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Trying Not To Die: Daily Summaries Delivered
by Jack Osbourne
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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 1 weeks ago59 min
Paris Jackson On Grief, Music & Growing Up In The Spotlight
In this episode of Trying Not to Die, Jack Osbourne sits down with Paris Jackson for a raw and deeply personal conversation about grief, identity, addiction, mental health, and growing up under unimaginable public scrutiny. Paris opens up about the pressure of carrying one of the most famous last names in the world, the challenges of finding herself outside public perception, and the ongoing process of healing through music, spirituality, creativity, and recovery. From childhood memories and personal loss to self-acceptance and rebuilding her life on her own terms, this episode explores what it means to survive while learning how to truly live.
- 3 weeks ago1h 33m
Cory Richards On Climbing Everest and Losing Control
In this episode of Trying Not to Die, Jack Osbourne sits down with legendary climber and photographer Cory Richards for a raw conversation about survival, addiction, trauma, and identity. Cory opens up about bipolar disorder, near-death experiences, chasing purpose through extreme adventure, and the emotional crash that followed some of the biggest accomplishments of his life, including summiting Everest. From avalanches and fame to recovery and rebuilding himself off the mountain, this episode explores what happens when surviving the impossible still isn't enough to save you. 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 -Go to AquaTru.com now for 20% off (your purifier) using promo code TRYING Music by Ryan Hahn.
- Apr 28, 20261h 7m
Howie Mandel Talks OCD and Conspiracy Theories
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with the legendary Howie Mandel for one of the most honest and eye-opening conversations yet. Howie opens up about living with OCD, anxiety, and intrusive thoughts, and what it's really like inside his mind. From debilitating panic attacks to years of hiding his diagnosis, he shares how a moment on radio changed everything and helped him realize he wasn't alone. The conversation dives deep into mental health, fear, and the reality of coping with something that doesn't just "go away." Howie explains the difference between everyday habits and true OCD, and why understanding that distinction matters more than people think. Along the way, the conversation touches on growing up without mental health awareness, coping with germophobia, raising kids with similar struggles, and the importance of removing the stigma around mental health. Howie offers a powerful perspective on fear. Not as something to avoid, but as the very force that drives people forward in life. Thank you to our sponsors: -Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order. -Start your new morning ritual & get up to 43% off your @MUDWTR with code TRYING at mudwtr.com/TRYING! #mudwtrpod #ad
- Apr 14, 20261h 42m
Jim Norton Gets Real: Sobriety at 18, Self-Doubt & Comedy
In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with comedian and longtime friend Jim Norton for one of the most brutally honest conversations yet. Jim opens up about getting sober at just 18 years old, why he still struggles with self-worth decades later, and how shame, addiction, and impulse control have shaped his life both on and off stage. From sex addiction and dopamine-driven habits to the reality of long-term recovery, this is a raw, unfiltered look at what it actually means to "work on yourself." The conversation dives deep into relationships, communication, and the damage that can come from saying things you can't take back, as well as the discipline it takes to stop yourself in the moment. Jim also shares his thoughts on confidence, comedy, and why he's never fully believed in his own success despite a massive career. Presented by Caveman Coffee https://www.DRINKCAVEMAN.COM ☕. Powered by Osbourne Media.
- Mar 31, 20261h 5m
Dan MacPherson On Acting, MMA Training, Ironman & Mental Health
In this episode of Trying Not To Die, hosts Jack Osbourne and Ryan Drexler sit down with actor and endurance athlete Dan MacPherson for a deep dive into discipline, identity, and what it really takes to push your limits. Dan shares his journey from starring on Neighbours to competing at Ironman world championship level, and eventually transforming his body and mindset for intense Hollywood roles alongside Russell Crowe. The conversation explores the brutal reality of training for MMA film roles, the mental and physical demands of high-performance acting, and the lessons learned from years of endurance sports. They also get into the deeper side of life, including why your late 30s and early 40s can feel like the hardest years, the shift from boyhood to manhood, and the struggle of maintaining purpose and identity through major life transitions. Dan opens up about balancing fatherhood, career, and health, while emphasizing the importance of discipline, routine, and staying grounded. 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.
- Mar 3, 20261h 12m
Inside Harley & Tattoo Culture | Brian & Mark Vaillancourt
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.
- Feb 17, 20261h 59m
Jamie Kennedy UNFILTERED: ICE, Hollywood Hypocrisy & The Collapse of LA
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.
- Feb 3, 20261h 31m
The UAP Truth Finally Comes Out with Dan Farah
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 And use code TRYING to Save $30 Off + Free Shipping. USA Residents Only Music by Ryan Hahn.
About Trying Not To Die
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.
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