HATE TO BREAK IT TO YA with Jamie Kennedy

Hate To Break It To Ya with Jamie Kennedy
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He’s mad as hell and he’s not going to take it anymore. HATE TO BREAK IT TO YA is a weekly podcast hosted by actor/comedian Jamie Kennedy. Jamie is on a constant quest to get to the bottom of things. Step inside Jamie’s brain where you will be confronted with idea’s that are unique and thought-provoking. An assault on your ears with a spin you may not want to hear.... Support this podcast: https://podcasters.spotify.com/pod/show/jamie-kennedy0/support

  1. 6D AGO

    Comedy, Criticism, and Being a Good Guy While Playing the Villain with Jeff Dye | Ep 239 HTBITY

    Jeff Dye sits down with me for a wide-ranging conversation about ambition, conviction, and what it actually means to stay true to yourself in modern comedy. We talk about why Jeff believes his goal is to be the best stand-up comedian possible, how that mindset shapes his choices, and what it’s like being perceived as the “bad guy” while still leading with honesty and goodwill. We also get into navigating public pressure, playing the heel intentionally, and why comedy sometimes eats its own — all without turning this into a pile-on or a hit piece. This is a thoughtful, candid conversation about identity, craft, and surviving the long game. ⸻⸻⸻⸻⸻ About Jeff Dye: Jeff Dye is a nationally touring stand-up comedian, actor, and host. He’s appeared multiple times on The Tonight Show with Jimmy Fallon, has his own Comedy Central Presents special, and has released two top-10 Billboard comedy albums, Dumb Is Gooder and Live From Madison, both currently playing on SiriusXM. He’s starred in NBC’s Better Late Than Never, appears regularly on Fox shows like The Masked Singer and I Can See Your Voice, and hosts the Fox game show Who the Bleep Is That?. Jeff is also a recurring guest on The Greg Gutfeld Show, known for delivering unfiltered takes with humor, conviction, and heart. Follow Jeff: Instagram: https://instagram.com/@jeffdye YouTube: https://www.youtube.com/c/jeffdye/ Website: http://www.jeffdye.com ⸻⸻⸻⸻⸻ Discussed in This Episode: 00:00 – Comedy convictions 03:45 – Clean vs edgy comedy 07:30 – Losing the filter 12:10 – Public pressure 17:55 – Sobriety & accountability 22:40 – Privacy vs publicity 27:30 – Wanting to be the best 31:45 – Texas, touring & home 36:30 – Playing the heel 41:50 – Comics turning on comics 47:20 – Forgiveness over revenge 53:10 – Being likable, staying honest 59:00 – The long game 01:05:30 – Final 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

    1h 14m

  2. JAN 5

    Pauly Shore Opens Up About Success, Regret, and Reinvention

    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

    1h 8m

  3. 12/29/2025

    Beverly D’Angelo on Love, Fame, and the Life That Happened in Between | Ep 237 HTBITY with Jamie Kennedy

    In this episode, I sit down with the legendary Beverly D’Angelo for a wide-ranging and deeply personal conversation about love, independence, and the unexpected paths life can take. Beverly opens up about leaving home at a young age, living abroad, navigating unconventional relationships, and how much of her real life unfolded far away from Hollywood. We talk about emotional memory, trauma, and how early experiences can shape the way we connect, protect ourselves, and move through the world. Beverly reflects on her career, her personal growth, and why the stories that happen off screen often matter more than the roles we play on it. This is an honest, thoughtful conversation with an iconic actress who’s lived a truly unique life — full of insight, humor, and perspective you don’t often hear. Beverly D’Angelo is an actress and singer best known for her iconic roles in National Lampoon’s Vacation, Coal Miner’s Daughter, and countless film and television projects spanning decades. With a career rooted in both performance and music, Beverly has remained a distinctive voice in Hollywood, known for her depth, authenticity, and fearless honesty. About Beverly: Beverly D’Angelo is an actress and singer best known for her iconic roles in National Lampoon’s Vacation, Coal Miner’s Daughter, and countless film and television projects spanning decades. With a career rooted in both performance and music, Beverly has remained a distinctive voice in Hollywood, known for her depth, authenticity, and fearless honesty. Learn more about your ad choices. Visit podcastchoices.com/adchoices

    1h 36m

  4. 12/23/2025

    Truth, Grief, and the Feeling That Something’s Ending | Ep 236 HTBITY w/ Jamie Kennedy

    In this solo episode, I talk through why the world feels different, why empathy seems to be disappearing, and why so many things we’ve normalized just don’t sit right anymore. From censorship and cultural numbness to grief, excess, masculinity, escapism, and the loss of innocence, this episode is about recognizing the shift we’re all feeling but rarely say out loud. I also reflect on burnout, pulling back from overexposure, and what it means to evolve without retreating into denial. There’s frustration here, but there’s also clarity — about protecting what matters, shedding old versions of ourselves, and staying human in a world that often feels upside down. ________________________________ 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

    52 min

  5. 12/15/2025

    Capitol Chaos, Surviving Prison, and Getting Pardoned with Jon Mellis | Ep 235 HTBITY

    In this episode, I sit down with Jon Mellis, whose life story spans a decade in state prison, years of rebuilding on the outside, and ultimately his presence at January 6th. Jon walks through his early drug conviction, the realities of incarceration, how prison reshaped his worldview, and what it’s like to reenter society after losing nearly all of your twenties behind bars. We also get into Jon’s political evolution — from being a Bernie supporter to becoming deeply skeptical of institutions, media narratives, and government power — and his firsthand account of January 6th, including what he says he witnessed, how he was arrested, and the years he spent in solitary confinement afterward. Whether you agree or disagree, this is a long-form conversation about how systems break people, and what happens when pressure builds for too long. About Jon Mellis Jon Mellis is a Virginia native who served nearly ten years in state prison on drug-related charges before rebuilding his life through work, volunteering, and education. After becoming politically active in the years following his release, Jon was later arrested in connection with January 6th and spent years in pretrial detention. His story offers a firsthand perspective on incarceration, institutional power, and political radicalization from the inside out. Follow Jon: Instagram: https://instagram.com/patriotwildman Website: https://wearegoodmen.com Management: https://www.instagram.com/michellefarrellmanagement ______________________________________________ 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

