HATE TO BREAK IT TO YA with Jamie Kennedy

Hate To Break It To Ya with Jamie Kennedy
  • 4.3 (6)
  • News Commentary
  • Weekly

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. 1d ago

    Hefner Parties, Beauty Pageants & Hollywood's Wild Side with Shanna Moakler | Ep 282 HTBITY

    Shanna Moakler has seen just about every side of Hollywood. From becoming Miss USA and a Playboy Playmate to her relationships with Travis Barker and Oscar De La Hoya, she's got stories most people have only read about in tabloids. We get into her dispute with Donald Trump over the Miss USA organization, how beauty pageants have changed, and what it was really like spending time with Hugh Hefner at the Playboy Mansion. Shanna opens up about her marriages, raising children in the public eye, and finding happiness in her 50s. She also shares her perspective on the controversies surrounding Hefner, her women's wellness business, and her surprisingly elaborate preparations for a zombie apocalypse. We also go down some wild Hollywood rabbit holes, including Britney Spears conspiracy theories, the Lindsay Clancy case, and Shanna's firsthand memories of attending Diddy's famous White Parties. It's a conversation about celebrity culture, relationships, old Hollywood, and how much the entertainment industry has changed. ⸻⸻⸻⸻⸻ About Shanna Moakler: Shanna Moakler is an actress, model, entrepreneur, and former Miss USA 1995, best known for her appearances on MTV's Meet the Barkers and the television series Pacific Blue. She was named Playboy's Playmate of the Month in December 2001 and has spent more than a decade working in the beauty pageant industry, including leadership roles with Miss Nevada USA and Miss Utah USA. A mother of three, Shanna continues to work in entertainment, production, and women's wellness through her various business ventures. Follow Shanna Moakler: Instagram: https://www.instagram.com/shannamoakler/ X: https://x.com/ShannaMoakler Official Website: https://shannamoakler.com/ ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Shanna Moakler: Miss USA, Hollywood, and Life in the Spotlight 00:10:56 – Donald Trump, the Miss USA Controversy, and Shanna's Resignation 00:14:00 – Transgender Contestants, Beauty Pageants, and Changing Standards 00:26:45 – Hugh Hefner and Life Inside the Playboy Mansion 00:33:00 – The Hugh Hefner Allegations and Playboy Mansion Documentaries 00:43:05 – Travis Barker, Oscar De La Hoya, and Celebrity Relationships 00:54:45 – Women's Wellness, Aging, and Finding Happiness After 50 00:58:10 – Shanna Moakler's Zombie Apocalypse Survival Plan 01:01:55 – The Lindsay Clancy Case and Celebrity Conspiracy Theories 01:09:50 – Diddy's White Parties and the Wild Days of Hollywood Nightlife ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  2. Oct 28

    Inside O.J. Simpson's Controversial Show & the New Documentary with Todd Lewis | Ep 281 HTBITY

    This week on Hate To Break It To Ya, I'm sitting down with Todd Lewis, the guy who directed O.J. Simpson's infamous hidden-camera prank project, Juiced, and helped bring the story back into the spotlight through the new Investigation Discovery documentary, O.J. Unseen: Exploitation of Evil. Todd was actually there, working with O.J. during one of the strangest attempted comebacks in entertainment history. We get into how the project came together, what O.J. was really like behind the cameras, the footage that caused controversy, and why Todd disagrees with parts of the documentary's portrayal of what happened. We also go down the rabbit hole of the O.J. Simpson murder case, including alternative theories Todd has explored over the years. Then we get into the wild early days of reality television, the strange stories behind Trick My Truck, and what it's like being Jeff Lewis's brother in the world of Bravo and Chump Land. This one brings me right back to the era of The Jamie Kennedy Experiment, Punk'd, Jackass, and a time when Hollywood was willing to take some truly insane chances. ⸻⸻⸻⸻⸻ About Todd: Todd Lewis is a television producer, director, and entertainment industry veteran whose work spans reality television, hidden-camera comedy, and documentary development. He directed O.J. Simpson's controversial prank project Juiced and served as a consulting producer on O.J. Unseen: Exploitation of Evil. His television background also includes Trick My Truck, and he's the brother of Bravo and SiriusXM personality Jeff Lewis. ⸻⸻⸻⸻⸻ Timestamps: 00:00 – Todd Lewis, O.J. Simpson & the New Documentary 07:46 – The Wild Early Days of Reality TV and Viral Videos 15:39 – What O.J. Simpson Was Really Like on Set 22:52 – The Leaked Footage That Derailed O.J.'s Comeback 28:00 – Todd's On-Set Confrontation with O.J. 32:58 – Did Todd Try to Get a Confession from O.J.? 39:23 – Alternative Theories About the O.J. Simpson Murders 47:01 – The Bronco Chase and the Birth of Reality TV 53:14 – What Todd Disagrees With in the Documentary 1:05:48 – The Strange Stories Behind Trick My Truck 1:12:14 – Jeff Lewis, Bravo & the Changing Television Business 1:19:06 – Jeff Lewis's Success, SiriusXM & Chump Land ⸻⸻⸻⸻⸻ SUPPORT THE POD 💥 Patreon: https://patreon.com/thejamiekennedy 🎟️ Tour Dates: https://jamiekennedy.com 👕 Merch: https://jamiekennedy.com/merch 📺 Subscribe: https://youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  3. Oct 21

