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The roast where Playboy met savage — Hef took hits from every angle.
TMDB
60

The N.Y. Friars Club Roast of Hugh Hefner (2001)

unhinged2000s comedycelebrity chaos

Overview

Comedy

The Comedy Central Roasts are a series of celebrity roast specials which air on the Comedy Central cable network. This one is for Hugh Hefner.

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Content warning

Standout Aspects

Acting

Gilbert Gottfried's nuclear Hefner jokes — career suicide as art form.

Writing

Punchlines that wouldn't survive a single tweet today.

Production

Friars Club atmosphere: cigars, red leather, barely controlled anarchy.

Best for:Streaming: Late-night YouTube rabbit hole when irony was still dangerous.·Friends: With friends who miss when roasts actually roasted.·Background: Half-listening while doomscrolling — you'll still hear the burns.
Heads up:Sexual Content: Relentless Hefner/Playboy sex jokes — it's basically the entire premise.·Language: Every slur and insult 2001 comedy allowed. Brace yourself.
Paul Miller

Director

Paul Miller

ReleasedMar 11, 2001
Runtime1h 19m
StatusReleased

Vibe

Pacefast
Intensityhigh
Tonemixed
Feellight

Top Cast

Hugh Hefner

Hugh Hefner

Self

Jimmy Kimmel

Jimmy Kimmel

Self

Alan King

Alan King

Self

Drew Carey

Drew Carey

Self

Adam Carolla

Adam Carolla

Self

Kylie Bax

Kylie Bax

Self

Cedric the Entertainer

Cedric the Entertainer

Self

Carson Daly

Carson Daly

Self

Tommy Davidson

Tommy Davidson

Self

Tom Fontana

Tom Fontana

Self

Gilbert Gottfried

Gilbert Gottfried

Self

Dick Gregory

Dick Gregory

Self

Patricia Hearst

Patricia Hearst

Self

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Deep Dive

Trivia, insights & behind the scenes

Cultural

This roast captures peak 'irony bro' comedy right before social media accountability nuked the genre. The Friars Club format itself died shortly after.

Trivia

Lisa Lampanelli's breakout performance here launched her as 'Queen of Mean' — she later called roasting 'the most honest art form.'

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