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Trying Not To Die

Jack Osbourne
Trying Not To Die
Latest episode

25 episodes

  • Trying Not To Die

    Robert Trujillo On Ozzy, Metallica & The Stories You've Never Heard

    08/04/2026 | 1h 2 mins.
    In this episode of Trying Not to Die, Jack Osbourne sits down with Robert Trujillo for an unforgettable conversation about Metallica, Ozzy Osbourne, and one of the most remarkable careers in rock music. Robert reflects on his journey from the Los Angeles music scene to Suicidal Tendencies, Ozzy's band, and ultimately Metallica, sharing behind-the-scenes stories from every chapter along the way. He also opens up about his close relationship with Ozzy, the lasting bond between their families, and the unexplained paranormal experiences that left a lasting impression on him.
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    Thank you to our sponsors:
    - Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order.
  • Trying Not To Die

    The Paranormal, Ego & Psychedelics | Jack Osbourne and Keith Crossley

    07/21/2026 | 57 mins.
    In this episode of Trying Not to Die, Jack Osbourne sits down with relationship coach Keith Crossley for a powerful conversation about the unconscious patterns that shape our lives and why so many people struggle to break free from fear, anxiety, and self-sabotage. Keith shares the personal journey that led him to rethink everything he believed about healing, offering a framework for understanding the ego, trauma, and the root causes behind emotional suffering. Together they explore meditation, spirituality, relationships, grief, consciousness, and the mindset shifts that can lead to lasting personal transformation.
    Ā 
    Thank you to our sponsors:
    - Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order.
    - If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: https://learn.nocd.com/trying
    - Get up to $200 off Square hardware when you sign up at square.com/go/trying! #squarepod #ad
  • Trying Not To Die

    Billy Bush On Losing Everything and Starting Over

    07/07/2026 | 1h
    In this episode of Trying Not to Die, Jack Osbourne sits down with Billy Bush for a brutally honest conversation about public failure, redemption, and rebuilding a life after everything changes overnight. Billy opens up about the fallout from 2016, what he learned from becoming the center of a global media firestorm, and how that experience reshaped his perspective on success, forgiveness, and happiness. The conversation also explores addiction recovery, psychedelics, podcasting, the modern media landscape, and the importance of staying true to yourself when the world has already decided who you are.
    Ā 
    Thank you to our sponsors:
    - Need Delicious Coffee? Go toĀ https://www.drinkcaveman.com and use code trying15 for 15% off your first order.
    -If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started:Ā https://learn.nocd.com/trying
  • Trying Not To Die

    My Wife and I Respond To Our Date At The White House UFC Fight & Why We Went | Jack & Aree Osbourne

    06/23/2026 | 32 mins.
    In this episode of Trying Not to Die, Jack Osbourne and his wife Aree break down their experience attending the highly talked about UFC event at the White House and the unexpected backlash that followed. They share what it was actually like behind the scenes, from the atmosphere and security to the celebrities, athletes, and unforgettable moments that made the night feel surreal. The conversation dives into the online reaction they received afterward, why they chose to attend, and how quickly people can jump to conclusions based on a single photo or headline.
  • Trying Not To Die

    What Hollywood Doesn't Want You to Notice | Conrad Flynn

    06/09/2026 | 1h 6 mins.
    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 reveal unexpected links between some of the most influential people, movements, and moments of the last century. From old Hollywood legends and the counterculture era to technology, faith, and the nature of coincidence itself, this episode is a deep dive into the stories behind the stories and the forces that continue to shape the modern world.
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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. Powered by Cave Man Coffee.
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