Explore every episode of the podcast Trying Not To Die
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Derek Moneyberg Goes Five Rounds with Jack and Ryan | 04 Nov 2025 | 00:59:55 | |
Businessman Derek Moneyberg shocked the Brazilian Jiu Jitsu community when he was awarded his black belt by Jake Shields after only 3 years. Jack and Ryan talk with him about the controversy, what he's learned from training with the best and his keys to success on the mat and in business. Plus, Derek issues a challenge to Sean Strickland and invites the guys to join him in the gym. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch Trying Not to Die on YouTube: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. ------------------------- About the show: From mad-scientist doctors and longevity junkiesd to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Find Jack: ------------------------ Executive Producers: Natalie Holysz and Rob Holysz | |||
| Nick Viall on Why Your Friends Give Bad Advice & Finding Peace Post-Bachelor | 21 Oct 2025 | 01:00:11 | |
Jack Osbourne and Ryan Drexler are joined by reality TV star turned podcast mogul Nick Viall. Nick talks about translating success on The Bachelor into a successful career as an author (Don't Text Your Ex Happy Birthday) and podcast host, with his hit show, The Viall Files. He drops wisdom on the do's and don'ts of DM'ing, fatherhood and maintaining his mental health. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. ------------------------- About the show: From mad-scientist doctors and longevity junkiesd to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Find Jack: ------------------------- 0:00 Intro 00:33 Hello Nick Viall ------------------------- Executive Producers: Natalie Holysz and Rob Holysz #nickviall #MensHealth #jackosbourne #thebachelor #mentalhealth #datingadvice | |||
| Yungblud Tries Not to Die: Boxing, Boots, BBQ & Real Rock N Roll | 07 Oct 2025 | 01:02:10 | |
Yungblud takes a break from touring to visit with Jack Osbourne and Ryan Drexler. They break down the VMAs' tribute to the late Ozzy Osbourne, how Yungblud is carrying on his legacy and the time Ozzy made him a salami sandwich. Plus, dealing with online hate, hitting rock bottom, the glory of Chinese food and boxing with Peter Berg. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.com ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Ready to level up your confidence in the bedroom? Head to https://www.rugiet.com and use promo code TRYING for 15% off your first order. - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. ------------------------- About the show: Trying Not to Die is a bi-weekly video podcast hosted by Jack Osbourne and Ryan Drexler, where caffeine meets chaos and survival is the point. Expect unfiltered conversations, high-performance hot takes, and deep dives into aging, recovery, wellness, mental performance and everything we're doing to cheat death (or at least slow it down). From mad-scientist doctors and longevity junkiesd to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Watch more from Jack: 👻 The Most Haunted ⮕ https://www.youtube.com/playlist?list=PLEc6TASrXh3eZFzsxuv0YyZPCZS77tL2v ⚔️ Ghost and Grit ⮕ https://www.youtube.com/playlist?list=PLEc6TASrXh3fJvwuZTOQ9JibZUdgNy8oO Find Jack: ⮕ Osbourne Media House: https://osbournemediahouse.com/ ⮕ Instagram: https://www.instagram.com/jackosbourne/ ⮕ TikTok: https://www.tiktok.com/@ghostsandgrit ⮕ Facebook: https://www.facebook.com/JackOsbourneOfficial ⮕ Twitter: https://twitter.com/JackOsbourne ------------------------- 0:00 Intro 0:39 Broccoli and Mullets 2:07 Yungblud US Tour 5:16 Back to the Beginning 13:18 Boxing and Jiu Jitsu 21:41 Instant Validation 24:53 Ozzy Was My Batman 28:04 Health and Accountability 34:58 Trolls at the VMAs 42:57 Ozzy's Legacy 46:08 Yungblud's Biggest Meltdown 49:04 Everyone's Equal at the Gym 55:01 European Tour Kickoff ------------------------- Executive Producers: Natalie Holysz, Rob Holysz & Jeph Porter Creative Producer: Jesse Thurston Video Editor: Tricia Scully Mix & Master: Cheyenne Jones #yungblud #MensHealth #ozzyosbourne #jackosbourne #vmas | |||
| Sean Avery on NHL Hockey Brawls, New York Chaos & Writing Romance Novels | Jack Osbourne Podcast | 09 Sep 2025 | 00:54:35 | |
Sean Avery joins Jack Osbourne and Ryan Drexler on the Trying Not To Die Podcast to talk hockey brawls, New York chaos, and his unexpected role as a romance novelist. From NHL fights and celebrity encounters to Vogue internships and jiu-jitsu training, Avery proves why he's the ultimate cultured barbarian. Presented by Caveman Coffee www.CAVEMANCOFFE.COM ☕. Powered by Osbourne Media. Watch more from Jack: 👻 The Most Haunted ⮕ https://www.youtube.com/playlist?list=PLEc6TASrXh3eZFzsxuv0YyZPCZS77tL2v ⚔️ Ghost and Grit ⮕ https://www.youtube.com/playlist?list=PLEc6TASrXh3fJvwuZTOQ9JibZUdgNy8oO Find Jack: ⮕ Osbourne Media House: https://osbournemediahouse.com/ ⮕ Instagram: https://www.instagram.com/jackosbourne/ ⮕ TikTok: https://www.tiktok.com/@ghostsandgrit ⮕ Facebook: https://www.facebook.com/JackOsbourneOfficial ⮕ Twitter: https://twitter.com/JackOsbourne #Longevity # NYRANGERS #Summerskate #seanavery #MensHealth #fitness #culturedbarbarian #jackosbourne Need Delicious Coffee? Go to www.cavemancoffee.com and get 15% off on your first order. | |||
| Why Men Are Getting Plastic Surgery & How Dr. Jason Diamond Plans to Live Forever | Jack Osbourne | 15 Jul 2025 | 00:56:31 | |
Celebrity surgeon Dr. Jason Diamond joins the show to talk immortality science, plastic surgery for men, and why your muscle tissue might be the key to not dying ugly. We get into club trauma, Celsius addiction, the science of aging, and whether lifting weights is better than injecting your face. Also: 80s cars, strange bets, and the IROC-Z camera incident. Powered by Caveman Coffee You can find Jack at:⮕ YouTube ⮕ Patreon ⮕ TikTok | |||
| Jocko Willink Tries Not to Die: Black Sabbath, Drone Warfare & Jujitsu | 01 Jul 2025 | 01:09:27 | |
n the debut episode of Trying Not To Die, Navy SEAL and discipline king Jocko Willink drops in for a wildly unpredictable conversation about Jiu jitsu, drone warfare, modern masculinity, and his deep love for Black Sabbath. We talk about why war is now content creation, what it takes to stay calm in chaos, and how Jocko got completely starstruck meeting Tony Iommi. Powered by Caveman Cofee You can find Jack at:⮕ YouTube ⮕ Patreon ⮕ TikTok
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| Series Trailer | 29 Jun 2025 | 00:00:55 | |
Trying Not to Die is a bi-weekly video podcast hosted by Jack Osbourne and Ryan Drexler, where caffeine meets chaos and survival is the point. Expect unfiltered conversations, high-performance hot takes, and deep dives into aging, recovery, wellness, mental performance and everything we're doing to cheat death (or at least slow it down). From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Powered by Cave Man Coffee. Powered by Caveman Coffee Episodes drop bi-weekly starting July 1st. You can find Jack at: Produced By Osbourne Media, LLC.
