Harland Williams Wrote, Directed & Starred in a Movie — And Ryan Gosling House Sat for Him | Ep 257

This week on Hate To Break It To Ya I sat down with Harland Williams — Canadian-born comedian, cult movie icon, and one of the most genuinely original minds I've encountered in 30 years of this business — and I have to tell you, this one got weird fast and I loved every second of it. We've known each other for three decades, and somehow this is the first time we've really gone deep on camera. Buckle up. We covered a lot of ground. Harland just wrote, directed, and starred in his new comedy film Wingman — out now on streaming — and the backstory of how it got made is almost as funny as the movie itself. He sent the script to Will Ferrell, Jim Carrey, Jason Bateman, and Ryan Gosling — yes, that Ryan Gosling, who used to house-sit for Harland and sleep in his guest room before he broke. None of them said yes, so Harland looked in the mirror and cast himself. He also fought hard to bring Kayla Wallace in from British Columbia at extra cost, insisted on Russell Peters doing an East Indian accent on screen for the first time ever, and cast me as the villain — a rival wingman named Eddie with a long wig and a Clint Eastwood stare-down energy. We even watched a scene from the film right here on the pod. The movie has set pieces, heart, and a dark secret between our two characters that you won't see coming. But that's only half the conversation. Harland also went on record — publicly, for the first time — saying Richard Pryor and George Carlin never made him laugh. He'd take the Purple Rice guy from the Laugh Factory over either of them any day. We got into why so many comedians give the exact same answer when asked about their influences, whether that's conditioning or something weirder, and why Harland refuses to punch down at any comedian no matter how they got here. We also talked California — the taxes, the homeless crisis, the empty fire reservoirs, the delta smelt — and why this state is still a jewel that somebody needs to polish. Harland Williams is one of a kind. This conversation reminded me exactly why. ⸻⸻⸻⸻⸻ About Harland Williams: Harland Williams is a Canadian-American comedian and actor best known for his scene-stealing roles in Dumb and Dumber, There's Something About Mary, Half Baked, RocketMan, and Sorority Boys. He is the creator of the Disney Junior animated series Puppy Dog Pals, an author and illustrator of children's books, and the host of The Harland Highway podcast. His new film Wingman — which he wrote, directed, and stars in alongside Russell Peters, Jamie Kennedy, and Kayla Wallace — is now streaming. He is currently on his 2026 Comzilla Comedy Tour across the United States. Follow Harland Williams Instagram: https://www.instagram.com/harlandwilliams/ X: https://x.com/HARLANDHIGHWAY Website: https://www.harlandwilliams.com ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Hot Cocoa Suspicion & Mic Arm Intro 00:05:09 – Harland's New House & Loving California 00:09:51 – California's Problems: Taxes, Homelessness & Mismanagement 00:17:01 – The LA Fires, Empty Reservoirs & the Delta Smelt 00:22:10 – Stupidity vs. Conspiracy: Wrong Directors in the Wrong Seats 00:27:28 – The Comedy Pipeline Then vs. Now 00:30:13 – Purple Rice: The Unknown Comic Who Lived Rent-Free for 40 Years 00:36:28 – Art Directs Us — Not the Other Way Around 00:39:56 – Harland Quits His Busboy Job & Goes to See Purple Rain 00:43:00 – George Carlin, Richard Pryor & Comedy Conditioning 00:53:03 – Is Comedy Just About the Laugh? 01:00:25 – Wingman: The Movie — Origin Story & 16 Years in the Making 01:02:00 – Ryan Gosling House-Sat for Harland (And His Sisters Know It) 01:05:44 – Casting Wingman: Kayla Wallace, Russell Peters & Michael Rosenbaum 01:13:47 – The Koala, the Set Pieces & What Makes Wingman Different 01:21:28 – The Toothpick Showdown & Jamie's Character Eddie 01:24:10 – Wingman Is Out Now — Where to Watch & Tour Info ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy ⸻⸻⸻⸻⸻ Harland Williams, Harland Williams interview 2026, Wingman movie 2026, Jamie Kennedy podcast, Hate To Break It To Ya, Harland Williams Wingman, Russell Peters Wingman, Ryan Gosling house sitter, Dumb and Dumber cast, Half Baked cast, Harland Highway podcast, comedy cannibalism stand-up Learn more about your ad choices. Visit podcastchoices.com/adchoices