Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)

Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)

Have you ever failed at something you really wanted?

What did that experience teach you about yourself?

Today, Jay chats with late-night legend Jimmy Kimmel for an unforgettable live conversation at the Greek Theatre in Los Angeles. Jimmy opens the episode playfully roasting Jay, showing off his signature, sharp wit right out of the gate. The laughs quickly give way to a candid, wide-ranging conversation about Jimmy’s life, marked by gutsy decisions, constant reinvention, and moments of surprising vulnerability.

Jimmy reflects on the emotional cost of self-expression, his early struggles with being misunderstood, and how persistence (and a healthy dose of delusion) helped him find his place in the world. Jimmy shares how anxiety has shaped his life, from growing up without much money to now being someone people rely on for support, advice, and even financial help. From outrageous pranks and career missteps to a touching tribute to his prank-loving Aunt Chippy, Jimmy constantly balances humor with disarming honesty. Jimmy also opens up about the challenges of becoming more emotionally available, how therapy has helped him grow, and how being a father, and now a grandfather, has reshaped his priorities and softened his edges.

In this interview, you'll learn:

How to Stay True to Yourself

How to Use Humor as a Tool for Healing

How to Keep a Lifelong Passion Alive

How to Stay Grounded When Success Finds You

How to Cope With Anxiety Through Creative Outlets

How Helping Others is the Key to Healing Yourself

It’s not about being perfect, it’s about being honest, showing up, and continuing to try. Whether through meaningful conversations, creative expression, or simply sharing space with others, healing and connection are always within reach.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

What We Discuss:

00:00 Intro

04:44 Why is Putting Yourself Out There So Hard?

08:00 Discovering What Truly Drives You

09:19 The Origins of Jimmy’s Legendary Pranks

11:56 When the Pranks Never Stop

17:02 Failed Firings and Conversations That Went Sideways

18:30 Staying True to Your Creative Voice

21:42 Becoming a Grandfather for the First Time

25:55 Living With Anxiety: How It Shapes Family Life

27:29 Jimmy’s Take on Managing Anxiety

29:56 What It’s Like to Face Financial Pressure

31:17 How Jimmy Met the Love of His Life

32:31 Is Finding Love in LA Really That Hard?

33:17 The Secret to a Strong and Lasting Marriage

38:19 Why Talking About Your Feelings Is So Tough

39:16 What To Do When You’re Feeling Low

43:05 Jimmy on Final Five

Episode Resources:

Jimmy Kimmel | Instagram

Jimmy Kimmel | Facebook

Jimmy Kimmel | YouTube

Jimmy Kimmel | X

Jimmy Kimmel | TikTok

See omnystudio.com/listener for privacy information.

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Lilly Singh: ON Why She Took A Break From YouTube

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3 Lessons I Learned From My Ex

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Breakups are hard there’s no doubt about that, but sometimes break-ups lead to break-throughs. Don’t worry, it’s normal to have feelings of bitterness, blame, or even have a breakdown. You are not alone.We cover a lot in today’s episode so whether you’re looking to strengthen your current relationship or need a little help getting through a past one you’re not going to want to miss this.See omnystudio.com/listener for privacy information.

22 Feb 201927min

Novak Djokovic: ON One of the Greatest Comebacks in History

Novak Djokovic: ON One of the Greatest Comebacks in History

Most people, even non-sports fans are inspired by world class athletes like Novak… but why?To be world class at anything it takes more than natural skill, it takes physical, personal, spiritual development and a healthy relationship with one’s own ego to begin a fulfilling journey to greatness - something we are all capable of, given we know how to use the appropriate tools.In today’s conversation, Novak shares everything.He even takes us back to his childhood where he remembers confiding to his tennis coach instead of his own parents about the growing pains of being a young man.See omnystudio.com/listener for privacy information.

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Jay Shetty Interviews His Wife for the First Time

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