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Explore every episode of the podcast 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Dive into the complete episode list for 2 Bears, 1 Cave with Tom Segura & Bert Kreischer. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.
| Title | Pub. Date | Duration | |
|---|---|---|---|
| A Tiger Almost Ate Bert's Daughter | 2 Bears, 1 Cave | 26 Oct 2026 | 00:53:57 | |
Join our next 2 Bears 5K on April 10th in Nashville, Tennessee! Register over at https://2Bears5K.com
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in from Austin and New York. Bert lays out his plan to spend 24 hours with Mark Wahlberg alongside Rob Lowe, from 3 a.m. prayer to sleeping in Wahlberg's daughter's bedroom. Then Bert says his new hour finally clicked in Philadelphia, and the guys pull up the People magazine exclusive about his couples therapy with LeeAnn that Bert doesn't remember giving. From there, Bert tries to Google a photo of himself with Dolly Parton to prove to his daughters he really met her, and instantly regrets it. The Bears also get into Bert's bench press push-up challenge, getting drunk for the first time in nine months on Por Osos, and why LeeAnn keeps asking when he'll retire. Plus: why Tim Dillon is the funniest guy alive, Bill Burr in The Social Reckoning, Tom making the case for Tom Cruise's Digger, comedy as a belly flop contest, why you never turn your back on a tiger, and Bert's plan to keep a pygmy hippo at home.
2 Bears, 1 Cave Ep. 345
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:11:07 - Bert's People Magazine Exclusive & The Dolly Parton Photo
00:17:14 - The Bench Press Push-Up Challenge
00:25:11 - Bert Got Drunk & LeeAnn Asks About Retirement
00:33:39 - Bill Burr's Social Reckoning & Why Digger Bombed
00:39:16 - Why Comedies Stopped Working & The Belly Flop Contest
00:44:57 - Never Turn Your Back On A Tiger
00:49:44 - Bert Wants A Pet Pygmy Hippo & Wrap Up
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| Shane Gillis vs SNL: Round 2 | 2 Bears, 1 Cave | 19 Oct 2026 | 01:07:22 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in with Tom in Austin and Bert in New York for the Food & Wine Festival. Tom opens by tackling the Shane Gillis backlash from his SNL monologue, while Bert tries to stay out of it for once (he just really loves those pants). The Bears react to the livestreamed execution of the Fort Hood shooter getting called off. Then Bert declares himself Team Katie for new White House press secretary Katie Zacharia, from her shaky first briefing to her gym pics and the bar exam she failed, and the guys give her three months, tops. He also opens up about his people-pleasing after a woman on a plane Googles him and asks, "What did you do?" Plus: Condoleezza Rice's 9/11 story, Bert buying Napoleon's cologne in Paris, Pope Leo's surgery, a maintenance guy catching Bert's 54-year-old mirror selfie, Bert's street-interview do-over, Chris Distefano charming Rachael Ray on Something's Burning, and Mark Zuckerberg's first Guinness.
2 Bears, 1 Cave Ep. 344
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://ccpg.org/. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in 7 days. Trade to get Predictions Dollars that expire in 1 year. $50 in rewards issued every 7 days via click to claim for 21 days. One non-withdrawable reward redeemable. Terms at https://dkng.co/audio. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.
Chapters
00:00:00 - Intro
00:00:58 - Shane Gillis' SNL Monologue
00:06:28 - Bert Stays Quiet For Once & Those Gym Pants
00:18:35 - The Fort Hood Shooter's Execution Gets Called Off
00:23:15 - Katie Zacharia & Condoleezza Rice's 9/11 Story
00:27:58 - The George Bushes & Napoleon's Cologne
00:35:03 - The Press Secretary Failed The Bar & Bert's Oval Office Plan
00:42:31 - "What Did You Do?" Bert Gets Googled On A Plan
00:48:25 - Pope Leo, Bert's Mirror Selfie, & The Street Interview Do-Over
00:56:50 - Chris Distefano Charms Rachael Ray
01:01:30 - Zuckerberg's First Guinness & Wrap Up
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| The Sebastian Maniscalco SiriusXM Drama | 2 Bears, 1 Cave | 2 Bears, 1 Cave | 12 Oct 2026 | 01:10:33 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in from the road, with Tom in Atlanta and Bert in Philly on his Permission to Party World Tour. The Bears debate whether they'll watch the Pentagon's livestreamed firing squad execution of the Fort Hood shooter, then dig into the SiriusXM Raw Dog Radio shakeup that had comics coming after Sebastian Maniscalco, and how one video turned into Bert starting a comedians union (Leanne is handling it). From there, Bert swears he'll die with his beard, finally tells Tom about the shot in Bad Thoughts season two he can't believe made the cut, and gets fired up over hood horse racing in Mississippi. Plus: Mike Ditka's one-take steakhouse commercial, Michael Jordan finding his lost championship rings in a forgotten safe, Chamillionaire's $25,000 autograph, Barry Sanders and The Fridge, and Tom getting pitched hair transplants.
2 Bears, 1 Cave Ep. 343
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:06:15 - Should You Watch The Fort Hood Shooter's Execution?
00:12:14 - Black Horse Racing & Sprinting On A Horse
00:19:31 - Bert Will Die With This Beard & The Bad Thoughts Shot
00:24:52 - SiriusXM, Raw Dog Radio, & The Sebastian Maniscalco Backlash
00:35:19 - Bert's Comedians Union
00:41:25 - Spam Calls & Mike Ditka's One-Take Commercial
00:46:34 - Michael Jordan's Lost Championship Rings
00:56:52 - Barry Sanders, The Fridge, & Elway's Two-Minute Drill
01:03:07 - Tommy Time & Wrap Up
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| The Most Delusional Man In Comedy | 2 Bears, 1 Cave | 05 Oct 2026 | 01:11:13 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer call in from opposite ends of the map: Tom on a day off from his movie in Atlanta, Bert from Cleveland's Rocket Mortgage arena. Bert pulls up old Hollywood stars next to today's to prove Tom belongs in Cocoon, and Tom fires back that Bert looks like ten pounds of shit in a five-pound bag. Then Bert drags in an arena worker to vouch for his looks, and she guesses Tom is 45. From there, the Bears lock in a bench press push-up challenge, Bert asks Claude who he should support between Israel and Palestine, before he finally admits to needing a seatbelt extender. They also get into Zach Bryan's Free Palestine shirt at Gillette Stadium, Ari Emanuel's memoir Roll the Calls, Bert's brutal gum surgery, Tom Cruise's Digger, and Tom introducing Bert to the cinematic universe of Quan Millz.
2 Bears, 1 Cave Ep. 342
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:04:09 - Football, The Metric System, & Catching Strays
00:09:13 - Tom Belongs In Cocoon
00:16:07 - One-Drink Bert & The Bench Press Push-Up Challenge
00:28:11 - Club Runs, Zach Bryan, & The Pillow Debate
00:33:20 - Goodwill Listening & The Gillette Stadium Beef
00:37:15 - Bert Asks Claude To Pick A Side
00:44:10 - "Do You Need Readers, Ma'am?"
00:46:58 - Pretty Privilege & Bert's Seatbelt Extender
00:50:31 - Ari Emanuel's Memoir & The Quan Millz Universe
00:58:24 - Animating Bert's Dreams & Tom Cruise's Digger
01:05:23 - Oppenheimer On A Phone & Wrap Up
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| Tom Cruise Pulled His Own Tooth Out w/ Rob Lowe | 2 Bears, 1 Cave | 28 Sep 2026 | 01:52:34 | |
Presale tickets for Toms new tour Preposterous go live September 30th at 10am. Make sure to get yours over at https://tomsegura.com/tour and use code: TOMMY
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Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.
If your revenues are at least in the seven figures, get our free business guide, Aligning for the Agentic Era: How AI Is Changing Everyday Work, at https://netsuite.com/BEARS .
Get started with ShipStation today and get sixty days free at https://ShipStation.com, with code cave.
This week, Tom is off somewhere, so Bert Kreischer is joined by the legendary Rob Lowe, back in the Cave to talk about his new movie The Musical, the Sundance comedy with a twist so audacious the big distributors were too scared to buy it, now playing in theaters. Rob breaks down the 18-day shoot, the moment that makes audiences gasp, and why a small theatrical run still beats a mystery streaming "hit." From there, the two get into learning stick on La Cienega, LeeAnn's endless story recaps, Tom Cruise pulling his own tooth for The Outsiders, and Paul Newman's legendary hangs. Bert opens up about his Free Bert season two meltdown and the night he forgot how to yawn, Rob shares what 36 years of sobriety taught him, and they pitch the ultimate Netflix show: 24 Hours with Rob & Bert, starring Mark Wahlberg as Dirk Diggler. Plus: Usher's house tour, Bryson DeChambeau's eagle, and the national anthem bit.
2 Bears, 1 Cave Ep. 341
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:39 - Skinny Bert & Driving Stick On La Cienega
00:10:43 - Bert Doesn't Listen & The Cousin Who Can't Eat Anything With A Hoof
00:23:54 - Tom Cruise Pulled His Own Tooth & Butch Cassidy Cool
00:32:05 - The Musical & The Twist Nobody Would Buy
00:48:40 - The Night Bert Couldn't Yawn
00:54:54 - Measured Drinking & Rob's 36 Years Sobriety
01:00:37 - Paul Newman
01:05:43 - Rob's Headshot Composites & Growing Up Before Phones
01:11:15 - Timothée Chalamet, Press Tours, & Tom Cruise's Perfect Day
01:20:22 - Mark Wahlberg's 4AM Club & Bryson DeChambeau's Eagle
01:32:11 - Stunt Flying With Tom Cruise & & The National Anthem Bit
01:41:58 - Humble Sons & Usher's Netflix House Tour
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| Raygun Deserved The Gold Medal | 2 Bears, 1 Cave | 21 Sep 2026 | 01:13:26 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are on separate sides of the country, but still together in our hearts. Tom's about to film a movie and Bert's been running his takes through ChatGPT before he says them out loud, which still doesn't stop LeeAnn and his daughters from destroying him over The Pastor's Wife. Bert explains how Last Comic Standing edited him into the villain, and how much public misrepresentation a person should take before they swing back; Michael Jackson, Shane Gillis, Johnny Depp, Joe Rogan, and Bert's "how many bees until you start swatting" theory. From there, Bert delivers the two greatest analogies of his life, Tom demands the production Bible for Tenet to understand it better, and Bert turns his garage door into a guillotine. They also get into Kyle Forgeard of Nelk Boys running seven marathons in seven days, Bert's daughters hijacking his couples therapy to tell the therapist he only feels emasculated at Lowe's, and Bert's case that Raygun should have won the gold medal and that Jackson Pollock was a shill.
2 Bears, 1 Cave Ep. 340
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit http://ccpg.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in 7 days. Trade to get Predictions Dollars that expire in 1 year. $50 in rewards issued every 7 days via click to claim for 14 days. One non-withdrawable reward redeemable. Terms at http://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.
Chapters
00:00:00 - Intro
00:00:38 - ChatGPT Approved Takes & Death Of The Pastor's Wife
00:07:17 - How Many Bees Until You Start Swatting? + Purple Doritos
00:15:02 - Tom's Movie Beard & Revisiting Tenet
00:28:44 - 365 One-Minute Episodes & Bryson DeChambeau's Hole In One
00:34:08 - Mountain Dew Sizzle
00:38:01 - Football Segue
00:39:19 - Kyle Forgeard's Seven Marathons & Andrew Schulz's Miami Era
00:43:50 - Bert's Tom Impression & Couples Therapy With The Girls
00:51:03 - The Honey Deuce & Bert's Return To Drinking
00:56:16 - What Olympic Sport Could You Actually Get Good At?
