Jay Shetty Podcast

Jimmy Kimmel REVEALS: I Got Fired So Many Times Because of My Behavior..

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

JKJimmy KimmelguestJSJay Shettyhost

Aug 13, 2025·51m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Live at The Greek: playful roast sets the tone

   Jay Shetty welcomes Jimmy Kimmel onstage at The Greek Theatre, and Jimmy immediately flips the script with quick-fire jokes and crowd banter. The opening establishes their chemistry: affectionate roasting, improvisation, and a relaxed, live-show energy.

2. 2

   Why putting yourself out there feels risky (and why people hold back)

   Jimmy reflects on how self-consciousness shows up in everyday situations—like being underdressed—and how fear of failing in public keeps people from pursuing their talents. He explains how radio helped him take “baby steps” into visibility before bigger career leaps.

3. 3

   Childhood creativity and the real origin story: artist, not scientist

   Jay asks about Jimmy’s early ambitions, and Jimmy corrects the record: he wanted to be an artist. He describes drawing classmates, caricatures, and even sketching David Letterman while watching TV—habits he still keeps today.

4. 4

   The prank instinct: family reactions, Aunt Chippy, and escalating chaos

   Jimmy explains why he loves pranks: big reactions were rewarded in his loud, expressive family. He shares long-running antics with Aunt Chippy—culminating in a high-production self-driving car prank—showing how mischief became a signature comedic language.

5. 5

   Getting fired again and again: when the pranks hit the bosses

   Before TV resources, Jimmy’s pranks at radio stations often targeted managers—and repeatedly cost him jobs. He recounts specific incidents (golf clubs, the “hot dog in the desk” saga) and admits that what felt funny to him read as antisocial in a workplace.

6. 6

   The emotional toll of firing and being fired (and learning restraint)

   Jimmy describes the blunt reality of being fired, including being escorted out with a box and the fear of telling his family. The experiences later shaped him into a boss who finds firing people painful and who learned to temper impulsive behavior.

7. 7

   Staying true to a creative voice: ‘pure delusion’ and trusting your taste

   Pressed on how he persisted despite rejection, Jimmy credits ‘pure delusion’—and also self-awareness about not always being good early on. He shares how trusting what he finds funny helped him spot talent in others and turn family “annoyances” into audience favorites.

8. 8

   Becoming a grandfather: pride, weirdness, and ‘revenge’ parenting

   Jimmy celebrates his newborn granddaughter and describes the surreal feeling of watching his daughter become a mother. He jokes about grandparenthood as a chance to break the rules his kids will set—continuing the family’s comedic spirit.

9. 9

   Living with anxiety: scarcity, habits, and how it shows up in family life

   Jimmy opens up about anxiety as something he didn’t want his kids to inherit, shaped partly by growing up without money. He illustrates anxiety through small, vivid behaviors—like saving art pens until they dried out—and how he now overcompensates by hoarding supplies.

10. 10

    Financial pressure when success arrives: being the one everyone asks

    Jimmy contrasts the simplicity of money anxiety when broke with the complexity of wealth and responsibility. He describes how relationships shift when people rely on you, and the challenge of handling requests—especially when money reveals misaligned priorities.

11. 11

    Love story and marriage ‘check-ins’: how Molly helped him grow

    Jimmy shares how he met his wife Molly on his show and credits her with helping him mature emotionally. Their playful couples-therapy vibe reveals a core truth: she brings emotional fluency and outward compassion that balances his tunnel vision and deflection humor.

12. 12

    Why feelings are hard to talk about: therapy, listening, and helping others

    Jimmy says emotional expression is challenging, likely learned from family modeling, though writing is easier than speaking. He endorses therapy (individual and couples) and offers a practical pathway for low moments: help someone else to break self-focus and restore worth.

13. 13

    Final Five + rapid reflections: rules to live by and future hopes

    Jay closes with the show’s “Final Five,” where Jimmy offers quick, values-driven answers—plus humor. He ends with the Golden Rule as his universal law and hopes to be remembered like his grandfather: loved and thought of fondly.