HATE TO BREAK IT TO YA with Jamie Kennedy

This week on Hate To Break It To Ya I sat down with Barry Katz — legendary talent manager, producer, and founder of the Boston Comedy Club — and what started as an interview turned into one of the most honest, wide-open conversations I've had on this show. Barry has managed or launched the careers of Dave Chappelle, Bill Burr, Dane Cook, Wanda Sykes, Jay Mohr, Bert Kreischer, Whitney Cummings, Jim Gaffigan, and more than a dozen other names you know by heart. He is, as I told him to his face, the last of a breed — a manager who actually goes to the club, watches the set, and builds the hour alongside the artist. Nobody does that anymore. We got into all of it: what Barry saw in me thirty-two years ago at a Stand-Up New York SNL audition and why he says the Jamie Kennedy on stage today is almost unrecognizable from that kid; the three things that actually make a great stand-up comedian; and why he believes I've been leaving something on the table. That part stung — and I had to sit with it — but he's not wrong. We talked about the 90-10 reality of the manager-artist relationship and why it's structurally set up to end in a firing, how Barry got fired by fax, by FedEx, and in person, and why he'd sign every one of those clients again without hesitation. We went deep on Dane Cook's social media revolution, the Brad Williams YouTube story that changed a comedian's business overnight, and why Barry thinks doubt is the single greatest dream killer working against comedians today. We also got into the Malibu's Most Wanted origin story — Nick Swardson, a spiral notebook, and a fax machine — which is one of the best stories I've heard in years. Barry is one of those rare people who makes you want to go out and destroy. By the end of this conversation I was fired up in a way I wasn't expecting. He's built more careers than anyone I know, he's taken more hits than anyone I know, and he's still smiling. That's the lesson. ⸻⸻⸻⸻⸻ About Barry Katz: Barry Katz is an American talent manager, television and film producer, and the founder of the Boston Comedy Club in New York City, which he ran for seventeen years and which served as the launching pad for some of the most significant careers in modern comedy. Over four decades he has managed or developed Dave Chappelle, Bill Burr, Dane Cook, Wanda Sykes, Jay Mohr, Bert Kreischer, Whitney Cummings, Jim Gaffigan, Darrell Hammond, and many others — selling forty-five out of forty-six comedy specials he has taken to market. He was the executive producer of the Emmy-nominated NBC series Last Comic Standing and has produced Grammy-nominated comedy albums, including Jay Mohr's Happy. And A Lot. He currently hosts the Industry Standard podcast, runs the Blueprint for Success mentorship program for emerging comedians, and continues to manage, produce, and consult across the entertainment industry. Follow Barry Katz Instagram: https://www.instagram.com/barrykatz/ X: https://x.com/BarryKatz Website: https://www.barrykatz.com ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Cold Open & Barry Roasts Jamie's House 00:03:20 – What Barry Saw at the SNL Audition 32 Years Ago 00:09:00 – The Three Things That Make a Great Stand-Up Comedian 00:16:00 – Barry's Honest Take on Jamie's Stage Persona 00:23:00 – Jamie's SNL Audition Story & Life After the Rejection 00:26:00 – Jamie's Career: Auteurs, Roles, and the Town That Changed 00:36:55 – The Gene Simmons Story 00:39:20 – The Dog vs. the Wolf: Barry's Philosophy on Creative Freedom 00:51:20 – The Boston Comedy Club & How Barry Got to New York 00:53:40 – The Client List: 20 Legends and Counting 00:55:50 – Jay Mohr, Addiction, and 30 Years of Partnership 00:58:45 – The 90-10 Truth About the Manager-Artist Relationship 01:03:40 – Barry's Strength Is His Weakness: Doing Everything 01:13:00 – Dane Cook, Social Media, and Changing the Business Forever 01:16:00 – The Brad Williams YouTube Story 01:29:00 – The State of Stand-Up: Too Much Noise or More Opportunity? 01:39:00 – Legacy, Lyrics, and What It Actually Takes to Leave a Mark 01:44:00 – Bombing, Thick Skin, and the Trump Blinders Metaphor 01:53:50 – Kill or Be Killed: The Comedy Store Mentality 02:00:00 – Stock Rising, Stock Falling, and Talent That Never Dies 02:05:50 – The Malibu's Most Wanted Origin Story: Nick Swardson & the Fax Machine 02:10:30 – Closing: Barry Gives Jamie His Flowers ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy ⸻⸻⸻⸻⸻ Barry Katz, Barry Katz podcast, Hate To Break It To Ya, Jamie Kennedy podcast, comedy manager Hollywood, Dave Chappelle manager, Bill Burr manager, Dane Cook social media, Boston Comedy Club, Last Comic Standing producer, Industry Standard podcast, comedy business 2026 Learn more about your ad choices. Visit podcastchoices.com/adchoices