01:02:50 - Raygun Deserved The Gold & Jackson Pollock Was A Shill
01:12:15 - Wrap Up
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| What Percent Gay Are You? | 2 Bears, 1 Cave | 14 Sep 2026 | 01:12:58 | |
Check out Hoop and Huddle, YMH Studios' new comedy sports show, hosted by comedians Luke Touma & Nate Marshall. Two friends talking basketball, football, and whatever ruined their weekend. Less "analysts breaks down the tape," more "your boys yelling at the TV." https://www.youtube.com/@UCdaQbXFKAuvKcZcwieo8A6A
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Sign up and get 10% off at https://BetterHelp.com/bears.
Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.
Welcome back to the cave! Hunter Biden says he's 48% gay, which raises the only question that matters: what percent are you? Bert and Tom build the math from zero, clothes, dicks, physiques, saunas, eye patches, a $5,000 face laser, and Bert climbs a lot higher than he expected to.
Along the way: why Bert can't watch Sophie Cunningham highlights, the uncomfortable truth about loving Jason Williams, John Stockton's total lack of pizzazz, the hunt for a white DB in the NFL, Bert calling his dad mid-episode to check the family for slave owners (Tom's family does not come out clean), Bert's sister telling him to grow up about his sleep anxiety, Ila volunteering to fight Tom's ten-year-old in the Octagon, the 2:30am Dodger Stadium aftermath, a device that grades your poop, and Bert's full-throated defense of the Philadelphia Eagles' male cheerleader.
Plus: this week's Mountain Dew summer sizzle submissions, including one that requires $2.6 million of CGI and one that just shuts Bert up.
2 Bears, 1 Cave Ep. 339
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
In Partnership with DraftKings. The Crown Is Yours. Bet with DK Sportsbook: Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://ccpg.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Bet to get Bonus bets that expire in 7 days. Trade to get $50 in Predictions Dollars that expire in 1 year, issued every 7 days via click to claim for 21 days. 1 non-withdrawable reward redeemable. Predictions offer void in New York. Ends July 19th. Terms at https://dkng.co/audio.
Chapters
00:00:00 - Intro
00:00:14 - Hunter Biden Says He's 48% Gay
00:06:23 - Clip Farms, Sophie Cunningham, & Jason Williams
00:15:32 - John Stockton, White Boxers & Tim Dwight
00:29:23 - California's Slavery Bill & Bert Calls His Dad
00:34:41 - The Girlfriend, The Sister, & The Fight Challenge
00:42:34 - The Dodgers Game Aftermath & A Whoop For Your Toilet
00:46:11 - Male Cheerleaders, Female Urologists, & Checking Out Men
00:52:38 - Hiding From Lightning With A Grindr Meetup
00:59:05 - Comedian OnlyFans & Ohtani's $17 Million Translator
01:05:44 - Mountain Dew Summer Sizzle Submissions
01:11:34 - Wrap Up
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| Jelly Roll Called The President A Fat Pig | 2 Bears, 1 Cave | 07 Sep 2026 | 01:14:10 | |
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Welcome back to 2 Bears 1 Cave! This week Tom Segura and Bert Kreischer dive right in with Jelly Roll's headline-grabbing Kimmel monologue where he addressed the president as "from one fat pig to another." Bert then takes full credit for Jelly Roll's weight loss and the entire genesis of the Two Bears 5K, because technically he was in the room when that casually became a thing. They also have exciting news, a new 5K is coming in April and it's going to be bigger than ever.
From there, Bert opens up about the panic attacks he's been having, severe, physical, and rooted in something he now understands: a complete lack of childhood bedtime structure. Tom grew up getting nightly Catholic prayers, a sign of the cross from mom, and the full rosary in the car for any trip over ten minutes. Bert grew up watching Letterman alone at nine years old at 3am while his dad slept off a ten mile run. The bears compare notes on childhood bedtime routines, how they each put their own kids down now, and what sleep anxiety looks like when it hits a grown adult, including Bert's most recent 36-hour panic attack that started when a friend told him he yawns too much and he forgot how to do it. He couldn't yawn for a day and a half. He finally yawned in couples therapy. That's where we are.
They also get into Mel Gibson getting lightly canceled for mocking a sign language interpreter (on the scale of Mel Gibson incidents, this doesn't even register), a game of complimenting Salma Hayek on the one thing she's never heard in her 60 years on earth, Tom Hardy's new rap album, Jonah Hill's white belt jiu jitsu bravado and whether he'd actually beat Jason Bateman's ass, the Eddie Bravo black eye that made Bert walk out of a jiu jitsu class without ever taking his jeans off, and the Times Square Stabber whose fat padding made every taser completely ineffective and whose stabbing motion made this incident appear beyond ridiculous at first.
2 Bears, 1 Cave Ep. 338
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Canada. Bet with DraftKings Sportsbook to get Bonus bets that expire in seven days OR Trade with DraftKings Predictions to get Predictions Dollars that expire in one year. Event contract trading involves risk of loss. Predictions offer void in New York. Non-withdrawable Rewards issued as Fifty dollar click-to-claims every seven days for twenty-one days. Terms at https://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.
Chapters
00:00:00 - Intro
00:00:18 - Jelly Roll Called Trump A Fat Pig on Kimmel
00:15:49 - Mel Gibson's Sign Language Incident & Cancel Culture
00:22:32 - Childhood Bedtimes & Panic Attacks
00:33:38 - Putting Kids to Bed & Bert's Sleep Anxiety Deep Dive
00:41:44 - Bert Forgot How to Yawn and Had a 36-Hour Panic Attack
00:51:25 - Salma Hayek At 60
00:55:47 - Tom Hardy's Album, Shapeshifters & Jonah Hill's White Belt Energy
01:05:56 - The Times Square Waddling Stabber
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| Breaking Down The Barstool Brawl | 2 Bears, 1 Cave | 31 Aug 2026 | 01:46:23 | |
SPONSORS:
https://dkng.co/bears New DraftKings customers, sign up with code BEARS spend five bucks to get $200 in rewards within 21 days, includes all markets.
For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://hims.com/bears
If your revenues are at least in the seven figures, go to
https://netsuite.ai/bears.
Visit https://Betterhelp.com/BEARS.
Get started with ShipStation today and get sixty days free at https://ShipStation.com, with code cave.
Tom Segura and Bert Kreischer are back in the cave and surprise surprise, Bert opens with a confession: he wishes he'd never quit drinking. What follows is a full inventory of the modern male brain, the online pastor Tom watches every morning to get inspired, why 17-year-olds have no business being nostalgic for anything, the exact moment each of them gave up on playing pro sports, and why comedians never seem to get that same reality check. The guys break down Bert's Whoop addiction and the blood clot that started it, get talked into a completely fictional performance-enhancing stack for a 5K, fall in love with bull riding legend JB Mauney, pitch the worst sponsorship idea in podcast history, and watch a food delivery driver take on the entire Barstool office. Then it's cringe cancellation, sobriety influencers, 4:23 a.m. morning routine guys, and a long, very funny argument about which movie stars are actually men and which ones just look at themselves in the mirror. Plus Bert's new fragrance obsession, the colognes of Napoleon, Elvis and JFK, Sebastian Maniscalco's four seasonal robes, Joe Rogan's splits, Billy Bob Thornton at the CMAs, and a big announcement about the future of the show.
2 Bears, 1 Cave Ep. 337
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Bet with DK Sportsbook: Gambling Problem? Call 1-800-GAMBLER, 1-800-MYRESET. Connecticut: call 888-789-7777, visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in seven days. Trade to get Predictions Dollars that expire in one year. $50 in rewards issued every seven days via click to claim for twenty-one days. One non-withdrawable reward redeemable. Terms at https://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.
Chapters
00:00:00 - Intro
00:00:17 - The Jewish Joke Bert Can't Tell On Stage
00:04:26 - Pastor Manning
00:09:09 - Period Sex Confessions & Giving Up On Sports
00:21:50 - Nobody Quits Comedy Or Drinking
00:31:31 - Whoop Obsession, The Blood Clot, & Tren
00:37:09 - JB Mauney & The PBR
00:44:27 - Motorcycles & The 12 O'clock Boys Sponsorship
00:46:56 - The Barstool Helmet Fight
00:52:58 - Fighting Women
00:56:13 - Cringe Cancellation
01:01:35 - Tom's Pep Talk & Bert's Therapy
01:05:05 - Sobriety Influencers & Morning Routine Guys
01:09:04 - Cringey Actors vs. Real Men
01:19:33 - Bert's Fragrance Obsession
01:30:00 - Drakkar Noir Nostalgia
01:36:49 - Sebastian Maniscalco Is A Study
01:40:04 - Bert Meets Billy Bob At The CMAs
01:44:26 - 2 Bears Is Going Back To Weekly
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| Stavvy Called Us Out | 2 Bears, 1 Cave | 24 Aug 2026 | 01:25:41 | |
SPONSORS:
Look for Mountain Dew in stores near you at https://mountaindew.com
Thanks to MANSCAPED for sponsoring today’s video! Get The Beard Hedger Plus for 15% OFF + Free Shipping with code “BEARS” at https://Manscaped.com!
Start your free trial at https://SHOPIFY.COM/bears
For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://hims.com/bears for your free online visit.
This episode is sponsored by BetterHelp. Visit https://Betterhelp.com/BEARS.
Head to https://FACTORMEALS.com/bears50off and use code bears50off to get 50 percent off and 1 free breakfast item per box for 1 year, while supplies last until 10/31/2026.
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer celebrate Bert officially entering the Guinness Book of World Records for The Machine, possibly the most performed signature story in comedy history, and immediately spiral into the comedy record arms race: Shane Gillis' 77,000-person show, Nate Bargatze's 2 million tickets, the Dane Cook vs. Dave Chappelle longest-set war, and Bert's plan to lock 75,000 paid "hostages" inside Raymond James Stadium and perform for ten straight hours. Then the Bears respond to Stavros Halkias calling out comics who fly private, and explain why he's absolutely right: nobody gets funnier on a private jet. From there, Bert declares Busboys, the new Theo Von and David Spade movie, the greatest piece of art he's ever seen, and Tom finally watches The Odyssey, only for Bert to officially turn on it over the Travis Scott cameo. Plus: Gaddafi's all-female Amazonian Guard, plane-crash hypotheticals, Chimp Empire is the best reality show ever made, Mick Jagger on fame, and why the Bears are grateful they got famous late.
2 Bears, 1 Cave Ep. 336
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:18 - Comedians Getting Guinness Records
00:07:24 - The Attendance Record Arms Race
00:18:09 - Stavvy Says Private Jets Don't Make You Funnier
00:24:25 - Lunch Pail Phonies & Staying Honest
00:35:39 - Busboys Is A Secret Masterpiece
00:41:55 - Tom Finally Saw The Odyssey
01:03:45 - Por Osos At Frenchies & MacDill
01:07:29 - The Sexiest Military & Plane Crash Hypotheticals
01:12:08 - Chimp Empire
01:15:26 - Leanne's Birthday & The Black Crowes
01:20:28 - Mick Jagger On Fame
01:24:18 - Wrap Up
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| Tom & Bert's Brutally Honest Odyssey Review | 2 Bears, 1 Cave | 10 Aug 2026 | 01:01:56 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are back in the cave after eight weeks apart, and they open with a full review of The Odyssey, Lupita Nyong'o as Helen of Troy, Matt Damon's rogue Boston accent, and why Jon Bernthal is Hollywood's most legendary napper. From there, Bert unveils his billionaire rebrand (Sabah shoes, LBJ Stetsons, and the top five shoes billionaires wear this fall) before getting real about sobriety, anxiety attacks, and self-diagnosing 12 terminal illnesses in a single month. The Bears also spiral into the movies that blindsided them, Primal Fear, The Sixth Sense, Memento, Fight Club, and why the DIY hits like Obsession prove Hollywood is in another pivot moment. Plus: Project Hail Mary vs. the 15-hour audiobook, Bert's theory that this is the funniest (and most jacked) generation of comics ever, college football weight-room PRs, Jason Kelce showing up for a 9 AM bench session, and a meet & greet at MacDill Air Force Base August 14. If you missed the Bears, this one's for you.
