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
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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
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On Purpose with Jay Shetty 