On this weeks episode of Hate To Break It To Ya, I sit down with Andy Dick for one of the rawest conversations we’ve ever had on the podcast. Andy opens up about addiction, relapse, sobriety, and the moment he nearly died—and what it feels like to live under constant scrutiny while trying to stay alive and stay clean. We talk about the early days of comedy in Los Angeles, the chaos of sudden fame, and how addiction distorts memory, responsibility, and relationships. Andy shares his side of long-standing Hollywood controversies, reflects on loss and guilt, and wrestles in real time with what accountability actually means when substance abuse takes over your life. This isn’t a polished redemption story or a hit-piece—it’s an honest, uncomfortable, often funny, and sometimes heartbreaking conversation about losing control, getting sober, and figuring out how to keep going. ⸻⸻⸻⸻⸻ About Andy: Andy Dick is a comedian, actor, and writer best known for his work on NewsRadio, The Ben Stiller Show, and a long run of film and television roles throughout the 1990s and 2000s. A fixture of alternative comedy and Hollywood nightlife during that era, Andy’s career has been marked by both creative success and very public struggles with addiction. In recent years, Andy has been open about sobriety, recovery, and the personal cost of fame, substance abuse, and public scrutiny. His story continues to spark conversation around accountability, addiction, and survival in the entertainment industry. Follow Andy Dick: Instagram: https://instagram.com/@andydick Website: http://www.andydick.com ⸻⸻⸻⸻⸻ Discussed in This Episode: 00:00 – Andy Dick Walks Into Chaos 05:00 – Addiction, Blackouts, and Fuzzy Memory 10:15 – The Crack Incident and Being Narcan’d 16:00 – Surviving, Refusing the Ambulance, and Waking Up 21:00 – Rehab, Sober Living, and the Opioid Crisis 26:15 – Early Comedy Days and the LA Open Mic Scene 31:45 – Fame, Drugs, and Losing Control 36:45 – Sexual Identity, Desire, and Aging 42:30 – Family, Adoption, and Losing His Parents 47:30 – Phil Hartman, Jon Lovitz, and Longstanding Blame 53:45 – Accountability, Survival, and Staying Alive 58:45 – Fame, Perspective, and Closing Thoughts ⸻⸻⸻⸻⸻ Support the Pod 💥 Patreon: patreon.com/thejamiekennedy 🎟 Tour Dates: jamiekennedy.com 👕 Merch: https://jamiekennedy.c... 📺 Subscribe: https://www.youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this solo episode, I break down what’s happening when culture, politics, and reality collide — and why it feels like there’s no middle ground anymore. From media narratives and law enforcement, to Hollywood’s disconnect from real audiences, to the way ideology has replaced common sense, I react to the stories and videos shaping the current moment. I also talk about how fame, legacy media, and award shows are losing relevance, while independent voices and podcasts continue to rise. And at the end, I get personal — about gratitude, aging, health, perspective, and why focusing on what you have matters more than ever. This isn’t about sides. It’s about reality. ________________________________ Timestamps: 00:00:00 Intro & Channel Updates 00:04:16 - Information Overload & Cultural Bubbles 00:08:08 - Tragedy, Free Speech & Public Reaction 00:14:54 - When “Common Sense” Becomes Punk Rock 00:18:21 - Law Enforcement, ICE & Rule of Law 00:27:24 - No Middle Ground Anymore 00:34:25 - Is Hollywood in Decline? 00:42:17 - The Podcast Era & New Power Structures 00:43:06 - Social Media Absurdity & Modern Behavior 00:46:02 - Fear, Health & Modern Anxieties 00:47:28 - Symbolism, Influence & Moral Signals 00:50:31 - Perspective, Gratitude & Life at 55 00:59:35 Final Thoughts ________________________________ Support the Pod 💥 Patreon: patreon.com/thejamiekennedy 🎟 Tour Dates: jamiekennedy.com 👕 Merch: https://jamiekennedy.com/merch/ 📺 Subscribe: YouTube.com/JamieKennedyComedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, I sit down with my buuuuuddy Pauly Shore for an honest, wide-ranging conversation about getting older, looking back, and figuring out what still matters. We talk about fame in the ’90s, the pressure of being Mitzi Shore’s son, how MTV changed the course of his career, and why he still feels pulled toward acting more than comedy. Pauly opens up about regrets, missed opportunities, and what it’s like to be “a thing” while still wanting more. We also get into Hollywood’s shifting rules, being boxed in by success, how critics and politics changed the business, and why reinvention isn’t as simple as people think. It’s funny, raw, reflective — and very real. ⸻⸻⸻⸻⸻ About Pauly: Pauly Shore is a comedian, actor, and cultural icon who rose to fame in the early ’90s through MTV and a run of hit films including Encino Man, Son in Law, In the Army Now, and Bio-Dome. The son of Comedy Store legend Mitzi Shore, Pauly became one of the most recognizable personalities of his generation. Today, he continues touring, creating independent projects, and exploring new chapters in his career. Follow Pauly Shore Instagram: https://instagram.com/@paulyshore Facebook::https://www.facebook.com/OfficialPaulyShore YouTube: https://www.youtube.com/c/paulyshore/ Website: http://www.paulyshore.com ⸻⸻⸻⸻⸻ Discussed in This Episode 00:00 — “We’re in Our 50s… How Did This Happen?” 01:01 — “The Scan That Changed Everything” 15:56 — “Before MTV: Acting, Auditions, and the Other Path” 18:08 — “The Fork in the Road That Defined My Career” 22:47 — “Being a ‘Thing’ vs Being Respected” 26:23 — “MTV Didn’t Believe in Me — Until It Was Too Late” 41:38 — “What Fame Took That No One Talks About” 45:59 — “The Comedy Store Pressure Nobody Sees” 58:24 — “Why I Actually Love Acting More Than Comedy” 01:05:04 — “Still Chasing the Second Act” ⸻⸻⸻⸻⸻ Support the Pod 💥 Patreon: patreon.com/thejamiekennedy 🎟 Tour Dates: jamiekennedy.com 👕 Merch: https://jamiekennedy.c... 📺 Subscribe: https://www.youtube.com/@jamiekennedycomedy _________________________________ Pauly Shore podcast, Pauly Shore interview, MTV 90s comedy, Mitzi Shore, Comedy Store history, 90s Hollywood, comedian career regrets, Pauly Shore acting, Jamie Kennedy podcast, Hollywood reinvention Learn more about your ad choices. Visit podcastchoices.com/adchoices