2 Bears, 1 Cave Ep. 335
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Bet with DK Sportsbook: Gambling Problem? Call 1-800 GAMBLER, 1-800 MY RESET. Connecticut: call 888-789-7777, visit http://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in seven days. Trade to get Predictions Dollars that expire in one year. Fifty dollars in rewards issued every seven days via click to claim for fourteen days. One non-withdrawable reward redeemable. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State. Terms at http://dkng.co/offer. Limited time offer.
Chapters
00:00:00 - Intro
00:00:26 - The Bears Review The Odyssey
00:10:34 - Bears At MacDill Air Force Base
00:11:15 - Project Hail Mary & Bert's Cute Shoes
00:23:37 - Bert's Drinking Again
00:33:36 - Obsession & The New Hollywood Pivot
00:39:00 - The Best Twist Movies Ever
00:52:33 - Everyone's Got Abs
00:56:02 - College Weight Room Energy
01:00:44 - Wrap Up
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| Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave | 27 Jul 2026 | 01:03:26 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer compare their two very different eras of being fat, Tom's custom-made fat guy shirts, hard visceral fat vs. soft fat, and why losing weight made everyone think Tom got lip injections. Bert's sober documentary binge takes them from Patient Zero "Gay Tom" spreading AIDS across the Air Canada route map to Concorde pricing scams. Tom also reveals the fattest thing he's ever seen Bert do: ten appetizers, four entrées, and twenty doubles in Tallahassee. Bert also retells Bill Hader's retelling of Henry Rollins meeting David Lee Roth, and his daughter's instantly legendary Boston Tea Party take. Then things get real: a midlife crisis YouTube video sends Bert and LeeAnn into a "sell everything and get five apartments in five cities" fantasy, LeeAnn gets brutally honest about when she was happiest, and Tom breaks down the difference between happy and content. Plus: Hulk Hogan inflating Andre the Giant's weight, Julian's belt reaction to the Michael Jackson movie, Whoop resting heart rate brags, Craig Robinson's dunk, and the great first sweat vs. last sweat debate.
2 Bears, 1 Cave Ep. 334
https://tomsegura.com/tourhttps://www.bertbertbert.com/tourhttps://store.ymhstudios.com
Chapters 00:00:00 - Intro00:00:52 - Fat Tommy Vs Skinny Tom00:09:16 - Patient Zero, Polio, & The Concorde00:19:38 - The Fattest Thing Tom Ever Saw Bert Do00:23:55 - Bill Hader, David Lee Roth & Boston Tea Party00:32:21 - Hulk Hogan, Macho Man & LeeAnn Off Leash00:36:37 - Five Apartments In Five Cities00:46:12 - Bert's Midlife Crisis Theory00:54:34 - "You're Not Hitting The Notes, Mike"00:57:05 - Whoop Brags & Craig Robinson Dunking01:02:36 - Wrap Up
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| Bert Gets Bullied By Lou Reed's Ghost | 2 Bears, 1 Cave | 13 Jul 2026 | 01:14:17 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer spiral through Bert's newest crisis: figuring out which musicians would actually like him. After Lou Reed tells him off mid-treadmill (entirely inside Bert's head), Bert starts deleting Jane's Addiction and Radiohead from his library, relives Shane Gillis walking out of a Wilco concert after five seconds, and learns his most-played song of all time is "Higher" by Creed. From there, the Bears get into Tom's tour of Kid Rock's 20,000-square-foot, two-bedroom replica White House and meeting Jimmy John from Jimmy John's, a deep dive on Subway Takes and why Bert believes celebrity hot takes are all fake, the viral "white people shouldn't sit on stoops in Bed-Stuy" debate, and a deeply satisfying story of a first-class line cutter getting humbled in front of Viola Davis. Bert also opens up about the final days of his five-and-a-half-month sobriety run, including the recovery books, journaling on planes, and why his first drink back is happening at his daughter Georgia's University of Oregon graduation before going scorched earth on the dad who posted his 4-year-old breaking a rope swing "world record" in Moab. Plus: the MyPillow guy, the thumb-to-arm gut health test, Garth Brooks friendship fantasies, and why Moby would hate them both. If you missed this show, this one's for you.
2 Bears, 1 Cave Ep. 333
https://tomsegura.com/tourhttps://www.bertbertbert.com/tourhttps://store.ymhstudios.com
Chapters00:00:00 - Intro00:01:11 - Lou Reed Talks Shit to Bert on the Treadmill00:04:27 - Kurt Vile, Bob Dylan, & Shane Gillis Walking Out on Wilco00:16:15 - Deleting Every Musician Who Wouldn't Like Bert00:25:00 - Kid Rock's Replica White House & Jimmy John From Jimmy John's00:28:51 - MyPillow, Workout Underwear & Sleeping Naked00:31:11 - Subway Takes & J.Lo's Rented Hot Take00:41:01 - White People on Stoops00:43:47 - Airport Line Cutters00:50:09 - Bert's Last Week of Sobriety01:01:21 - The 4-Year-Old Moab Rope Swing Rant01:13:03 - Wrap Up
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| Tom Poops The Bucket, Bert Shit The Bed | 2 Bears, 1 Cave | 29 Jun 2026 | 01:06:48 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer dig into the wild, unexpected Black audience response to Bad Thoughts Season 2, Tom debuting his "out of your control" philosophy on how comedy lands, and a hilarious accounting of which comedians did and didn't text Bert about his new show. Bert opens up about getting nastier and setting harder boundaries in sobriety, comparing himself to the A-Rod and Rafael Nadal documentaries, and Tom reveals his ongoing health investigation that involves shitting in a bucket for a lab test. The Bears also spiral into a debate on regional diets and genetics, plan a mushroom trip with an actual shaman, get Bert's dad on the phone to discuss his own legendary history of public accidents, and revisit boys' locker room culture versus Gen Z's aversion to male nudity. Plus: a Mountain Dew summer sizzle reel callout to fans, a celebration-of-life merch drop business plan for when they die, and the most detailed bowel movement breakdown the show has ever produced.
2 Bears, 1 Cave Ep. 332
https://tomsegura.com/tourhttps://www.bertbertbert.com/tourhttps://store.ymhstudios.com
In Partnership with DraftKings. The Crown Is Yours. Bet with DK Sportsbook: Gambling Problem? Call 1-800-GAMBLER, 1-800-MY-RESET. New York: call 8778-HOPENY, text HOPENY. Connecticut: call 888-789-7777, visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Bet to get Bonus bets that expire in seven days. Trade to get fifty dollars in Predictions Dollars that expire in one year, issued every seven days via click to claim for twenty-one days. One non-withdrawable reward redeemable. Predictions offer void in New York. Ends July 19th. Terms at http://dkng.co/audio
Chapters00:00:00 - Intro00:00:14 - Bad Thoughts' Black Fanbase00:07:28 - Mountain Dew Summer00:11:31 - Healthiest Guy at the Party00:16:33 - The Subconscious Mind & Nasty Bert00:26:17 - Setting Boundaries & the A-Rod Documentary00:30:25 - Black Graduations, Bert's Identity Crisis & the Rafa Nadal Doc00:40:43 - Merch Plans for When You Die00:46:12 - Mushroom Trip & The Gut Health Investigation00:52:10 - Bert Shit Himself in His Sleep00:55:58 - Locker Room Talk01:00:33 - Breeding
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| Patrice O’Neal Destroyed Me | 2 Bears, 1 Cave | 15 Jun 2026 | 01:16:24 | |
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer celebrate Por Osos landing in Publix just in time for the 4th of July, which sends Bert into a full nostalgic spiral about pub subs, boat days, and taking his daughters into "international waters." From there, things get historical, the bears break down the story of the guy who invented the meter and got guillotined for it, which leads them down a rabbit hole of people killed for their big ideas, the French Revolution as the original cancel culture, and Martin Luther versus the Catholic Church.Then Bert tells stories about his relationship with the late Patrice O'Neal: getting destroyed at his first open mic, the Edinburgh trip where they lived together for 29 days watching Bruce Lee movies and Bert getting his feelings systematically demolished, and the moment he found out Patrice had tweeted something kind about him right before the stroke. Tom and Bert also spiral deep into funeral planning, who's required to show up, who gets a Sandler video instead of a live appearance, why Ari's funeral is going to involve hardcore Brooklyn relatives and a lot of confusion, the Andrew Schultz balloon clown apology Bert wants delivered posthumously, and whether or not to get cremated when science might figure something out. Plus: horror movies vs. comedy movies as investments, the film Obsession and its director Curry Baker, Bert's dad crashing the podcast mid-funeral conversation, the band Goose vs. the band Geese, and Mount Joy watching Passion of the Christ on the tour bus.
2 Bears, 1 Cave Ep. 331
https://tomsegura.com/tourhttps://www.bertbertbert.com/tourhttps://store.ymhstudios.com
In Partnership with DraftKings. The Crown Is Yours. Bet with DK Sportsbook: Gambling Problem? Call 1-800-GAMBLER, 1-800-MY-RESET. New York: call 8778-HOPENY, text HOPENY. Connecticut: call 888-789-7777, visit https://CCPG.org . On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Ontario. Event contract trading with DraftKings Predictions involves risk of loss. Sportsbook Bonus bets expire in seven days. $50 in Predictions Dollars issued weekly for three weeks, expire in one year. Redeem one non-withdrawable reward. Availability varies. Predictions offer void in New York. Ends June 28th. Terms at http://dkng.co/audio
Chapters00:00:00 - Intro00:02:21 - Por Osos in Publix & Florida Pub Sub Gospel00:08:45 - The Daniel Boone Documentary00:18:51 - The Guy Who Invented the Meter Got Killed for It00:24:59 - People Executed for Big Ideas00:33:46 - Patrice O'Neal Destroys Bert at His First Open Mic00:41:27 - Showtime Special, Party Bus, & Patrice's Funeral00:48:31 - Funerals Vs Celebration Of Life00:57:00 - Nick Kroll, Andrew Schultz & the Balloon Clown Apology01:04:11 - Bert's Dad Chimes In01:05:54 - Noga Erez, Goose Vs. Geese & Mount Joy01:09:02 - Curry Barker's Obsession & Horror vs. Comedy Movies01:15:10 - Wrap
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| Nick Kroll Convinced Netflix to Air Animated Animal Sex | 2 Bears, 1 Cave | 01 Jun 2026 | 01:45:14 | |
Gape your 4th eye with Kurt Metzger and Duncan Trussell's new podcast Mystery Boys and get to the bottom of what's really going on in the world: https://www.youtube.com/playlist?list=PL-i3EV1v5hLfZinN-4ZV4wmZ862wupBWF
Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse.
