looking around for someone to tell them what to do." The solution might be as simple as more people getting into woodworking.

Finding Your Creative Comedy

What struck me most about his approach is how it removes the pressure to be a tortured genius and gives you permission to just be a regular person who makes stuff. As he said, "I think almost 99% of people shouldn't try to make their creative work their job. I think almost 100% of people should have some sort of creative practice."

The goal isn't to become the next tragic artist hero; it's to show up, play, bumble through, and maybe bring people together in the process. As he beautifully put it: "The arts have traditionally been a place for people that weren't super great at life... because they struggle with life, they give us this great art."

So maybe the secret isn't learning to suffer for your art – maybe it's learning to laugh with it instead.

I’m grateful to Austin for his time and insights— this was one of the best conversations I’ve had, and I’m lucky I got to have it.

Recommended Reading

Books mentioned in our conversation:

* Steal Like an Artist by Austin Kleon - The creativity classic that started it all

* Show Your Work by Austin Kleon - How to share your creativity and get discovered

* Keep Going by Austin Kleon - 10 ways to stay creative in good times and bad

* Newspaper Blackout by Austin Kleon - Austin's first book of found poetry

* What It Is by Lynda Barry - One of the best books on creativity ever written

* Making Comics by Lynda Barry - Essential reading for visual storytellers

* Daily Rituals by Mason Currey - How great creators structure their days

* Daily Rituals: Women at Work by Mason Currey - The essential sequel focusing on women creators

* Survive the Savage Sea by Dougal Robertson - A survival story with lessons for creative resilience

* The Comedy of Survival by Joseph Meeker - An alternative framework for thinking about creative work