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...
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Sep 29, 2026 · 1:00:24
Hunter Biden joins Jack Osbourne for a deeply personal conversation about addiction, recovery, family, and what it is like to have your private struggles become national news.…
Sep 15, 2026 · 56:31
On this episode of Trying Not To Die, Tyler Henry joins Jack Osbourne for a fascinating conversation about death, the afterlife, mediumship, and what happens when we leave this…
Sep 1, 2026 · 1:13:55
On this episode of Trying Not To Die, evangelical street preacher Bryce Crawford joins Jack Osbourne for a wide-ranging conversation about Christianity, faith, suffering, and the…
Aug 18, 2026 · 56:08
On this episode of Trying Not To Die, Billy Morrison joins Jack Osbourne for an unforgettable conversation about addiction, recovery, music, and the extraordinary journey that…
Aug 4, 2026 · 1:02:32
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…
Jul 21, 2026 · 57:54
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…
Jul 7, 2026 · 1:00:02
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…
Jun 23, 2026 · 32:49
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…
Jun 9, 2026 · 1:06:27
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,…
May 26, 2026 · 59:46
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…
May 12, 2026 · 1:33:57
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…
Apr 28, 2026 · 1:07:11
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…
Apr 14, 2026 · 1:42:46
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.…
Mar 31, 2026 · 1:05:56
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…
Mar 3, 2026 · 1:12:57
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…
Feb 17, 2026 · 1:59:12
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…
Feb 3, 2026 · 1:31:55
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…
Jan 13, 2026 · 1:29:12
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…
Dec 30, 2025 · 1:00:03
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.…
Dec 16, 2025 · 1:04:22
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…
Dec 2, 2025 · 1:02:14
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…
Nov 18, 2025 · 1:07:31
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…
Nov 4, 2025 · 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…
Oct 21, 2025 · 1:00:11
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…
Oct 7, 2025 · 1:02:10
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…
Sep 9, 2025 · 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…
Jul 15, 2025 · 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…
Jul 1, 2025 · 1:09:27
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…
Jun 29, 2025 · 0:55
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,…
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