    The Comedy Police Are Losing Their Minds | Ep 280 HTBITY w/ Jamie Kennedy

    Everybody has an opinion about comedy these days, but does anybody actually understand it anymore? In this solo episode of Hate To Break It To Ya, I'm getting into the growing epidemic of people who think having a social media following makes them an expert on everything, especially stand-up comedy. From influencers to fellow comedians, it seems like everyone's trying to police what can and can't be funny. And frankly, I'm tired of it. First, I'm breaking down the Raw Dog Radio controversy involving Sebastian Maniscalco, SiriusXM, and hundreds of comedians who were removed from the channel. I share my own experience with The Jamie Kennedy Experiment and how a decision to take the show to ABC Family instead of Comedy Central may have cost me $25 million in potential royalties. That's show business. Nobody owes you anything, and sometimes you have to adapt. Then there's Pete Davidson calling out influencers making millions from social media, and the backlash he received. What happened to earning your place in entertainment? What's the difference between having followers and leaving behind an actual legacy? I react to the response and explain why I think Pete has a point. Finally, we get into the Shane Gillis SNL controversy. I break down his joke, explain why I think people completely missed the punchline, and react to the comedians, doctors, and online critics calling it offensive. I also get into Dan Levy's response, Aries Spears' take, and why comedians criticizing other comedians has become such a problem. We've lost our collective minds. It's time to bring back some sanity. ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Nobody Understands Comedy Anymore 00:08:27 – Comedians Policing Comedians & the Shane Gillis Backlash 00:20:34 – Sebastian Maniscalco & the Raw Dog Radio Controversy 00:24:07 – How The Jamie Kennedy Experiment Cost Me $25 Million 00:41:36 – Pete Davidson vs. Influencers: Fame, Money & Legacy 01:04:03 – Dollhouse of Dread: Ghost Face, Pinhead & Jason at Walmart 01:07:49 – Breaking Down Shane Gillis' Controversial SNL Joke 01:16:51 – Aries Spears Defends Shane Gillis 01:30:13 – Doctors, Comedy Critics & the Outrage Over Jokes 01:43:36 – We've Lost Our Minds: Bring Back Sanity ⸻⸻⸻⸻⸻ 💥 Patreon: https://patreon.com/thejamiekennedy 🎟️ Tour Dates: https://jamiekennedy.com 👕 Merch: https://jamiekennedy.com/merch 📺 Subscribe: https://youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  4. Oct 14

    Anthony Michael Hall on John Hughes, the Brat Pack & Getting Fired From SNL | Ep 279 HTBITY

    Anthony Michael Hall is one of those actors whose movies helped define an entire generation. This week on Hate To Break It To Ya, I finally got to sit down with someone I've admired since I was a kid. The Breakfast Club was one of the movies that made me want to become an actor, so getting to hear these stories firsthand was pretty incredible. We get into his early days working with John Hughes on The Breakfast Club, Sixteen Candles, and Weird Science, including the iconic moments he improvised on set. Anthony shares stories about his relationships with Hollywood legends, his experience working with Tim Burton and Christopher Nolan, and how he went from being one of the biggest teenage stars in the world to joining Saturday Night Live at just 17 years old. We also talk about the Brat Pack, getting fired from Taps before Tom Cruise landed the role, his friendship with Robert Downey Jr., and why even after 51 years in Hollywood, he's still auditioning for parts. From the wild days of SNL to The Dark Knight, Reacher, and everything in between, Anthony has seen just about every side of this business. This was a really special conversation for me, and I hope you enjoy it. ⸻⸻⸻⸻⸻ About Anthony Michael Hall: Anthony Michael Hall is an actor, producer, and director best known for his iconic roles in John Hughes classics Sixteen Candles, The Breakfast Club, and Weird Science. At 17, he became the youngest cast member in Saturday Night Live history. His extensive career also includes Edward Scissorhands, Pirates of Silicon Valley, The Dead Zone, The Dark Knight, Halloween Kills, and Reacher. Follow Anthony Michael Hall: Instagram: https://www.instagram.com/amh4real/ ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Anthony Michael Hall Joins the Podcast 00:03:05 – How The Breakfast Club Changed My Life 00:09:01 – Edward Scissorhands, Tim Burton & Reinventing Himself 00:14:19 – John Hughes and the Freedom to Improvise 00:21:23 – Hollywood Auditions, Christopher Nolan & Halloween Kills 00:29:30 – How Hollywood and the Entertainment Industry Changed 00:39:51 – The Brat Pack, Molly Ringwald & Tom Cruise 00:48:13 – Reality TV, Alec Baldwin & Ice-T 00:53:52 – Behind the Scenes of Weird Science 01:03:32 – Reacher, Hollywood & What's Next 01:14:32 – Joining Saturday Night Live at Just 17 01:20:16 – Getting Let Go from SNL with Robert Downey Jr. ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  5. Oct 7

