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

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

From HATE TO BREAK IT TO YA with Jamie Kennedy by Hate To Break It To Ya with Jamie Kennedy

May 20, 2026 · 1h 29m

About this episode

Jamie Kennedy interviews Harland Williams about his new film and their long friendship.

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…

People in this episode

Host: Jamie Kennedy

Guest: Harland Williams

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Mentioned in this episode

Books & works: Wingman

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