SPONSORS:
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off. Go to https://Babbel.com/BEARS
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This week on 2 Bears 1 Cave, Nick Kroll joins Tom and Bert to break down his new Netflix animated series Mating Season, why animation produces tighter comedy than anything shot on the fly, and the emotional formula behind Big Mouth that turned a filthy puberty show into something people actually shed real tears for. Along the way, they get into an all-timer story from a legendary comedy industry gathering featuring basically every comic you've ever loved, Tom's Charlie Murphy sushi dinner story, Bert's 50-pound weight loss and very specific relapse date, a true urban legend about Michael Landon and a javelin, a genuinely compelling movie pitch called The Quad Squad, and somehow end up in a deep dive on the Eichmann trial, featuring Sir Ben Kingsley showing up to a table read entirely off-book with a swastika-covered script.
2 Bears, 1 Cave Ep. 330
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:06:30 - Why Animation Forces Comedians to Actually Write
00:18:31 - The Greatest Comedy Photo You're Not In
00:25:25 - Tom's Charlie Murphy Sushi Dinner Story
00:39:33 - Raccoons, Black Voice, & Building the Mating Season Universe
00:54:46 - Did Michael Landon Kill a Man With a Javelin?
01:01:18 - A Completely Serious Movie Pitch
01:04:19 - Clothes, Bert's Transformation, & Relapse Date
01:13:07 - Nacho Figueras & the Argentina Horse Riding Disaster
01:25:13 - Gay Moose, Goats, & Nick Kroll's Full Project Lineup
01:29:54 - N.O.R.E Calls In
01:32:30 - Nick Kroll Speaks Spanish
01:36:45 - Hunting Eichmann & Sir Ben Kingsley's Unhinged Table Read
01:44:11 - Wrap
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| Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage? | 18 May 2026 | 01:12:20 | |
The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy!
Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0
Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse.
SPONSORS:
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- Get sixty days free at https://ShipStation.com with code cave
- For a limited time, our listeners get 50% off FOR LIFE, Free Shipping, AND 3 Free Gifts at Mars Men at https://Mengotomars.com
Live from the legendary Rose Bowl during Netflix Is A Joke Fest, the Bears are back and even sweatier than usual! Tom Segura and Bert Kreischer take the stage fresh off the 2 Bears 5K for a completely unhinged live episode packed with race stories, weight loss victories, comic cameos, chaos, and pure degeneracy.
Joined by Jelly Roll, Ari Shaffir, Joe DeRosa, and the guys from Are You Garbage?, the crew covers everything from losing hundreds of pounds and surviving airplane bathrooms while fat, to bidet discoveries, Netflix brunch disasters, H. Foley's iPhone nightmare, and the emotional insanity that surrounds the 2 Bears community.
Plus: Bert reveals he mailed busts of his own dick to his closest friends, Tom bombs in front of Eddie Murphy and lives to tell the tale, Ari returns from traveling the world with a surprise award, and the whole crew spirals into stories about body transformations, sobriety, addiction, and comedy fame.
2 Bears, 1 Cave Ep. 329
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:50 - Jelly Roll aka The Third Bear
00:23:40 - H. Foley & Kevin Ryan
00:49:51 - Ari Shaffir
01:03:38 - Joe DeRosa
01:12:56 - Wrap & Plugs
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| The Bears Go Up In Smoke | 2 Bears, 1 Cave | 04 May 2026 | 01:16:23 | |
The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy!
Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0
SPONSORS:
- Brought to you by BetterHelp. Sign up and get 10% off at https://betterhelp.com/bears.
- Don’t let your mind get in the way of a good time. Discover your options at https://BlueChew.com
- Get up to 60% off at https://Babbel.com/BEARS.
- Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears
- Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS. Application times may vary. Rates may vary.
- Head to https://acorns.com/bears or download the Acorns app to get started.
This week on 2 Bears, 1 Cave, Tim and Bart go up in smoke, sharing cigars together as they talk about whatever floats around in their collective heads. They talk about fat guy problems, before going into Tiger Woods' spiraling personal life. The Bears also walk down memory lane, comparing the infamous fat Bert pitching photo to one of him recently, and the drastic change is pretty staggering. They also unpack the text exchange between a student and the teacher sister of influencer Noah Beck, share some wild drug stories, and check out a clip of Doug Stanhope roasting a city council. Also the 2 Bears 5k is coming up! Hope you been training.
2 Bears, 1 Cave Ep. 328
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:56 - Fat Guy Problems
00:09:23 - Tiger Woods & Cigars
00:21:23 - Pitching Fat Pictures
00:29:30 - Noah Beck's Sister's Texts
00:43:40 - Age Differences
00:47:12 - Girl Talk
00:48:17 - Wild Drug Stories
00:59:19 - Doug Stanhope Fought City Hall
01:05:40 - Brendon Walsh Shenanigans
01:11:33 - Sabbatical & Wrap Up
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| The End Is Here w/ Ari Shaffir | 2 Bears, 1 Cave | 20 Apr 2026 | 01:12:10 | |
The End is Ari's new storytelling show! And it's finally here! Only at https://theend.ymhstudios.com/ . Get 7 full, hour long episodes of completely unfiltered stories for $29.99. Get it now!
SPONSORS:
- Go to https://ShipStation.com and use code cave for sixty days for free!
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- Text BEARS to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.
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- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
Welcome back to 2 Bears 1 Cave! This week, Tom Segura and Bert Kreischer are joined by the always unpredictable Ari Shaffir, dropping in to promote “The End”, a bold, no-holds-barred storytelling series that serves as a spiritual sequel and final evolution of his cult-favorite show This Is Not Happening.This episode dives deep into Ari’s return to long-form storytelling, breaking down how The End was independently produced with a stacked lineup featuring top-tier comics and a unique profit-sharing model that actually pays performers. The trio reflects on the evolution of comedy since Ari's original show, from Comedy Central’s heyday to today’s creator-driven landscape. The conversation spirals into outrageous personal stories, behind-the-scenes industry insights, and hilarious debates about everything from sobriety culture to the lost art of live storytelling. There’s also an unforgettable deep dive into a near-collaboration with Tracy Morgan, a story that almost made it into final show, and the unhinged unseriousness of morning show promotional interviews. Check out The End, y'all! We legit worked hard on it here at Studio Jeans.
2 Bears, 1 Cave Ep. 327
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:37 - The End
00:04:13 - Big Dicks & Big Chicks
00:12:20 - The Missing Tracy Morgan Story
00:31:10 - Morning Show Chaos
00:43:47 - 2 Bears 5K
00:47:30 - Booze Tales & Sobriety Influencers
01:01:09 - Road Trip Stories
01:08:31 - Tito's Vodka & Final Thoughts
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| Somethings Burning And It's Bert's Bus | 2 Bears, 1 Cave | 06 Apr 2026 | 01:15:01 | |
The End is Ari's new storytelling show! It's almost here! Premieres April 16 on https://theend.ymhstudios.com/ . Presale pricing only available for a short time! You get 7 full, hour long episodes of completely unfiltered stories for $24.99. Afterwards, the price will increase so get it now!
SPONSORS:
- Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS . Application times may vary. Rates may vary.
- Get 10% off your first month of BlueChew Gold with code BEARS. https://bluechew.com
- Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears
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- Get up to 60% off at https://Babbel.com/BEARS.
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Bert Kreischer and Tom Segura are back with a wild new episode of 2 Bears, 1 Cave, and this one has everything: a terrifying tour bus fire, Bert’s ongoing recovery from blood clots, near-death anxiety, celebrity gossip, and a heated defense of napping. Bert breaks down the shocking story of how his bus blew a tire outside Fargo, was left behind overnight, and then burst into flames just hours later — a moment that may have saved everyone on board. He and Tom unpack how close the situation really was, what Bert lost in the fire, and why he’s still obsessing over the hats.
The Bears also dive into Bert’s fear of flying, life on blood thinners, what it means to face mortality without booze, and the bizarre mental spiral that comes with multiple near-death experiences in a matter of months. From there, the conversation takes its usual chaotic turn into Club Shay Shay, the “lost everything and got it back” misunderstanding, the Jeffrey Epstein email chatter, Chappell Roan backlash, and whether Jon Bernthal is dead wrong about naps.
They also talk about the upcoming 2 Bears 5K in Pasadena on May 9, Bert’s current fitness goals, and whether he can break 30 minutes in the race.
2 Bears, 1 Cave Ep. 326
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Chapters
00:00:00 - Intro
00:01:20 - Bert's Bus Burned Down
00:14:47 - Losing Everything
00:18:19 - A Really Cool Gift
00:20:40 - Death Is A Cruel Mistress
00:34:34 - Air Canada Accident + Other Aviation Disasters
00:43:10 - Chappell Roan
00:50:28 - Beefing With Jon Bernthal About Naps
00:56:34 - 2 Bears 5K
01:00:20 - New Bus & Doing Stand-Up Again
01:07:33 - Epstein, Fluffy, & KREISCHER
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| The Most Redacted Episode Ever | 2 Bears, 1 Cave | 16 Mar 2026 | 01:17:05 | |
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In this episode of 2 Bears, 1 Cave, Bert Kreischer and Tom Segura cover everything from Bert’s sorta sober lifestyle, weight loss, sleep improvement, and 5K training to marriage non-negotiables, separate bedrooms, and life on tour. The Bears also react to internet beef between Quentin Tarantino and Rosanna Arquette, joke about the Epstein files, discuss "kept women", talk Trump and Mar-a-Lago, share a tense aborted plane landing story, and spiral into one of their darkest and funniest hypothetical conversations yet. If you missed this show, this one's for you.
2 Bears, 1 Cave Ep. 325
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Chapters
00:00:00 - Intro
00:01:19 - Bert's Weight Loss Journey
00:07:14 - Tarantino Beef & Unbothered Rogan
00:18:31 - Chef Drama
00:22:51 - Non-Negotiables
00:33:05 - Kept Women, Money, and Wild Relationship Logic
00:39:57 - Bert Learns He's In The Epstein Files
00:43:47 - Trump & Mar-A-Lago
00:50:07 - Dahmer & Plane Crashes
00:54:59 - How Would You Prefer To Die
01:02:23 - What Language Would You Prefer To Be Killed By?
01:06:55 - Racist Thing A Black Guy Told Me
01:11:40 - Vince Vaughan On The Pod?
01:13:35 - Wrap up
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| Bert's Not Dead | 2 Bears, 1 Cave | 09 Feb 2026 | 01:02:29 | |
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This week on Two Bears, One Cave, Tom Segura and Bert Kreischer spiral gloriously through brand loyalty, fast-food hot takes, donuts, Super Bowl commercials, health scares, and the kind of brutally honest conversations only best friends can have.
The Bears break down why Pepsi Zero Sugar might actually be better than Coke Zero, debate McDonald’s fries vs. literally everyone else, and revisit classic brand wars like Burger King vs. McDonald’s and Dunkin’ vs. Krispy Kreme. From Blooming Onion horror stories to why you should never order seafood at a steakhouse, this episode is packed with food takes that will absolutely start arguments.
Bert also opens up about his recent blood clot scare, panic attacks, medications, and how the experience completely shifted his perspective on health, mortality, and gratitude. The guys also talk sleep apnea machines, Benadryl addictions, Mounjaro side effects, testosterone confusion, and why medical advice somehow never agrees ever.
Plus: donut shop conspiracies in Los Angeles, Cambodian vs. Vietnamese sandwich excellence, Krispy Kreme’s wild history, Instagram’s “fatties eating” algorithm, tracking down Ari Shaffir in the jungle, and why the 2 Bears 5K might literally save lives.