    From Old Hollywood to Scream: 50 Years of Stories with Joseph Whipp

    This week I sat down with Joseph Whipp, who played Sheriff Burke in the original Scream and Sergeant Parker in A Nightmare on Elm Street, and I realized pretty quickly how much of his story I had never heard. Long before Scream, Joseph was a high school drama teacher in Northern California and spent two and a half years playing Randall P. McMurphy in a San Francisco production of One Flew Over the Cuckoo’s Nest before Jack Nicholson took the role to the screen. We get into those early theater years, old-school Hollywood, working with Wes Craven, Cheers, The Golden Girls, Sean Connery, Karl Malden, Paul Sorvino, Johnny Depp and a completely different era of being a working actor. We also go back through Scream, why Sheriff Burke was never actually killed, why Joseph still thinks they could have brought him back, the insanity of the horror convention circuit, and his ongoing plan for the inevitable Scream 59. I’ve known Joseph for years from the Scream convention world, but I genuinely got to know him during this conversation. At 85, he’s still hilarious, sharp, full of stories and has more than five decades of Hollywood history behind him. ⸻⸻⸻⸻⸻ About Joseph Whipp: Joseph Whipp is an actor whose career spans more than five decades. He is best known to horror fans as Sheriff Burke in Scream and Sergeant Parker in A Nightmare on Elm Street. His credits also include Escape from Alcatraz, Cheers, The Golden Girls, Generations, Death Spa, The Hidden and Wrong Is Right. Before his screen career, Joseph taught drama at Carlmont High School and spent two and a half years performing Randall P. McMurphy in a San Francisco production of One Flew Over the Cuckoo’s Nest. Follo Joseph Whipp: Website: josephdwhipp.com Instagram: @josephdwhipp ⸻⸻⸻⸻⸻ TIMESTAMPS: 00:00:00 – The Scream 59 Origin Story 00:07:57 – From San Francisco to Venice Beach 00:17:50 – Playing McMurphy Before Jack Nicholson 00:28:00 – Sheriff Burke Never Got Killed 00:41:00 – The Biggest Scream Convention Jamie Ever Did 00:49:50 – Hollywood in the ’80s & Creative Friction 00:57:00 – The Cheers Audition With One Hour’s Notice 01:10:00 – Johnny Depp, Wes Craven & Betty White 01:23:00 – Wild Stories From the Horror Convention Circuit 01:33:00 – The Scream Family & Scream 59 ⸻⸻⸻⸻⸻ SUPPORT THE POD: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  6. Sep 30

    We’re Living in a Matrix… And AI Just Made It Worse

    This week I’m going down the AI rabbit hole because something about this story is getting seriously weird. An AI researcher leaves Anthropic warning about how dangerous this technology could become, we're hearing claims about rogue bots escaping their sandbox, hacking systems and even leaving self-replicating code around the internet — and I’m trying to figure out how much of this is real and how much could be a work. Right now I’m about 75/25. I think something very real is happening with AI, but I also have questions about why we're suddenly being flooded with warnings, who benefits from regulation, and whether fear could be used to lock down the industry. Either way, I think 2027 is going to look very different. Save the tape. I also explain why I’m convinced we live in some kind of matrix after connecting O.J. Simpson, the Bronco chase, MTV, the Kardashians, Jeff Lewis and my own prank-show history. Then we get into some absolutely insane clips from Los Angeles and Portland, the Sydney Sweeney debate, and finally a “greatest TV shows” list that has me asking how some of the biggest shows in pop culture somehow didn’t make the cut. ______________________ Timestamps: 00:00:00 – Trejo’s Donuts, Life Updates & Full Transparency 00:05:50 – The O.J.-Kardashian-Prank Show Matrix 00:10:32 – Is AI Getting Out of Control? 00:14:43 – The AI Whistleblower: Real or a Work? 00:20:55 – Rogue AI, Regulation & Self-Replicating Code 00:28:31 – My 2027 Prediction: Save This Tape 00:32:21 – The Portland Chromosome Shirt Controversy 00:39:07 – The Sydney Sweeney Debate 00:43:37 – The “Best TV Since 2000” List Makes No Sense ______________________ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  7. Sep 23

