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

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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

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

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 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

- 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

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00:00 Hello Kelly Rizzo 00:51 Remembering Special Forces 05:40 Easier Now To Eat Well 11:13 Michelin Restaurants 14:28 Bob Saget's DM Game 19:46 Grief Isn't Linear 24:28 I Didn't Believe It Was Real 30:10 Gratitude Was Huge 37:02 Bob's Supportive Community 42:05 Comfort Club 48:28 Bob and John Stamos 53:50 The Aristocrats and Big Lebowski 59:53 Staying Positive

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

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 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 your confidence in the bedroom? Head to https://www.RUGIET.com and use promo code TRYING for 15% off your first 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

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

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 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 Trying Not to Die on YouTube: 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.

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

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 junkiesd 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.

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

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 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.

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

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 junkiesd 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.

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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0:00 Intro

00:33 Hello Nick Viall 03:22 Translating Bachelor Success 07:49 Controlling the Edit 14:01 I Wasn't Lonely 19:00 They're Not All Your Type 23:04 Mental Health in Reality TV 27:40 Learning to Eat Right 35:30 Letting Go of Ego 38:37 Know Who to Ask For Advice 42:09 The Art of The DM 46:46 Fatherhood Changes Things 52:23 Wisdom from Ozzy 55:05 Don't Lose Your Joy

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

#nickviall #MensHealth #jackosbourne #thebachelor #mentalhealth #datingadvice

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 ☕. 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:

- Ready to level up your confidence in the bedroom? Head to https://www.rugiet.com and use promo code TRYING for 15% off your first order.

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

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

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 junkiesd 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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0:00 Intro

0:39 Broccoli and Mullets

2:07 Yungblud US Tour

5:16 Back to the Beginning

13:18 Boxing and Jiu Jitsu

21:41 Instant Validation

24:53 Ozzy Was My Batman

28:04 Health and Accountability

34:58 Trolls at the VMAs

42:57 Ozzy's Legacy

46:08 Yungblud's Biggest Meltdown

49:04 Everyone's Equal at the Gym

55:01 European Tour Kickoff

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Executive Producers: Natalie Holysz, Rob Holysz & Jeph Porter

Creative Producer: Jesse Thurston

Video Editor: Tricia Scully

Mix & Master: Cheyenne Jones

#yungblud #MensHealth #ozzyosbourne #jackosbourne #vmas

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 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

#Longevity # NYRANGERS #Summerskate #seanavery #MensHealth #fitness #culturedbarbarian #jackosbourne

Need Delicious Coffee? Go to www.cavemancoffee.com and get 15% off on your first order.

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 Jack at:

⮕ Osbourne Media House

⮕ YouTube

⮕ Patreon

⮕ Instagram

⮕ Facebook

⮕ Twitter

⮕ TikTok