2 Bears, 1 Cave Ep. 324
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:06 - Brand Wars
00:07:07 - Weight Loss Drugs
00:14:58 - Pepsi Challenge
00:22:40 - I Bought A Donut Shop
00:39:22 - Coin Pusher
00:40:54 - 2 Bears 5K Is Back!
00:45:13 - Bert's Blood Clot
00:49:38 - Where In The World Is Ari Shaffir?
00:54:39 - Black Appreciation
01:00:41 - Wrap Up
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| The End Of Humanity | 2 Bears, 1 Cave | 12 Jan 2026 | 01:03:03 | |
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The OG Bears are back on this absolutely unhinged episode of 2 Bears, 1 Cave! Bert Kreischer and Tom Segura dive headfirst into VR porn disasters, accidental virtual orgies, and the terrifying realization that Oculus might actually be ending humanity.
Bert recounts a weekend alone that spirals into nine virtual orgies, soul-stealing eye contact, and panic-induced controller fumbling in a pitch-black room. The Bears also unpack loneliness, online hate comments, incel psychology, and how social media gives angry dudes a place to scream just to feel noticed.
From there, things somehow get deeper: wealth guilt, excess consumption, purging hundreds of shoes and jackets, Mounjaro weight loss, beating Jelly Roll in the next 2 Bears 5K, parenting chaos, friendship evolution, Jake Paul as a “god,” and why success is always part luck. Enjoy the Bears while they're here.
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2 Bears, 1 Cave Ep. 323
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https://store.ymhstudios.com
Gambling Problem? Call 1-800-GAMBLER. New York: call 8778- HOPENY or text HOPENY. Connecticut: call 888-789-7777 or visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Wager tax pass-through may apply in Illinois. Twenty one plus in most states. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://DKNG.co/audio Limited time offer.
Chapters
00:00:00 - Intro
00:00:14 - Bert's First Threesome
00:05:58 - Mean Comments
00:13:05 - Hanging With The Kids During Christmas
00:30:02 - Stroke Of Luck
00:34:11 - Excess & Purging Stuff
00:44:05 - Weight Loss, Mounjaro & Jelly Roll
00:55:15 - Jake Paul Is A God?
01:01:01 - Wrap Up
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| New Year New Roast | 2 Bears, 1 Cave | 05 Jan 2026 | 01:07:42 | |
SPONSORS:
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It’s the final Winter Bears of the season, and Stavros & Chris are ringing in the New Year the only way they know how: complaining about first class, overeating pastries, and making terrible life decisions! As 2025 wraps, the boys reflect on blown resolutions, chaotic travel plans, New Jersey “vacations,” and Chris’ catastrophic decision to roast the entire Jersey Shore cast. Plus: Delta lounge politics, childhood SNL trauma, double-the-bread-double-the-head, and Stav helping Chris talk through the worst career choice he’s ever made.
Grab a croissant, buckle up, and celebrate the end of the Winter Bears era as we begin a new year!
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2 Bears, 1 Cave Ep. 321
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Gambling problem? Call one eight hundred Gambler. In New York, call 8778-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call 888-789-7777 or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://DKNG.co/audio. Limited time offer.
Chapters
00:00:00 - Intro
00:01:09 - First Class Complaints & Latent Homo Things
00:09:00 - New Years Resolutions
00:18:27 - Roasting The Jersey Shore Cast
00:28:45 - Workshopping Roast Jokes
00:39:43 - This Is Probably A Dumb Idea
00:45:02 - The Jersey Shore Photo Roast Session
00:51:31 - New Years Plans & NFL Roasts
00:55:00 - More "Fan" Questions
01:03:37 - Final Thoughts
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| Pimping Podcast Producers | 2 Bears, 1 Cave | 29 Dec 2025 | 01:06:18 | |
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The Winter Bears Stavros Halkias and Chris Distefano return for another completely unhinged takeover of 2 Bears 1 Cave. With Tom Segura and Bert Kreischer nowhere to be found, the guys openly admit they once again didn’t prepare, and then immediately spiral into bread rankings, prostate exams, STD horror stories, religion, celebrity gossip, and the most deranged podcast business ideas ever pitched.
From focaccia-based trauma, to almost doing business with Jeffrey Epstein’s brother, this episode goes fully off the rails and never checks the map again.
Hit subscribe, brace yourself, and remember: this episode exists only because someone might need it someday.
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2 Bears, 1 Cave Ep. 321
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Chapters
00:00:00 - Intro
00:01:38 - Fat Boy Pastry Shop
00:07:42 - Just The Tip
00:11:53 - Sexually Transmitted Hilarity
00:25:13 - Family
00:31:15 - Third World Fun & Legendary Funbags
00:35:13 - Pimping Podcast Producers
00:43:42 - Doing Business With An Epstein
00:54:16 - Health Corner
01:01:52 - In Conclusion
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| Chris & Stavvy Save Christmas! | 2 Bears, 1 Cave | 22 Dec 2025 | 01:09:51 | |
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Merry Winter Bears-mas! Stavros Halkias and Chris Distefano take over 2 Bears 1 Cave while Tom Segura and Bert Kreischer are away, and immediately turn it into a holiday fever dream. The Winter Bears dive into chaotic Christmas traditions, Jewish Christmas supremacy, family trauma, weight-loss delusion, wild childhood memories, and the politics of gift-giving. Along the way, they spiral into ancestry revelations, Oldboy-level revenge fantasies, questionable parenting strategies, croissant mukbangs, and an all-time debate over the perfect Christmas Chinese food order. Grab a pastry and strap in — this might be the most unhinged holiday episode in 2 Bears history.
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2 Bears, 1 Cave Ep. 320
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Chapters
00:00:00 - Intro
00:00:57 - Revenge & Christmas Plans
00:06:57 - The Germans Always Make Good Stuff
00:16:33 - Perfect Holiday Dinner Conversations
00:23:38 - Are Greeks Whites?
00:30:40 - Let's Eat Some Tommy Bunz
00:33:35 - Christmas Gifts
00:44:09 - Greek Thieves, Bribing Kids, & Daddy Stavvy
00:52:17 - Favorite Chinese Food Order
00:59:00 - Living The NYC Dream
01:02:28 - Answering Some "Fan" Questions
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| The Summer Bears Came For The Winter | 2 Bears, 1 Cave | 15 Dec 2025 | 01:10:25 | |
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Christmas CAME early! The Summer Bears are now the *Winter Bears* and they have returned to phone it in and fulfill some contractually obligated laughs. Chris Distefano and Stavros Halkias invade YMH Studios to talk awful breakfast decisions, Bert’s cruise from hell, fat-guy medicine science, Husky-induced life chaos, bombing on MTV, fighting GLP-1 drugs, Mike Tyson saving Big Pun at The Tunnel, and why both of them should never own pets, houses, or functioning digestive systems.
It’s chaotic, barely prepared, medically concerning, and absolutely perfect. Enjoy!
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2 Bears, 1 Cave Ep. 319
https://tomsegura.com/tour
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Gambling problem? Call one eight hundred Gambler. In New York, call 8778-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call 888-789-7777 or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://DKNG.co/audio. Limited time offer.
Chapters
00:00:00 - Intro
00:03:29 - Slutty Little Breakfast
00:07:14 - Podcast Polyamory
00:14:15 - Chrissy Housing Crisis
00:21:35 - Stavros Vs Fat Guy Medicine
00:31:48 - Fat Joe, Guy Code, & Graveyard Of Failed Shows
00:46:14 - Maybe The Worst Dog Ever
00:56:17 - Geopolitical Shenanigans & NYC Mayors
01:08:11 - Wrap Up
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| My Soul Will Always Be Fat | 2 Bears, 1 Cave | 08 Dec 2025 | 01:07:19 | |
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This week, Bert’s wasting away, Tom’s tucking in his shirts, and the Bears are going into hibernation for the winter. Before that good news, Bert breaks down losing 25 lbs in a month, projectile-vomiting in airport bathrooms, and Tom producing Olympic-level protein farts. Tom also talks his new pastry empire and defends his son’s obsession with suits and hair product; along the way they dive into Bert’s DEXA scan nightmare, and some chaotic CMA stories including a Steve Martin panic-meeting and Billy Bob Thornton being a king. They also discuss robe culture, aging out of podcasting, comedian fashion, the future of 2 Bears with guest hosts, tours and the 2 Bears 5K, plus they announce the return of the Summer Bears next week. Enjoy!
2 Bears, 1 Cave Ep. 318
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Chapters
00:00:00 - Intro
00:01:02 - OzemBert & Gassy Tim
00:09:17 - Fat Boy Dreams
00:19:35 - Dressing Like An Adult Is Hard
00:28:44 - Country Music Awards Chaos
00:39:57 - Robe Guys & Big Joe Pesci Energy
00:46:22 - Crisis Of Appearance
00:52:03 - Quentin Tarantino
00:55:46 - The Winter Bears, 2025 Look Back, & 2 Bears 5k
01:06:14 - Wrap Up
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| The Dark Side of Internet Fame w/ Marcus King | 2 Bears, 1 Cave | 01 Dec 2025 | 01:28:06 | |
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This week, Bert Kreischer sits down with musician Marcus King for a wild, emotional ride—naked ocean stories with Navy SEALs, cocaine confessions, microdosing mushrooms, Southern rock rankings, and why internet comments haunt grown men at 3AM. Plus: TikTok ruining music, therapy drunk, and Bert accidentally following people who hate him. Check it out!
2 Bears, 1 Cave Ep. 317
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Chapters
00:00:00 - Intro
00:01:30 - Southern Rock & Creating Your Own Lane
00:07:01 - Marcus' Process, New Album, & Otis Redding
00:14:55 - Cigars With James Earl Jones
00:17:47 - Sobriety, Microdosing, & Losing the Sparkle
00:29:52 - Loving Yourself While The Internet Hates You
00:42:43 - Ranking Southern Rock Bands
00:49:44 - TikTok Ruining Music & Comedy
00:54:55 - It's Raining Tom
00:57:00 - Authentic Relationships
01:02:23 - The Most Realest Artists Out There
01:13:49 - Back To Top Southern Rock Bands
01:20:31 - Eulogies & Final Thoughts
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| Louis C.K. on Writing His First Novel and Returning to Stage | 2 Bears, 1 Cave | 24 Nov 2025 | 01:09:00 | |
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In this powerful and surprisingly emotional episode of 2 Bears 1 Cave, Tom Segura sits down with Louis C.K. to discuss his new novel Ingram, the creative process behind writing fiction, and the brutal emotional reality of loneliness and childhood struggle. Louis explains why he quit stand-up for over a year, how stepping away from the stage changed his life, and what ultimately pulled him back into comedy.
The conversation dives deep into fear, pain, trauma, comedy philosophy, empathy, war stories, emotional burnout, and why the darkest moments in life can shape the most powerful art. Tom reveals that reading Ingram made him cry, and Louis talks about the deeply disturbing next book he’s finishing—including a scene that shocked even him while writing it.
They also explore the controversial idea of “punching down” in comedy, the ethics of humor, and why Louis believes the funniest material comes from the messy truth of being human.
2 Bears, 1 Cave Ep. 316
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Gambling problem? Call one eight hundred Gambler. In New York, call 8778-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call eight eight eight seven eight nine seven seven seven seven or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://dkng.co/audio. Limited time offer.