    Mercedes Javid Gets Real About Friendship, Loyalty & Forgiveness

    This week on Hate To Break It To Ya I sat down with Mercedes “MJ” Javid, and we had a lot to catch up on. We get into the world of Jeff Lewis and Chump Land, what happens when people fall out of a friend group, loyalty, getting “de-chumped,” and why some people walk away gracefully while others burn everything down on the way out. MJ also opens up about someone dropping dime on her during the first Chump Con, and then we finally get into our own beef. We break down what happened between us on camera, where things went wrong, and why she believes being able to apologize, forgive and move forward is healthier than hanging onto resentment. We also talk about the early days of reality TV and Bravo, Shahs of Sunset, her real estate career, my ridiculous house hunt, where the whole Jeff Lewis universe is headed, and the new chapter she’s building for herself. MJ and I can argue, laugh, go completely off the rails and somehow land on something real by the end of it. This was one of those conversations. ⸻⸻⸻⸻⸻ About Mercedes “MJ” Javid: Mercedes “MJ” Javid is a television personality and luxury real estate broker best known as an original cast member of Bravo’s Shahs of Sunset. She returned to the Bravo world with The Valley: Persian Style and is also entering a new chapter with her upcoming solo podcast, New Season. Follow MJ: Instagram: https://www.instagram.com/mercedesjavid/ X: https://x.com/MercedesJavid ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – MJ Does Her Makeup Live & The Cartier Bracelet Story 00:07:08 – How People Exit Friend Groups: Grace vs. Scorched Earth 00:12:55 – The Chump Con Incident: Someone Dropped Dime on MJ 00:20:11 – How MJ First Got Into Jeff's World & Their History on the Show 00:25:08 – Jamie and MJ's On-Air Beef: What Really Happened 00:39:47 – OG Bravo Wives, Paris Hilton, and the Birth of Reality TV 00:43:02 – The Apology: MJ Says Sorry and Means It 00:54:55 – Forgiveness Is Health 01:02:26 – The House Hunt: Elevator Houses, Freeway Studios & Finding Home 01:09:01 – Where Is Chump Land Headed? Jeff, Howard Stern, and the Future ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

  8. Sep 16

    I Tried One Joke… And the Room Turned on Me

    Your house. Your family. Your peace of mind. Protect it with my sponsor SimpliSafe. Get 50% off your system at https://simplisafe.com/jamiekennedy. There’s No Safe Like SimpliSafe. ✅ ⸻⸻⸻⸻⸻ Back with another solo episode, and this one happened because I came home from the Laugh Factory way too fired up to go to sleep. I went up on a Monday night, the set was going great, and then I tried one joke that completely changed the room. People started arguing, people started walking out, and at one point I actually offered an audience member $100 to leave. They didn't take it. So I wanted to sit down and talk through what happened, why the joke hit such a nerve, and where comedy is right now when a room can go from laughing together to completely divided in a matter of seconds. I also get into what happened after the show, the conversation I had with the person I offended, and why I still think comedy has to be a place where we're allowed to push things, get uncomfortable, disagree, and hopefully still laugh. This one got weird fast. ⸻⸻⸻⸻⸻ TIMESTAMPS: 00:00 – I Just Got Back From the Laugh Factory 03:16 – The Set Was Going Great… Until It Wasn’t 07:48 – The Joke That Changed the Room 13:24 – I Offered an Audience Member $100 to Leave 20:56 – I Apologized, Hugged It Out… And She Still Wasn’t Happy 27:03 – Can We Still Joke About Everything? 31:25 – Watching the Actual Footage From the Show 37:44 – The Apology, the Hug & What Happened Next 46:10 – Final Thoughts on the Night ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Ratings & Reviews

4.3
out of 5
6 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
    2025 - 2026
  • Episodes
    286
  • Rating
    Explicit
  • Copyright
    © Hate To Break It To Ya with Jamie Kennedy

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