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.
Episodes
What Hollywood Doesn't Want You to Notice | Conrad Flynn
In this episode of Trying Not to Die, Jack Osbourne sits down with Conrad Flynn for a fascinating conversation that explores the hidden connections between Hollywood, rock music, Silicon Valley, spirituality, and American culture. Drawing from years of research and personal experiences growing up around the entertainment industry, Conrad shares stories that challenge conventional narratives and re
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 proce
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
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 everythi
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
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 a
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. Togethe
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 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
Chris D'Elia on Addiction, Accountability, and What Comes After Losing Everything
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
I'm A Celebrity, Get Me Out Of Here: Jack Osbourne's Full Recap
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.
Jim Curtis Cures Jack's Fear of Spiders
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 li
Kelly Rizzo Is Moving Forward, Not Moving On
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 No
Louis Osbourne Tries Not To Die: Triathlons, DJ Sets and Life Inside the Hurricane
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 produ
Derek Moneyberg Goes Five Rounds with Jack and Ryan
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 Ca
Nick Viall on Why Your Friends Give Bad Advice & Finding Peace Post-Bachelor
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 h
Yungblud Tries Not to Die: Boxing, Boots, BBQ & Real Rock N Roll
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 ☕. Powe
Sean Avery on NHL Hockey Brawls, New York Chaos & Writing Romance Novels | Jack Osbourne Podcast
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 fr
Why Men Are Getting Plastic Surgery & How Dr. Jason Diamond Plans to Live Forever | Jack Osbourne
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 J
Jocko Willink Tries Not to Die: Black Sabbath, Drone Warfare & Jujitsu
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
Series Trailer
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,
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