Chapters
00:00:00 - Intro
00:01:00 - Becoming A Novelist, Eastern Europe, & Russian Literature
00:05:12 - Quitting Stand Up & Daily Rituals
00:08:47 - Writing Ingram & Why Tom Teared Up
00:19:38 - Loneliness, Street Kids, & the Human Threshold for Empathy
00:34:27 - Trauma, War & Emotional Damage
00:39:17 - Coming Back to Stand-Up & Rebuilding Material
00:46:22 - Upsetting Audiences, Articulating Thoughts, & Punching Down
00:59:59 - Touring Burnout & The Future of Live Comedy
01:06:42 - Final Thoughts & Tom Praises Ingram
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| My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave | 17 Nov 2025 | 01:09:07 | |
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Tom Segura returns to the cave with the one-and-only Kirk Fox, comedian, actor, and possibly a future Supermax inmate, depending on how you interpret this episode. The two dive into Kirk’s accidental tennis-career-turned-acting path, his eccentric family upbringing (outdoor showers, blood-written memorials, and a grandma in a box), and his lifelong dream of becoming either an FBI profiler or a serial killer — whichever opportunity arrives first.
From Waymo self-driving cars acting like drunk Uber drivers to territorial pissings, choke etiquette, BTK, Tommy Lynn Sells, Vince Champ the stand-up sex criminal, and a full breakdown of Supermax prison life, this episode spirals into a darkly hilarious masterclass on murder, consent, and why prison might actually be relaxing if you need more sleep.
If the FBI is listening — it’s all jokes. Probably.
2 Bears, 1 Cave Ep. 315
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Chapters
00:00:00 - Intro
00:01:34 - Tennis Legend Kirk Fox
00:08:40 - Charo Looks Like Bon Jovi
00:11:20 - Kirk’s Home Life
00:17:53 - Golden Showers
00:24:46 - More Killers & AI Sex Robots
00:33:42 - Tommy Lynn Sells & Killing by Train
00:37:43 - The Next Killer in Our Friend Group
00:40:49 - Supermax Prison Fantasy
00:46:29 - My Dad Was A Serial Killer
00:52:38 - Vince Champ: The Sex Crime Comedian
00:58:21 - Kirk’s FBI Dreams & Shamelessness
01:02:22 - Kirk & Tom Check Out Vince Champ's Comedy
01:06:07 - See You In Prison
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| Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave | 10 Nov 2025 | 01:59:14 | |
Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour .
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This week, Bert sits down with the one and only Mel Robbins for a brutally honest, hilarious, and surprisingly deep conversation about anxiety, cheating, parenting, and learning how to “let them.” From wild college confessions to Mel breaking down her Let Them Theory in real time, this episode is half therapy, half comedy, and all chaos.
They cover everything — why Bert can’t stop overexplaining to strangers (and accidentally tried to kiss Nicole Kidman), how ADHD and anxiety shaped both of their lives, and why it’s so hard to stop caring what everyone thinks. Mel opens up about her own journey through debt, dysfunction, and discovery — and Bert realizes maybe, just maybe, he doesn’t have to fix everyone to be happy.
If you’ve ever felt like you’re juggling guilt, stress, and trying to please everyone — this episode will hit home and crack you up at the same time.
2 Bears, 1 Cave Ep. 314
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:46 - What's Your Drink?
00:03:50 - College Chaos & Cheating Confessions
00:13:47 - Nobody Wants To F**k Up Their Life
00:23:12 - FOMO, Stoicism, & The Let Them Theory
00:34:42 - Why We Need to Disappoint People
00:47:55 - Family Guilt & The Dinner Dilemma
00:55:08 - An Awkward Nicole Kidman Kiss & Approval Addiction
01:01:39 - ADHD, Dyslexia, & The Volcano Inside
01:10:44 - What Could Possibly Go Wrong?
01:20:01 - Bert Gets Real
01:31:05 - Wired To Change
01:36:25 - Opportunity Of A Lifetime
01:45:51 - Let Them (And Let Yourself)
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| Duncan Trussell BLOWS Bert's Mind! | 2 Bears, 1 Cave | 03 Nov 2025 | 01:18:07 | |
Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour.
SPONSORS:
- Protect your family with life insurance from Ethos. Get your free quote at https://Ethos.com/BEARS
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- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.
Bert Kreischer celebrates turning 53 the only way he knows how — by spiraling into an existential and hilarious conversation with comedian and cosmic philosopher Duncan Trussell. From tales of Bigfoot and testicular cancer to deep dives on AI, death, main character syndrome, and whether any of us are even real, this episode swings from absurd to profound faster than Bert can take his shirt off. Duncan and Bert talk about everything — mortality, digital immortality, the illusion of self, performative living, and how comedy might be the purest form of chaos magic. Along the way, they share stories about Joe Rogan, Freddy Soto, and the strange spiritual beauty of making people laugh. There’s even a surprisingly thoughtful discussion about funerals, cruises, and the philosophy of “carpe diem.” Bert also reveals the truth about his infamous cruise (yes, the vodka shortage is real), his daughter’s fandom for Duncan, and why thumbnail culture might have “ruined podcasting.” Duncan, meanwhile, breaks Bert’s brain more than once with talk of Roko’s Basilisk, reincarnation, and smiling on the way to the gallows — all while making it sound like the funniest TED Talk you’ve ever heard. If you’ve ever wondered why we laugh at tragedy, why people live like they’re being filmed, or if you might just be an AI simulation of yourself — this is the episode for you.
2 Bears, 1 Cave Ep. 313
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:43 - Death Plans & Bigfoot’s Balls
00:03:59 - AI, Immortality & Roko’s Basilisk
00:07:02 - Main Character Syndrome
00:14:54 - Comedy, Therapy & Freddie Soto
00:17:10 - Hail Satan & The Disney Adult Disaster
00:22:46 - Loving Your Fans & Bert’s Cruise of Chaos
00:33:07 - Performative Life & The Polar Plunge Moment
00:41:50 - Are You Really You? Identity, Trauma, & Thumbnail People
00:54:17 - Smiling on the Way to the Gallows
01:03:10 - Cancel Culture, Bunkers & The Human Comedy
01:09:52 - The Weird Miracle Of Being Alive
01:13:43 - Bert Ruined A Photo Op
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| The Undertaker Goes One-On-One With Tom Segura! | 2 Bears, 1 Cave | 27 Oct 2025 | 01:10:58 | |
Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour.
SPONSORS:
- Get $10 Off at BRUNT with code CAVE at https://www.bruntworkwear.com/CAVE #bruntpod
- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.
- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
This week, Tom Segura sits down with WWE legend Mark Calloway — better known to millions as The Undertaker — for one of the most fascinating and hilarious deep dives ever on 2 Bears 1 Cave. From the grind of early wrestling days to the creation of one of the most iconic characters in sports entertainment, this episode is pure gold for wrestling fans and comedy lovers alike.
The Undertaker opens up about his unlikely path from college basketball to the squared circle, the wild meeting with Vince McMahon that birthed his legendary persona, and what it was like to rise through an era dominated by Hulk Hogan and other larger-than-life characters. He and Tom trade road-war stories, comparing the life of a traveling comedian to that of a pro wrestler — the endless travel, the brutal schedule, and the weird adjustment of coming home after months on tour.
Mark also reveals behind-the-scenes secrets of WrestleMania, his all-time favorite match with Shawn Michaels, and the brutal injuries (including being set on fire… twice) that came with three decades in the ring. Plus, he shares how he stayed committed to “living the character,” why he always wore black in public, and how he evolved The Undertaker over time to keep the mystique alive. They also discuss wrestling psychology, the art of storytelling in the ring, and the freakish athleticism of stars like Brock Lesnar, Kane, and Roman Reigns. From hilarious stories about stepping on teammates during basketball drills to heartfelt reflections on the fans who grew up with him, The Deadman proves he’s every bit as thoughtful as he is intimidating.
2 Bears, 1 Cave Ep. 312
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:09 - Wrestlemania
00:06:36 - I Wanna Be A Wrestler
00:17:17 - The Birth Of The Undertaker
00:31:26 - Injuries & Finding New Roles
00:42:40 - Big Strong Guys
00:47:35 - Shawn Michaels
00:56:17 - Novices
00:59:54 - Stupid Purchases
01:03:25 - Mike Tyson
01:06:57 - Wrap Up
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| Robert DeNiro Didn't Wanna Be Friends w/ Sebastian Maniscalco | 2 Bears, 1 Cave | 20 Oct 2025 | 01:24:38 | |
TEXAS! Tom will be in Amarillo at the Amarillo Civic Center Complex on November 1st, then November 2nd in Lubbock at Buddy Holly Hall and El Paso at the Abraham Chavez Theatre on November 6th. Go get your tickets now at https://tomsegura.com/tour.
SPONSORS:
- Head to https://DRINKAG1.com/BEARS to get a FREE Welcome Kit, including a bottle of Vitamin D and free AG1 Travel Packs, when you first subscribe!
- Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS. Application times may vary. Rates may vary.
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- Sign up for a $1 per month trial period at https://shopify.com/bears.
This week on 2 Bears, 1 Cave, Bort sits down with comedy legend Sebastian Maniscalco for one of the funniest, most honest conversations yet. They dive deep into Sebastian’s new stand-up special filmed at the United Center, what it takes to stay passionate about comedy, and how fatherhood changes everything.
From crying at movies and parenting philosophies to the “arrogance of boring” and buying boats, this episode is packed with heart, humor, and classic Bert chaos. The two swap stories about old-school comedy days, meeting Jerry Seinfeld and Robert De Niro, and the truth about balancing fame, family, and fun.
Tim will return next week...promise.
2 Bears, 1 Cave Ep. 311
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:30 - Stand-Up, Sicilians, & Sensitivity
00:14:16 - Dressed To Impress
00:22:27 - Small Talk & Small Comedians
00:34:28 - Playing The Hits
00:39:30 - DeNiro & Casinos
00:46:20 - Wine, Wants, & Life Experiences
00:56:35 - Fun Dad & Discipline Dad
01:03:05 - Pete Correale
01:07:32 - Does Sebastian Do This?
01:16:06 - Married To An Artist
01:19:08 - Edit This Out! + Wrap Up
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| Why Ice Cube Stays Mad in Every Movie w/ Funny Marco | 2 Bears, 1 Cave | 13 Oct 2025 | 01:41:44 | |
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
- Upgrade your wallet today! Get 10% Off @Ridge with code CAVE at https://ridge.com/CAVE #ridgepod
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Bert Kreischer sits down with YouTuber and social media personality, Funny Marco for one of the most effortlessly hilarious and unexpectedly deep conversations on 2 Bears, 1 Cave. The two dive into everything from guessing celebrity ages and debating who the sexiest comedian is, to the weird psychology of fame, strip club etiquette, and why Ice Cube has never smiled in a movie.
Marco opens up about his viral interviews with Nicki Minaj and Orlando Brown, the surreal side of fame, and what it means to stay grounded when everyone treats you like a brand instead of a person. Bert shares behind-the-scenes stories from The Cabin and The Machine, his friendship with Katt Williams, and what it’s really like when fame takes away your freedom to “just go.”
Funny, sharp, and full of quotable moments, this episode swings from gut-busting comedy to surprisingly real talk about authenticity, anxiety, and why being “D-list famous” might be the sweet spot.
2 Bears, 1 Cave Ep. 310
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling problem? Call 1-800-GAMBLER. In New York, call 877-8-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call 888-789-7777 or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://dkng.co/audio. Limited time offer.
Chapters
00:00:00 - Intro
00:02:17 - What's My Age Again?
