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: https://www.instagram.com/jimmykimmel/ https://www.facebook.com/jimmykimmel/ https://www.youtube.com/user/JimmyKimmelLive https://x.com/jimmykimmel https://www.tiktok.com/@jimmykimmellive https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me