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.

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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.

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.

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Music by Ryan Hahn.

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.

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Music by Ryan Hahn.

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.

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Music by Ryan Hahn.

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.

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Music by Ryan Hahn.

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
0:45 Meeting Chris D'Elia & warming up
2:25 Why this podcast exists: "Trying Not To Die"
3:30 Becoming a father and finally wanting to live
5:20 Health anxiety, full-body scans, and fear of dying
7:40 Fame, sex, validation, and default settings
10:00 Chris's father, cancer, and why he watches his health
12:30 Sex as a drug and chasing approval
15:00 Performing so you don't have to feel
17:00 Touring, travel, and being away from family
19:00 Flying, airports, and why nobody can reach you
22:30 Hotels, road life, and stand-up survival
25:15 Losing friends when everything fell apart
27:30 Public backlash vs real life
29:30 Sex addiction, lying, and double lives
32:00 Rehab, recovery, and learning to be honest
34:15 OCD, anxiety, and living in your head
36:00 Childhood, fear, and creativity
38:30 Trauma, therapy, and learning who you really are
40:15 Tattoos, identity, and starting over
42:30 How Chris writes comedy
44:30 Crowd work vs real stand-up
47:00 Fame, fans, and misunderstanding online
49:00 Ozzy Osbourne, comedy, and Rodney Dangerfield
53:20 Going back on stage after everything collapsed
55:40 Death threats, thick skin, and ego death
58:00 Jiu-Jitsu, discipline, and getting out of your head
1:01:30 Honesty, secrets, and self-worth
1:04:00 Being funny at home and with kids
1:07:30 Loyalty, marriage, and rebuilding trust
1:11:00 Sex addiction, celibacy, and real intimacy
1:15:00 The movie Shame and seeing your past
1:18:30 Masculinity, integrity, and changing as a man
1:22:00 There is a way out
1:25:30 Mike Tyson, ego, and not needing approval
1:27:30 Final thoughts & goodbye

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

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Support Our Sponsors:

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- 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!

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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 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:
👻 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

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Executive Producers: Natalie Holysz and Rob Holysz
Associate Producer: Jesse Thurston
Video Editor: Tricia Scully
Mix & Master: Cheyenne Jones