Haileywood

Latest Episodes:

Taye Diggs on Trauma, Ambition, and the Discomfort of Sitting Still Sep 25, 2026

Show notes

Ryan sits down with actor Taye Diggs for a deeply personal conversation about the drive to keep achieving — and what happens when you finally stop. Taye opens up about growing up around poverty and abuse, being bullied for his dark skin, and discovering a sense of belonging and possibility through theater. He looks back at joining the original cast of Rent, becoming an unexpected sex symbol in How Stella Got Her Groove Back, and the ambition that kept him chasing the next level even as his dreams were coming true. They explore how divorce and fatherhood upended the life he thought he had figured out, why even spirituality can become another form of striving, and the possibility that after a lifetime of searching, the next step isn’t another practice or achievement at all. Maybe it’s simply learning to stop, sit with what’s there, and hear the words: “Relax. You’re okay.”

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Very Special Episodes: Live From New York, It's Your Grandmother Feb 14, 2025

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During its first 50 seasons, Saturday Night Live has welcomed legendary actors, superstar athletes, and notable politicians. But for one memorable night in 1977, Lorne Michaels turned the show over to an 80-year-old amateur.

Hosted by Dana Schwartz, Zaron Burnett, and Jason English
Written by Jake Rossen
Produced by Josh Fisher
Editing and Sound Design by Chris Childs
Mixing and Mastering by Chris Childs
Original Music by Elise McCoy
Show Logo by Lucy Quintanilla
Executive Producer is Jason English

Special thanks to Connie Crawford for sharing her story. And thanks to the great Bill Carter for stopping by! You can read more of his work at LateNighter, or check out his many classic books.

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Episode 8: Until Further Notice Dec 22, 2021

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Things come to a head in Hailey as Bruce Willis enlists the help of a rogue security force to chase unwanted visitors out of town. Soon, a life-altering event threatens to end the love affair between Willis and Hailey.

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Episode 7: Homecoming Dec 15, 2021

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Hailey, Idaho isn’t the only small town Bruce Willis wants to remake. He sets his sights on Penn's Grove, New Jersey, his actual hometown, and promises big things to come for the economically-strapped region. But red tape and negative press threaten to leave the town with a broken heart—and leave Hailey wondering if they’re still on Willis’ good side.

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Episode 6: A Bruce Willis Production Dec 08, 2021

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Willis announces he’s starring in and producing a major feature film - a Kurt Vonnegut adaptation - that will be shot in the state of Idaho. He even gives some local actors their big screen breaks. But in a bid to retain almost complete creative control, Willis upends both his career and the lives of his Idahoan neighbors.

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Episode 5: Citizen Willis Dec 01, 2021

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Small town bureaucracy slows Willis’ ambitions, the police go after his inner circle and some Hailey residents are just saying no to Bruce. When lawsuits start popping up, Willis steps out of the shadows and flexes his political muscle. It turns into a statewide battle when the federal government proposes dumping nuclear waste 60 miles away from Hailey.

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Episode 4: Mint Condition Nov 17, 2021

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Bruce Willis opens his biggest investment in Hailey yet—the two-story Mint bar and nightclub. Major acts draw modest crowds, but the real attraction is Willis and his band, who show up unannounced and rock long into the night. But having a major nightlife hotspot in the sleepy town leads to some big city problems, problems that leave some wondering where did the real Hailey go?

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Episode 3: Planet Haileywood Nov 10, 2021

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Willis ventured into big business with his gimmicky Planet Hollywood franchise, but after being a quiet Hailey resident for several years, Willis buys and renovates a restaurant and bar, and soon an old movie theater. When blockbuster Hollywood premieres start happening on Hailey's main street, residents soon realize that Willis' persona casts a big shadow.

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Episode 2: Welcome to the Party, Pal Nov 03, 2021

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An incident involving an angry Willis and even angrier police officers prompts the star to rethink his life in the spotlight. Just when Willis has had enough, an accident opens the door to a different life in Hailey, Idaho.

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Episode 1: His Own Private Idaho Oct 27, 2021

Show notes

As one of the most famous movie stars in the world, there aren’t many places Bruce Willis can feel comfortable. He decides to exit Los Angeles and seek solace in a tiny Idaho town in the hopes he can blend in as a regular guy. But can anyone thirty feet tall on movie screens ever seem small?

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