Stu Stone on the New Hollywood Hustle and the Rolling with Saget Years| Ep 265 HTBITY

This week on Hate To Break It To Ya I sat down with Stu Stone — actor, filmmaker, rapper, podcast pioneer, and one of my oldest friends in this business — for a conversation that was 25 years in the making. Stu has been on this couch more than anyone else, which tells you everything you need to know about the quality of what he brings. We went deep on the era that defined both of our careers, the hustle that got us there, and the economy that's keeping us alive today. We covered a lot of ground. We got into how the convention circuit has quietly become one of the most reliable income streams in Hollywood — Eli Roth called it "the new residuals" and he is not wrong. We talked about Tremors 5 selling 863,000 DVDs, residual checks from Enemy of the State, and why getting on Netflix might actually be the worst financial move you can make. Then we went back to the origin story of "Rolling with Saget" — the song that started as a demo recorded in a porn warehouse in the Valley for $40 an hour, almost starred Jeff Goldblum, got passed on by every rapper in the game (including Akon, which we will always regret), and then went to number one on MySpace overnight. We watched footage from the MTV show Blowing Up, including a clip of Bob Saget rapping in the Hummer on Sunset, and we talked about the meeting at Warner Brothers where we had to explain the concept to the chairman of the label by singing "Boogie in Your Butt." We also got into how I created a fake manager named Marty Power — a cross between Robbie Benson and James Woods — to get my first auditions, and how selling sandwiches to Barry from Barry's Boot Camp was the beginning of learning how to sell myself. Stu is one of the few people who has been there for every version of me — Lexus Jamie, Hummer Jamie, Bentley Jamie, pandemic Jamie — and watching these old clips together reminded me how much we actually built from nothing. This one goes long and it earns every minute. ⸻⸻⸻⸻⸻ About Stu Stone: Stu Stone (born Stuart Eisenstein) is a Canadian actor, filmmaker, rapper, and producer who has been working in the entertainment industry since age two. He is best known for playing Ronald Fisher in Donnie Darko, voicing Ralphie Tennelli on The Magic School Bus, and co-starring with Jamie Kennedy in the 2006 MTV reality series Blowin' Up. He is a director and co-founder of 5'7 Films, whose horror feature The Haunted House on Kirby Road won Best Horror Feature at the Toronto Independent Film Festival. His current projects include the film Don't Mess with Ghosts, a re-release of Faking a Murderer, and Dark Side of the Ring Season 7. Follow Stu Stone Instagram: https://www.instagram.com/stustone/ X: https://x.com/stustone ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Welcome Back, Hall of Famer 00:05:12 – Tom Green, Podcasting and the Early Internet 00:13:03 – Fame Then vs. Fame Now 00:19:07 – The Convention Circuit and Hollywood's New Residuals 00:29:02 – Convention Horror Stories 00:34:18 – Why Hollywood Doesn't Work Like It Used To 00:44:34 – The Death of the Movie Star 00:50:05 – Jamie's Early Hustle 00:56:57 – The SNL Audition 01:00:51 – Chasing a Record Deal 01:02:15 – How Rolling with Saget Was Born 01:09:01 – Going Number One on MySpace 01:10:37 – Convincing Warner Bros. to Make It 01:15:04 – Blowin' Up Turns 20 01:25:18 – T-Pain, Bow Wow and MTV Memories 01:29:03 – Wrapping Up ⸻⸻⸻⸻⸻ 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