HATE TO BREAK IT TO YA with Jamie Kennedy

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HATE TO BREAK IT TO YA with Jamie Kennedy episodes

October 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.
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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.
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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
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SUPPORT THE POD
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1 hr 26 min
October 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.
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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
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🎟️ Tour Dates: https://jamiekennedy.com
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1 hr 46 min
October 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.
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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/
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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.
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Support the Pod:
💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
👕 Merch: jamiekennedy.com/merch
📺 Subscribe: youtube.com/@jamiekennedycomedy

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1 hr 26 min
October 07 From Old Hollywood to Scream: 50 Years of Stories with Joseph Whipp | Ep 278 HTBITY W/ Jamie Kennedy
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.
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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
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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
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SUPPORT THE POD:
💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
👕 Merch: jamiekennedy.com/merch
📺 Subscribe: youtube.com/@jamiekennedycomedy

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1 hr 39 min
September 30 We’re Living in a Matrix… And AI Just Made It Worse | Ep 277 HTBITY with Jamie Kennedy
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.
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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
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Support the Pod:
💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
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50 min
September 23 Mercedes Javid Gets Real About Friendship, Loyalty & Forgiveness | Ep 276 HTBITY w/ Jamie Kennedy
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.
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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
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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
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Support the Pod:
💥 Patreon: patreon.com/thejamiekennedy
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1 hr 20 min
September 16 I Tried One Joke… And the Room Turned on Me | Ep 275 HTBITY with Jamie Kennedy
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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.
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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
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Support the Pod:
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👕 Merch: jamiekennedy.com/merch
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51 min
September 09 The Squatter Hunter on Fake Leases, Broken Laws & Taking Homes Back | Ep 274 HTBITY w/ Jamie Kennedy
This week on Hate To Break It To Ya I sat down with Flash Shelton — better known as The Squatter Hunter — to get inside one of the craziest loopholes in the housing system.
Flash breaks down how squatters and “deceptive tenants” use fake leases, tenant protections and civil law to stay in properties they don’t own — sometimes leaving homeowners stuck fighting for months just to get their own house back. We get into the worst states for it, why police often can’t simply remove someone, some of Flash’s wildest removal tactics, and the cases that pushed him into becoming The Squatter Hunter in the first place.
I also tell Flash about my own experience squatting in Los Feliz when I was a broke actor in the ’90s — and what I discovered after buying a house that had apparently been functioning as a full-blown commune.
Flash also talks about his A&E series Squatters, how his work went viral, and his push to change squatter laws around the country.
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About Flash Shelton:
Flash Shelton is the founder of Squatter Hunters LLC and star and executive producer of A&E’s Squatters. After dealing with squatters in his own family’s property, he began helping homeowners reclaim their homes and has since become one of the most recognizable voices pushing for squatter-law reform.
Follow Flash SheltonInstagram: https://www.instagram.com/flashsheltonX: https://x.com/flash_sheltonYouTube: https://www.youtube.com/@FlashSheltonTikTok: https://www.tiktok.com/@flashsheltonWebsite: https://squatterhunters.com
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Timestamps:
00:00 – How I Met The Squatter Hunter04:50 – How Flash Became The Squatter Hunter19:43 – The Worst States for Squatters28:26 – $130K and a Year to Get Their House Back31:19 – Who Are These Squatters?44:01 – My Own Squatting Story51:41 – The Commune I Found in My House1:00:27 – Flash’s Wildest Squatter Removal Tactics1:05:37 – The Hollywood Hills Squatter Case1:21:00 – Changing Squatter Laws Across America1:25:42 – How to Protect Your Property
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Support the Pod:
💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
👕 Merch: jamiekennedy.com/merch
📺 Subscribe: youtube.com/@jamiekennedycomedy
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Flash Shelton, Squatter Hunter, Hate To Break It To Ya, Jamie Kennedy podcast, squatters A&E show, deceptive tenants, squatter laws United States, homeowner rights, how to remove squatters, squatter hunter 2026, tenant rights loopholes, Flash Shelton interview

