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:

- Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order.

- 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

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 live on camera.

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

-------------------------

Support Our Sponsors:

- Need Delicious Coffee? Go to https://www.cavemancoffee.com and use code trying15 for 15% off your first order.

- For a limited time, our listeners get 60% off FOR LIFE AND 2 Free Gifts at Mars Men when you use code TRYING at https://www.mengotomars.com

- Ready to level up in the bedroom? Head to https://www.Rugiet.com/TRYING for 15% off your order

- Today, get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code TRYING at https://huel.com/TRYING (Minimum $75 purchase).

-------------------------

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

-------------------------

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