    1h 27m

  6. 12/08/2025

    Are We All Being Played? Comedy, Politics, Sports & The Illusion of Control | Ep 234 Hate To Break It To Ya with Jamie Kennedy

    In this episode I’m talking about everything from my new movie Portal in the Pines to why it feels like the whole world is running on glitch mode. I break down that insane NFL penalty everyone’s been sending me, and yeah… I’m starting to think some of these games aren’t as “pure” as we were told. We also get into old-school Hollywood, Gallagher, Chevy, Carson — a bunch of legends — and how different the world feels now compared to the stuff I grew up watching. There’s a clip about comedians “not being truth tellers,” which I definitely have thoughts on, plus a Wizard of Oz theory that completely melted my brain. If you’re into comedy, movies, weird clips from the internet, or just trying to make sense of the chaos out there, come hang for a bit. ______________________________________________ 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

    52 min

  7. 12/01/2025

    Peter Madrigal on Vanderpump Secrets, Reality TV Chaos & Hollywood Today | Ep 233 HTBITY with Jamie Kennedy

    Peter Madrigal stopped by the studio and we got into the real story behind his time on Vanderpump Rules, the early days at SUR, and what it was like being part of one of the biggest reality TV shows of the last decade. We talk about how the show started, how the cast handled real relationships on camera, the behind-the-scenes work that goes into filming, and how Peter managed the chaos both on and off screen. We also get into the Scandoval fallout, the rise of reality TV stardom, and where the entire genre is heading as Hollywood keeps shifting. Peter also opens up about building his own network, life after reality fame, and how he sees the future of entertainment. About Peter: Peter Madrigal is a television personality, producer, and longtime cast member of Vanderpump Rules, appearing in ten seasons of the hit Bravo series. Known for his role as manager at SUR Restaurant, Peter has also moved into directing and producing his own projects, including his growing Reality Network on Roku. Outside of TV, Peter has been active in the nightlife and hospitality world and has launched the PM Coin project aimed at the future of digital payments. Follow Peter Madrigal: Instagram: https://instagram.com/peter_madrigal TikTok: https://www.tiktok.com/@peter_madrigal/ Reality Network: https://realitynetworktv PM Coin: https://pmcoin.xyz ________________ Join me on Patreon for bonus content and early episodes: https://www.patreon.com/thejamiekennedy Tour Dates and Tickets: https://www.jamiekennedy.com Merch: https://www.jamiekennedy.com/merch Subscribe for more clips and full episodes Learn more about your ad choices. Visit podcastchoices.com/adchoices

    1h 9m

  8. 11/24/2025

    Street Madness, Demon Bee Discovery, and Social Media Delusion | Ep 232 HTBITY with Jamie Kennedy

    I’m back with a new solo episode, and the world feels like it’s getting stranger by the day. From bizarre street behavior in Studio City to demon bees in Australia, to airports charging seventeen bucks for pistachios, I’m starting to wonder if something bigger is going on. I dive into why everything feels upside down, how comedy has changed, why real people online are funnier than Hollywood right now, and why everyone suddenly thinks they’re a comedian. We also get into conspiracy talk, UFO theories, demons, nostalgia, and the lost art of originality. This one is all over the map in the best way. Think wild viral clips from my FYP, memories from the golden era of stand up, bizarre real-world moments, and some big questions about where society is heading. Grab a coffee and hang with me. ___________________________ Timestamps: 01:16 – Beauty pageant performs metal 02:55 – Local news segment about the man causing chaos in Studio City 10:54 – Australian “demon bee” news report 17:30 – Vintage stand-up bit from Mr. Zed 24:36 – Food review video from Chris & Eddie’s 29:02 – Rant clip about “white people that triple trapped” with Michael Malice 31:04 – Sixteen Candles scene with Jake / Caroline / Anthony Michael Hall 39:26 – Burbank airport nuts rant ___________________________ For more information on the National AC refrigerant crisis, how it will affect homeowners, and how to SIGN THE PETITION please visit: http://www.MAACAA.ORG ___________________________ Follow Me: Website: https://jamiekennedy.comInstagram: https://instagram.com/thejamiekennedyFacebook: https://facebook.com/jamiekennedyTikTok: https://tiktok.com/@thejamiekennedyTwitter/X: https://x.com/jamiekennedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

    46 min
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4.8
out of 5
189 Ratings

About

He’s mad as hell and he’s not going to take it anymore. HATE TO BREAK IT TO YA is a weekly podcast hosted by actor/comedian Jamie Kennedy. Jamie is on a constant quest to get to the bottom of things. Step inside Jamie’s brain where you will be confronted with idea’s that are unique and thought-provoking. An assault on your ears with a spin you may not want to hear.... Support this podcast: https://podcasters.spotify.com/pod/show/jamie-kennedy0/support

Information

  • Creator
    Hate To Break It To Ya with Jamie Kennedy
  • Years Active
    2017 - 2026
  • Episodes
    243
  • Rating
    Explicit
  • Copyright
    © Hate To Break It To Ya with Jamie Kennedy
  • Show Website
    HATE TO BREAK IT TO YA with Jamie Kennedy

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