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| Louis Osbourne Tries Not To Die: Triathlons, DJ Sets and Life Inside the Hurricane | 18 Nov 2025 | 01:07:31 | |
Jack's brother Louis Osbourne stops by the show. Together, they remember Ozzy, including tales from the road, the first time he met Axl Rose and the truth about those seventeen cats. Plus, Louis and Jack share details of the massive outpouring of support at the Cortege in Birmingham. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. - For a limited time, our listeners get 60% off FOR LIFE AND 2 Free Gifts at Mars Men when you use code TRYING at https://www.mengotomars.com - Ready to level up your confidence in the bedroom? Head to https://www.RUGIET.com and use promo code TRYING for 15% off your first order. - Today, get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code TRYING at https://huel.com/TRYING (Minimum $75 purchase). ------------------------- About the show: From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Watch more from Jack: Find Jack: ------------------------- Executive Producers: Natalie Holysz and Rob Holysz | |||
| Kelly Rizzo Is Moving Forward, Not Moving On | 02 Dec 2025 | 01:02:14 | |
Kelly Rizzo is a food blogger and the founder of the online support community Comfort Club. She joins Jack and Ryan to discuss grieving in public after the death of her husband Bob Saget and the ways gratitude, dumb jokes, good food and new love have helped her rebuild her life after devastating loss. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. - For a limited time, our listeners get 60% off FOR LIFE AND 2 Free Gifts at Mars Men when you use code TRYING at https://www.mengotomars.com - Today, get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code TRYING at https://huel.com/TRYING (Minimum $75 purchase). ------------------------- About the show: From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Watch more from Jack: Find Jack: ------------------------- 00:00 Hello Kelly Rizzo ------------------------- Executive Producers: Natalie Holysz and Rob Holysz | |||
| Jim Curtis Cures Jack's Fear of Spiders | 16 Dec 2025 | 01:04:22 | |
Jim Curtis has had a long career as a coach, hypnotherapist and spiritual educator, but his recent relationship with Jennifer Aniston put him on the tabloid radar for the first time. Jack and Ryan learn more about Jim's journey of self-transformation and the tools he uses with his clients, from hypnosis and NLP to psychedelics and positivity. Plus, watch as Jim eliminates Jack's fear of spiders live on camera. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. - For a limited time, our listeners get 60% off FOR LIFE AND 2 Free Gifts at Mars Men when you use code TRYING at https://www.mengotomars.com - Ready to level up in the bedroom? Head to https://www.Rugiet.com/TRYING for 15% off your order - Today, get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code TRYING at https://huel.com/TRYING (Minimum $75 purchase). ------------------------- About the show: From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Watch more from Jack: Find Jack: ------------------------- Executive Producers: Natalie Holysz and Rob Holysz | |||
| I'm A Celebrity, Get Me Out Of Here: Jack Osbourne's Full Recap | 30 Dec 2025 | 01:00:03 | |
Jack and Ryan cover Jack's recent stint in the jungle. He dishes on becoming the reluctant leader at camp, fabricated "beef" with Aitch and how Taylor Swift led to his downfall. Plus, find out if Jim Curtis' hypnosis actually worked. Presented by Caveman Coffee https://www.CAVEMANCOFFEE.COM ☕. Powered by Osbourne Media. Trying Not To Die is produced by Rabbit Grin Productions. Music by Ryan Hahn. Watch more Trying Not to Die: https://www.youtube.com/playlist?list=PLEc6TASrXh3fB645U2_3u8t12dazkpSl1 ------------------------- Support Our Sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. - Get Huel's full High-Protein Starter Kit with my exclusive offer of 20% OFF online with my code TRYING20 at https://www.huel.com/TRYING20. New Customers Only. Code only valid for the bundle. Thank you to Huel for partnering and supporting our show! ------------------------- About the show: From mad-scientist doctors and longevity junkies to artists, athletes, and off-beat thinkers, Jack and Ryan explore what it really takes to stay strong, sharp, and a little wild in your 20s, 30s, 40s, and beyond. This isn't a self-help show, it's a low-pressure hang with two curious minds, trying new things and asking the questions we all wonder but rarely say out loud. Watch more from Jack: Find Jack: ------------------------- Executive Producers: Natalie Holysz and Rob Holysz | |||
| The UAP Truth Finally Comes Out with Dan Farah | 03 Feb 2026 | 01:31:55 | |
On this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with filmmaker Dan Farah, producer of Ready Player One and director of one of the most serious and credible documentaries ever made on UAPs, UFOs, and non-human intelligence, The Age of Disclosure. Dan reveals how he spent years building trust with high-level military, intelligence, and government officials, many of whom had never spoken publicly before, to uncover what he describes as an 80-year cover-up involving crashed UAPs, non-human technology, and a secret global race to reverse engineer it.