00:14:14 - Interviewing Celebs & Getting A Lambo From Nicki Minaj
00:20:14 - Orlando Brown & Bert's Cabin
00:29:31 - Top Black Comedy Movies
00:40:40 - Fame
00:50:20 - Strip Clubs
00:55:55 - NBA YoungBoy
01:00:25 - The Art Of Not Giving A F
01:05:00 - Animation Domination
01:08:55 - Black Phrases
01:15:25 - Lying
01:19:46 - Chappelle, Kevin Hart, IShowSpeed, & Kai Cenat
01:28:12 - The Entertainment Of Watching People's Lives
01:36:42 - Closing Thoughts
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| Tom and Bert's Favorite OF Submissions | 2 Bears, 1 Cave | 06 Oct 2025 | 01:06:01 | |
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
- As always, get your first month of BlueChew FREE Just use promo code BEARS at checkout and pay five bucks for shipping. https://bluechew.com
-Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
- Download the CFO’s Guide to AI and Machine Learning for FREE at https://NetSuite.com/BEARS.
This week, Bert and Tom dive headfirst into the weirdest brain rot rabbit holes yet — from testing out VR porn ("you can see her fillings!") to auditioning more OnlyFans submissions, one of which that includes… a unique Por Osos bottle cameo. The Bears also pitch a business idea for a grown-man “locker room,” debate how Bert's woke daughters compare to Tom's redneck sons, and discover the world’s wildest dogs and cats. Plus: Jelly Roll’s 5K transformation, Savannah cats that look like mini-lions, and Bert’s desperate plan to sneak another puppy past Leanne.
It’s sex robots, freeze porn, fat-to-fit inspiration, and pet chaos all rolled into one classic 2 Bears, 1 Cave mess.
2 Bears, 1 Cave Ep. 309
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:03:22 - Jimmy Kimmel and Tylenol
00:08:17 - New Interest
00:15:54 - What The Kids Are Into
00:27:48 - The Bears Draft A Prospect
00:38:32 - The Locker Room Experience
00:46:18 - Jelly Roll
00:52:10 - Cane Corso vs. Dogo Argentino vs. Savannah Cat
01:01:14 - Wrap Up
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| Phones Are Making You Unfunny w/ Jimmy Carr | 2 Bears, 1 Cave | 29 Sep 2025 | 01:16:07 | |
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
- Upgrade to ShipStation today to get a sixty-day free trial at https://www.shipstation.com/cave.
- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.
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- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod
This week, Tom Segura is joined by one of the greatest one-liner comedians in the world, Jimmy Carr!
Tom and Jimmy dive deep into the craft of comedy, comparing Carr's laser-focused joke construction to Bert Kreischer's chaotic storytelling. Jimmy reveals his controversial (and hilarious) take on
marijuana legalization—mandating it for people over 50—and the tragic role of "cheap dopamine" in modern life, from social media to porn. The conversation touches on global comedy culture, the
variable reward system that drives stand-up and casinos , and why the live comedy experience is 30 times funnier than watching a special alone. Jimmy Carr also gives his final, wishful prediction for how
Bert Kreischer will die. Plus: Why the 21st Century is just the 20th century on better screens, the long wait for GTA 6, Jimmy's hilarious interactions with Stephen Hawking, the importance of gratitude, and why Tom should have read the Quentin Tarantino book. Don't miss a conversation that is smart, insightful, and packed with the sharp, dark wit that only Jimmy Carr can deliver!
2 Bears, 1 Cave Ep. 308
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Chapters
00:00:00 - Intro
00:01:19 - The Mechanisms Of Reward
00:10:08 - The Spectacular Death Of Burt Kersher
00:15:51 - The Times They Are-A-Changing
00:28:51 - Weed Takes
00:37:22 - The Privilege of Pressure & Boredom
00:43:36 - Beautiful People
00:53:56 - Boinking Bert
00:59:02 - James Bond & GTA 6
01:06:11 - Quentin Tarantino
01:12:47 - Wrap Up
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| James Gunn's Superheroes Are Flawed But Funny | 2 Bears, 1 Cave | 22 Sep 2025 | 01:19:34 | |
SPONSORS:
- Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS. Application times may vary. Rates may vary.
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In this episode of 2 Bears, 1 Cave, James Gunn joins Tom Segura to talk filmmaking and the state of the entertainment industry. Gunn opens up about directing Superman, the pressures behind it, and the relief of its success. He also discusses his role as co-head of DC Studios, building a decade-long DC universe, and the bold choice to reshoot five and a half episodes of Peacemaker with a new Vigilante.
Tom and James bond over grounded storytelling, casting decisions, and the balance between comedy, superhero films, and CGI. They also touch on the return of comedies to theaters and how the industry continues to evolve.
2 Bears, 1 Cave Ep. 307
https://tomsegura.com/tour
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:45 - Peacemaker, El Tigre, & Grounded Aesthetics
00:08:24 - Big Screen Comedy
00:22:04 - Hitting The Creative Lottery With Superman
00:32:59 - The Writing Process & Juggling Big Budgets
00:41:16 - Special FX & Special Actors
00:47:57 - Batman
00:55:53 - Star Wars
01:00:12 - Guardians Of Fun
01:04:11 - Serious Filmmaking & "Ripley"
01:08:36 - Casting Highs & Lows
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| Bert Calls His Dead Grandma | 2 Bears, 1 Cave | 15 Sep 2025 | 01:06:54 | |
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- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod
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Hey look, it's your favorite podcast hosts, Tom Segura and Bert Kreischer! This week in the cave Bert kicks things off with a brand-new joke he swears is the best thing he’s ever written, before diving into an emotional (and hilarious) story about his late bull mastiff, and the wild twist involving the family dog's long-lost sister. From there, the Bears riff on straight cat dads, Bert’s “sleep divorce,” VR porn addictions, childhood prank calls, and even the lost art of memorizing phone numbers. Bert even calls his dead grandma and chit chats with scam caller live on air.
The episode only gets wilder as Tom and Bert review real OnlyFans submissions from fans, debate who should be the first official “2 Bears OF star,” and spiral into some truly insane pitches that only these two maniacs could come up with.
Plus: speech impediments, Elmer Fudd racism, trolling stories, gambling breakdowns from NFL Week 1, and Bert trying to recruit Zac Efron into a shirtless golf fantasy with their new NIL athlete. This might just be the best episode of this show in a long ass time, don’t miss it.
2 Bears, 1 Cave Ep. 306
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:41 - Dogs & Cats
00:08:59 - VR Corn
00:17:30 - Memorizing Geography
00:23:24 - Memorizing Phone Numbers
00:31:35 - Prank Calls
00:37:59 - We Got Some OF Prospects
00:49:50 - Speech Impediments
00:53:45 - NFL Week 1 Gambling
00:59:51 - Bert Wants To Adopt Athletes
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| Is White-Face Cool Again? | 2 Bears, 1 Cave | 08 Sep 2025 | 01:08:07 | |
SPONSORS:
- Don’t miss out on all the action this week at DraftKings! Download the DraftKings app today! Sign-up using https://dkng.co/bears or through my promo code BEARS.
- Don’t let financial opportunity slip through the cracks, get half off your first year with promo code BEARS at https://www.monarchmoney.com/bears
- As always, get your first month of BlueChew FREE Just use promo code BEARS at checkout and pay five bucks for shipping. https://bluechew.com
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- Download the CFO’s Guide to AI and Machine Learning at https://NetSuite.com/BEARS.
We're sorry, guys! Tom and Bert are back in the cave with a full plate: Druski’s viral NASCAR “whiteface” sketch and the art of deep-cover character work, a big “Would you die for your country?” debate, and discuss why streaming giants (Kai, Adin, Jack, etc.) have completely remixed entertainment. Plus, Tom relives an electric college football weekend (FSU at home against Alabama = goosebumps), Bert admits he tried to move a 400-lb armoire and declared himself top 0.5% strong in the city, and the guys hatch a chaotic million-dollar plan to manage an OnlyFans creator—will it work? Is white-face really back? Is Bert making things up? Watch and find out!
2 Bears, 1 Cave Ep. 305
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling problem? Call one eight hundred Gambler. In New York, call eight seven seven eight HOPENY or text HOPENY (four six seven three six nine). In Connecticut, Help is available for problem gambling. Call eight eight eight seven eight nine seven seven seven seven or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Twenty-one plus age and eligibility varies by jurisdiction. Fees may apply in Illinois. Void in Ontario. Bonus bets expire seven days after issuance. See https://sportsbook.draftkings.com/promos. NFL Sunday Ticket offer for new subscribers only and auto-renews until cancelled. Digital games and commercial use excluded. Restrictions apply. Additional NFL Sunday Ticket terms at https://youtube.com/go/nflsundayticket/terms. Limited time offer.
Chapters
00:00:00 - Intro
00:01:30 - Druski Doing White Face
00:10:54 - Streamers Ruined The Military
00:17:32 - Would You Die For Our Country?
00:26:25 - Kam Patterson
00:33:20 - Another Tour
00:38:25 - College Football Weekend
00:49:42 - Let's Become OF Boosters
00:59:17 - Bert's Fight With LeeAnn
01:05:28 - Wrap Up
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| Gambling With Our Lives | 2 Bears, 1 Cave | 01 Sep 2025 | 01:07:26 | |
SPONSORS:
- Don’t miss out on all the action this week at DraftKings! Download the DraftKings app today! Sign-up using https://dkng.co/bears or through my promo code BEARS.
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Bert and Tom are BACK in the Cave! After a memorable summer takeover by Stavvy and Chrissy D, the OG Bears return to catch up on everything—movies, standup, gambling, insane diets, and why Bert can’t stop eating 10 egg bites at once. Tom opens up about his recent cancer-screening scare, which led to a brutal five-day water fast, and accidentally dropping 25 pounds while filming El Tigre. Bert shares why his watch doesn’t fit anymore, how he tormented his director by throwing Liquid Death cans at 4 AM, and the disgusting way he measures his weight.
The Bears also dive into the future of late-night TV, Amy Poehler’s move into podcasting, their own TV and film projects, and Bert’s insane plan to bet $1,000 every week on the Bucs. Plus: family visits on set, Isla living like a diva in Bert’s trailer, Tom’s boys discovering fake cocaine, and both Bears gearing up for the upcoming NFL and NCAA football seasons!
2 Bears, 1 Cave Ep. 304
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Gambling problem? Call one eight hundred Gambler. In New York, call 8778HOPENY or text HOPENY (four six seven three six nine). In Connecticut, Help is available for problem gambling. Call eight eight eight seven eight nine seven seven seven seven or visit ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Fees may apply in IL. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Bonus bets expire seven days after issuance. See sportsbook dot draftkings.com/promos. NFL Sunday Ticket offer for new subscribers only and auto-renews until cancelled. Digital games and commercial use excluded. Restrictions apply. Additional NFL Sunday Ticket terms at https://youtube.com/go/nflsundayticket/terms . Limited time offer.
Chapters
00:00:00 - Intro
00:00:07 - The Final Episode Of 2 Bears
00:09:36 - Tom's New Movie & Free Bert
00:21:47 - Why Tom Got So Skinny
00:33:23 - Bert Is Fat
00:42:04 - Family Visits + America's Team
00:45:48 - Bert's Big Bet
00:54:05 - Is Tom Down?
00:58:49 - A Bert Game Show?
01:01:45 - Wrap Up
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| The Summer Bears Phone It In w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 25 Aug 2025 | 01:07:33 | |
Stavros Halkias Tickets: http://stavvy.biz/tour
Chris Distefano Tickets: https://www.chrisdcomedy.com/tickets
SPONSORS:
- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.
- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
The Summer Bears’ reign has unfortunately come to an end! Stavros Halkias and Chris Distefano return for their last fill-in as hosts of 2 Bears 1 Cave, and they’re going out with a bang. From roasting Tom and Bert’s absence to spiraling into wild tangents about parenting, moving, sex robots, and pie diplomacy with the NYPD, this send-off is chaotic, hilarious, and the perfect finale.
Stavvy and Chrissy talk about the shock of how much fans loved their takeover, whether they’d ever come back as the Fall Bears, and even get Bert on the phone. Tom of course doesn’t pick up. But that's okay, because Mark Normand and Sam Morril crash the party near the end, bringing eclairs and stomach bugs to help close things out.
It’s been a wild six weeks, and the Summer Bears want to leave you with one last memory. You're welcome, f*ckers!
2 Bears, 1 Cave Ep. 303
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:01 - The Summer Bears' Last Dance
00:10:10 - Stoic Shit + Jump Scare Ad Break
00:17:14 - Moving Around & Finding Peace
00:24:12 - Bribing Cops With Pie & Being Addicted To Losing
00:33:06 - ChatGPT Sex Robots
00:41:26 - Swingers & Phoning It In With Bert
00:55:22 - Mark Normand & Sam Morril
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| The Audience Is Gonna Hate Us w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 18 Aug 2025 | 01:15:43 | |
Stavros Halkias Tickets: http://stavvy.biz/tour
Chris Distefano Tickets: https://www.chrisdcomedy.com/tickets
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Stavros Halkias and Chris Distefano return for another sugar-fueled Summer Bears meltdown—this time with bagels, tiramisu, and enough food guilt to keep a Catholic therapist booked for years. The boys break down Chris’ ChatGPT pep talk, reminisce about Stavvy's golden toothless years, and spiral into a deep dive on Neapolitan ice cream fraud, gay NFL cheerleaders, and the politics of bagel orders. Also: Chris reveals his VO2 Max results from a flamboyant fitness coach who may or may not have called him “zaddy.”
2 Bears, 1 Cave Ep. 302
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Chapters
00:00:00 - Intro
00:01:00 - 2 Pigs, 1 Pen
00:12:45 - Catholic Guilt Vs Greek Shame
00:23:33 - Sexual Awakenings In Mom's Bed
00:30:31 - A Demeaning Offer & ChatGPT Pep Talk
00:43:50 - Social Media & Rage For The Gays
00:52:01 - Men In Women's Sports
01:00:02 - Zaddy Chris
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| 2 Bears, 1 Happy Ending w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 11 Aug 2025 | 01:11:01 | |
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The Summer Bears are back and Chris Distefano and Stavros Halkias are fully locked into their takeover of 2 Bears 1 Cave. With Stav in a floral shirt and Chris squeezed into a Darryl Strawberry jersey, the two dive headfirst into tales of the wild ‘86 Mets, Kevin Spacey offering unsolicited shoulder rubs, and the horrifying science of ALS—because what’s funnier than degenerative nerve disease? Stavvy also gets a massage from Chrissy, we learn about Lenny Dykstra's podcast rates, and the guys debate polyamory, prostitutes, and just how many years Bert Kreischer has left.
Speaking of Bert, he sends the guys a morbid video asking them to predict which comedian friends are not long for this world. Plus, Stav makes a strong case for becoming a Japanese-style husband, Chris recounts a near-affair that lasted 12 seconds on the LIRR, and together they fantasize about future threesomes with suspiciously supportive fans.
Is it a good episode? No. Is it packed with fake current events, conspiracy theories, open marriages, and physical touch? You bet your bottom dollar it is.
2 Bears, 1 Cave Ep. 301
https://tomsegura.com/tour
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:42 - Baseball Greats, Kevin Spacey, & ALS
00:10:31 - Reading Fan Comments
00:27:20 - Swingers, Cucks, & Flirty Fans
00:36:33 - Montreal Screwjobs & Polyamory Shenanigans
00:44:58 - Trisha Paytas Baby Theory
00:51:34 - Comedian Death Pool
01:00:49 - Chrissy Massages Stavvy
01:07:23 - Wrap Up
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| Are We Trapped In This Podcast Forever? w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 04 Aug 2025 | 01:11:17 | |
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-Get control of your overall finances with Monarch Money. Use code BEARS at http://monarchmoney.com for half off your first year
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The Summer Bears are back and sweatier than ever as Stavros Halkias and Chris Distefano return to the Cave for a milestone 300th episode that somehow combines deep psychological trauma, ass-eating, and cholesterol awareness in one glorious mess. Chrissy D reveals his shocking bedtime history with his mom, his late-night transition out of her bed, and how a surprise with a tongue changed the trajectory of his life—and his act. Stav explains how a 3XL shirt, childhood grilled cheese binges, and SNL reruns turned him into the hairy Greek sex symbol we know today.
The bears also dive into the state of late night TV (RIP), Jurassic Park boners, and why Bert and Tom might end up bankrupt with nothing but podcast houses and Uncrustables to their name. Plus, an unhinged Monarch Money ad read, BlueChew boners, Turkish military anal policies, and a heartfelt video message from Tom Segura himself. Are the Summer Bears destined to do this foever? Stay tuned!
2 Bears, 1 Cave Ep. 300
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:03:58 - Big Boy Shirts
00:10:15 - Tongue Punch Your Fartbox
00:19:21 - How Did This All Happen?
00:23:48 - Sleeping In Mom's Bed
00:37:17 - Stavvy's Hangups & Chrissy Late Night
00:48:27 - Bowel Movements & Old Sitcoms
00:54:39 - Stav & Chrissy's Movie Corner
01:00:47 - New Jurassic Park
01:05:01 - A Message From Tom Segura
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| This Episode Is Getting Us Fired w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 28 Jul 2025 | 01:08:16 | |
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- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50 percent off plus FREE shipping on your first box.
Stavros Halkias and Chris Distefano are back for round two of Summer Bears—and things spiral immediately. Dressed in their finest “Queens County court appearance” outfits, the guys dive into tales of impersonating cops, awkward court appearances, and Chris’s brief career as a physical therapist (and even briefer run-in with medical malpractice).
The bears get uncomfortably honest about massages that went too far, AI-generated thirst traps, and whether or not Bert and Tom make smashable women. Plus: Stav drops knowledge about Benjamin Franklin’s revolutionary sexcapades, Chris reflects on losing MSG (but gaining perspective), and both dudes debate the pros and cons of fake tits, handy wives, and aging out of horniness.
It’s unhinged, unfiltered, and definitely leading to the hosts getting fired.
2 Bears, 1 Cave Ep. 299
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:08 - Chrissy Court Date
00:06:15 - From Physical Therapy To Comedy
00:18:25 - Happy Ending
00:28:45 - Lady Tom & Bert
00:34:32 - Female Stavvy & Chrissy
00:43:55 - Handy Women & Unhandy Men
00:53:07 - Benjamin Franklin
00:58:32 - MSG
01:03:36 - Wrap Up
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| The Summer Bears Takeover! w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave | 21 Jul 2025 | 01:14:07 | |
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SPONSORS:
- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod
- Sign up for a $1 per month trial period at https://shopify.com/bears
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
Tom and Bert are out for the summer, so Chris Distefano and Stavros Halkias are stepping in as your substitute Bears. In this unhinged takeover, they immediately derail the show with tales of cholesterol-fueled delusion, Nazi neighbors in Queens, circumcision conspiracies, radical acceptance, berberine powder, and why 4th of July is the real American holiday (sorry January 6).
The boys debate who’s the Bert and who’s the Tom in their pairing, accidentally rank the world’s races, and somehow end up talking about diabetes, Greek shame, and Japanese war crimes—all before diving into engagement stories, dad stress, and the magic of getting fat on purpose. Also, Bert checks in from his deathbed to interrupt and tells them to talk about Indian people. This episode is chaos in shorts. True summer vibes. No lessons, no structure—just greasy hot dogs, high blood pressure, and fat guy fun. It's going to be a wild summer!
2 Bears, 1 Cave Ep. 298
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:00 - Who's The Tom & Who's The Bert?
00:08:23 - The Gay Family Man
00:13:56 - Bert's Request
00:21:43 - My War Criminal Neighbor
00:27:19 - Epstein Lists, Toothless Looks, & Fat Guy Speedballs
00:34:49 - We're Just Slowly Dying
00:45:19 - Fourth Of July
00:53:33 - Radical Acceptance
00:58:53 - Chrissy D's Favorite Holiday
01:05:11 - Wrap Up
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| Catfights Make The WNBA Interesting | 2 Bears, 1 Cave | 14 Jul 2025 | 01:14:00 | |
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This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer go deep on sports. They talk about Brett Favre's fall from grace, the greatness of the 2001 Baltimore Ravens, the unbeatable aura of Tony Siragusa, and the dynamic duo of Caitlin Clark and Sophie Cunningham. Before that, Bert shares some stories about going over to T-Pains house. The bears also discuss how violence has made the WNBA more watchable, how good the ESPN "30 For 30" documentaries are, and the most unbelievable races people participate in. Plus: Bert tells a story about how he almost chainsawed a leg off on skates, the Red Bull Flutag, rat catchers, Bert's chicken murder mystery, and more!
2 Bears, 1 Cave Ep. 297
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https://www.bertbertbert.com/tour
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Chapters
00:00:00 - Intro
00:01:17 - T-Pain
00:10:08 - Brett Favre: Hero Or Villain?
00:19:15 - Tony Siragusa & The 2001 Baltimore Ravens
00:30:38 - Caitlin Clark & Sophie Cunningham
00:37:58 - Bert Almost Lost A Leg Skating
00:42:28 - Red Bull Flutag
00:49:23 - The Most Insane Race
00:57:11 - Rat Collectors
01:05:54 - Chicken Murder Mystery
01:11:02 - Wrap Up
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| We're Being Replaced! (For The Summer) | 2 Bears, 1 Cave | 07 Jul 2025 | 01:11:52 | |
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- Make life easier by getting harder and discover your options at https://BlueChew.com! And we’ve got a special deal for our listeners: Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping.
- If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS
- Get a 60-day free trial at https://www.shipstation.com/cave Thanks to ShipStation for sponsoring the show!
This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer reunite in sunny California for a jam-packed episode full of FOMO, fatherhood, and flaming hot air balloon disasters. The bears talk about Tom’s California vacation and getting into surfing with his boys. They dig into wild parenting comparisons, Luis J. Gomez’s insane training routines, and Bert feeling FOMO for Andrew Schulz’s perfect summer life on Instagram.
Tom then drops major news about shooting a new Netflix movie called El Tigre, which leads to Bert sharing his own plans for filming the series Free Bert in Atlanta. With both Bears tied up all summer, they announce special "Summer Bears" episodes and name the two hosts Chris Distefano and Stavros Halkias. Things get political (kind of) as Bert and Tom debate who should talk about world issues—spoiler alert: it’s not them. Bert then rants about the sheer terror of hot air balloons and Tom tells another legendary Top Dog tale about how he diverted a plane so he could take a piss. Buckle up—it’s a bumpy (and hilarious) ride.
2 Bears, 1 Cave Ep. 296
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:40 - Father FOMO
00:05:07 - The Summer Bears
00:16:45 - FaceTiming Chrissy D
00:20:16 - The Middle Class Of Comedy
00:33:09 - Bert Explains Global Politics
00:39:48 - Hot Air Balloons Are Sketch
00:49:29 - Crazy Plane Stories
01:00:17 - Helicopters
01:06:45 - Uber Driver Smackdown
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