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1 hr 31 min
September 02 Panda Express Exposed, WNBA Chaos, & Coca-Cola Bans Jesus | Ep 273 HTBITY w/ Jamie Kennedy
This week I’m back with another Worlds on Fire, and this one starts with restaurant stupidity and somehow ends with Coca-Cola, predictive programming, Apple, the end times and a conversation with Hayden Panettiere that I haven’t talked about before.
I start with one of my biggest restaurant pet peeves: people cleaning around your food while you’re still eating. If the restaurant is open, the kitchen is open — and I definitely don’t need somebody spraying chemicals three feet from my coffee. A Panda Express video sends me over the edge, and it brings back some memories from my own Red Lobster days when I first moved to Los Angeles.
Then things get heavier.
I get into the debate around Sophie Cunningham and women’s sports, why I think people are deliberately making a pretty basic disagreement more complicated than it needs to be, and why labeling somebody a “grifter” because you don’t like their opinion doesn’t actually answer the argument.
From there we get into abortion, the Coca-Cola custom-can controversy, predictive programming, the Twin Towers showing up over and over again in pop culture, and an Apple commercial that sent me down an entirely different rabbit hole. I’m not telling you what to believe. I’m showing you what I’m looking at and asking the same question I keep coming back to:
At what point do enough weird coincidences make you stop and say, “Okay… what the hell is going on?”
And at the end, I wanted to take a few minutes to remember Hayden Panettiere. I didn’t know Hayden well, but we crossed paths through the Scream world, and the last time I saw her at a convention she opened up to me about losing her brother and what she was going through. After hearing about her passing, I haven’t been able to stop thinking about that conversation.
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TIMESTAMPS:
00:00 – The World Is on Fire
02:59 – My Starbucks Hall of Shame
05:02 – Stop Spraying Chemicals Around My Food
09:53 – This Panda Express Video Is Insane
13:43 – Sophie Cunningham & Women’s Sports
21:04 – When Disagreement Becomes a “Grift”
30:03 – Where I Actually Stand on Abortion
39:05 – The Coca-Cola Custom Can Rabbit Hole
47:04 – Predictive Programming & the Twin Towers
49:30 – Apple, 666 & the “Beast System”
53:55 – Are We Living Through Something Bigger?
54:09 – Remembering Hayden Panettiere
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💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
👕 Merch: jamiekennedy.com/merch
📺 Subscribe: youtube.com/@jamiekennedycomedy
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Hate To Break It To Ya, Worlds on Fire, Jamie Kennedy podcast, solo podcast, Sophie Cunningham, women’s sports debate, Coca-Cola custom cans, Jesus Coca-Cola controversy, predictive programming, Apple 666, Apple commercial, Twin Towers predictive programming, Hayden Panettiere, Scream, Scream 6, pop culture conspiracy, current events podcast

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1 hr 1 min
August 26 Scary Movie, Horror Con Chaos & the Real Doofy with Dave Sheridan | Ep 272 HTBITY w/ Jamie Kennedy
This week on Hate To Break It To Ya I sat down with Dave Sheridan — the man behind Officer Doofy and the actual Ghostface killer in the original Scary Movie — and I have to say, this is one of those conversations where I barely had to do anything. Dave just goes. He's one of the few people who genuinely makes me laugh without trying, and this episode is proof of that.
We get into how Dave created Doofy, the strange road that brought him back for Scary Movie 6, and the original $15 vacuum prop that somehow became a piece of movie history. There are also some ridiculous convention stories, including the time that same vacuum helped knock out the power at an entire event in Scotland.
But a lot of this conversation is really about how much the business has changed — auditions, comedy, conventions, making your own projects, and what it takes to keep working when Hollywood doesn’t operate the way it used to. Dave is naturally one of the funniest people I know, so this one goes off the rails pretty quickly.
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About Dave Sheridan:
Dave Sheridan is an American actor, comedian, writer, and producer best known for playing Special Officer Doofy in Scary Movie (2000) — a role he also performed as the physical Ghostface killer throughout the film. He got his start as an SNL intern, trained at The Second City in Chicago, and broke out with the MTV prank series Buzzkill in 1996, which predated Jackass and Tom Green. His other credits include Ghost World (2001), The Devil's Rejects, A Haunted House, A Haunted House 2, and the Glenn Danzig-directed Hellmask. He returned as Doofy and Ghostface in Scary Movie 6, which opened number one worldwide. He is a father of two and one of the most active figures on the horror convention circuit.
Follow Dave Sheridan
Instagram: https://www.instagram.com/davesheridanofficial/
X: https://x.com/DaveSheridan
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00:00:00 – Intro & Catching Up with Dave
00:12:32 – Horror Cons, Skeet Ulrich & How Dave Got Into the Circuit
00:15:26 – The Original Scary Movie Vacuum & the $15 Prop Story
00:30:09 – The Scotland Convention Disaster
00:35:32 – How Dave Became Doofy in Scary Movie
00:43:44 – Hollywood Auditions, Three Kings & Office Space
00:54:39 – Scary Movie, the Wayans & Why Dave Disappeared from the Sequels
01:00:00 – Scary Movie 6, Marlon Wayans & Bringing Doofy Back
01:14:05 – Horror Con Economics, Doofy Dollars & Life on the Circuit
01:30:11 – How Hollywood Auditions Have Changed
01:42:22 – Scary Movie 6 Stories & Making Your Own Movies
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Support the Pod:
💥 Patreon: patreon.com/thejamiekennedy
🎟️ Tour Dates: jamiekennedy.com
👕 Merch: jamiekennedy.com/merch
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Dave Sheridan, Dave Sheridan Scary Movie, Doofy Scary Movie, Scary Movie 6, Marlon Wayans Scary Movie 6, Ghostface actor, horror convention circuit, Jamie Kennedy podcast, Hate To Break It To Ya, Buzzkill MTV, Keenan Ivory Wayans, Dave Sheridan interview 2026

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1 hr 53 min

About HATE TO BREAK IT TO YA with Jamie Kennedy

From the publisher's feed

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.…