Thank you to our sponsors: - Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order. -Rula patients typically pay $15 per session when using insurance. Connect with quality therapists and mental health experts who specialize in you at https://www.rula.com/TRYING #rulapod #ad -Head to Superpower.com and use code TRYING at checkout for $20 off your membership. Live up to your 100-Year potential. #superpowerpod -Get up to 39% off your Mitopure Gummies at Timeline.com/TRYING -Stay ahead of sickness this winter with the Medical Emergency Kit. Visit www.twc.health/trying
Music by Ryan Hahn. | |||
| Chris D'Elia on Addiction, Accountability, and What Comes After Losing Everything | 13 Jan 2026 | 01:29:12 | |
Chris D'Elia joins Jack Osbourne for a deeply honest conversation about sex addiction, recovery, ego death, and rebuilding a life after everything falls apart. In this episode of Trying Not to Die, Jack Osbourne sits down with comedian and actor Chris D'Elia for a raw, wide-ranging conversation about addiction, shame, recovery, and what happens when a life built on secrets finally collapses. Chris opens up about his struggles with sex addiction, compulsive behavior, and the lies he told himself while living in the spotlight. He talks about losing everything, facing public backlash, going to rehab, attending meetings, and what it means to try to rebuild a life based on honesty instead of impulse. Together, Jack and Chris discuss ego death, fame, fatherhood, loyalty, and why becoming a husband and a parent forced Chris to finally confront himself. They also explore how creativity, comedy, and performance can be both a lifeline and a hiding place — and how learning to sit with discomfort is part of real recovery. This is not a conversation about cancel culture or redemption. It's about responsibility, growth, and whether it's possible to live without secrets when you no longer want to run from yourself. Listener discretion advised. 0:00 Intro & Caveman Coffee | |||
| Jamie Kennedy UNFILTERED: ICE, Hollywood Hypocrisy & The Collapse of LA | 17 Feb 2026 | 01:59:12 | |
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with comedian and actor Jamie Kennedy for one of their most unfiltered conversations yet. Jamie breaks down how he's trying not to die, from walking 10,000 steps a day and eating cleaner to experimenting with cold plunges, breathwork, and the shift from drinking culture to wellness culture. The three dive headfirst into the heated debates surrounding ICE, immigration, homelessness in Los Angeles, law enforcement, and what they see as growing hypocrisy within Hollywood. Jamie shares his perspective on America, current events, and why he believes many people don't realize how good they have it.
Thank you to our sponsors: -Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. -Don't sleep on @ultrapouches. New customers get 15% Off with code TRYING at takeultra.com! #UltraPouches #ad -For a limited time, our listeners get 50% off FOR LIFE, Free Shipping, AND 3 Free Gifts at Mars Men at Mengotomars.com -Get up to 39% off your Mitopure Gummies at Timeline.com/TRYING -Spike Detox your body! Click http://www.twc.health/trying and use code TRYING for 10% Off + Free Shipping for USA residents
Music by Ryan Hahn. | |||
| Inside Harley & Tattoo Culture | Brian & Mark Vaillancourt | 03 Mar 2026 | 01:12:57 | |
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler dive deep into motorcycle and tattoo culture with brothers Brian Vaillancourt and Mark Vaillancourt. Brian and Mark Vaillancourt are brothers deeply rooted in motorcycle and tattoo culture, known for their passion for Harleys, club rides, and the lifestyle that comes with being fully immersed in ink and biker communities. Together they represent a blend of brotherhood, identity, and subculture perspective that bridges tattoo art with the open-road ethos of modern motorcycle life. The brothers break down how they got heavily tattooed starting at 18, the decision to go fully covered, the crossover between biker culture and tattooes, and how society reacts when you're tattooed from head to toe. There's also honest discussion about club life, perception vs reality, stereotypes about prison ink, and how the culture has shifted over the decades.
Thank you to our sponsors: - Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. -Get up to 39% off your Mitopure Gummies at Timeline.com/TRYING
Music by Ryan Hahn. | |||