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The most uncomfortable comedy about white kids who think they're in a rap video.
TMDB
54
IMDb
54
Rotten Tomatoes
13
Audience Score
45
Google
58
Watch(US)

Whiteboyz (1999)

cringe-core90s time capsulesuburban delusion

Overview

ComedyDramaMusic

In a virtually all-white Iowa town, Flip daydreams of being a hip-hop star, hanging with Snoop Doggy Dogg and Dr. Dre. He practices in front of a mirror and with his two pals, James and Trevor. He talks Black slang, he dresses Black. He's also a wannabe pusher, selling flour as cocaine. And while he talks about "keeping it real," he hardly notices real life around him: his father's been laid off, his mother uses Food Stamps, his girlfriend is pregnant, James may be psychotic, one of his friends (one of the town's few Black kids) is preparing for college, and, on a trip to Chicago to try to buy drugs, the cops shoot real bullets. What will it take for Flip to get real?

Flag of FRFRFlag of USUS
Content warning
cultural appropriationeconomic desperationracial identity confusionescapism vs reality

Standout Aspects

Acting

Danny Hoch's committed, deeply uncomfortable Flip.

Direction

Levin's documentary-style sting of real consequences.

Writing

Dialogue that weaponizes wannabe slang brilliantly.

Best for:Solo: So you can physically cringe in peace.·Friends: Watch someone's jaw drop at the flour-dealing scene.·Rewatch: Catch every ironic detail once you know the ending.
Heads up:Violence: Sudden police shooting scene is genuinely shocking.·Language: Constant racial slurs and offensive wannabe-Black dialogue.
Marc Levin

Director

Marc Levin

ReleasedSep 10, 1999
Runtime1h 32m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium
Fox Searchlight Pictures
Bac Films

Top Cast

Piper Perabo

Piper Perabo

Sara

Dr. Dre

Dr. Dre

Don Flip Crew #1

Fat Joe

Fat Joe

Don Flip Crew #2

Eugene Byrd

Eugene Byrd

Khalid

Dash Mihok

Dash Mihok

James

Mark Webber

Mark Webber

Trevor

Snoop Dogg

Snoop Dogg

Self

Lisa Jane Todd

Lisa Jane Todd

Trevor's Mom

Doug E. Fresh

Doug E. Fresh

Parking Lot Rapper #1

Danny Trejo

Danny Trejo

Prisoner

Ask about Whiteboyz

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Cultural

Released the same year as The Matrix and American Pie, this Sundance curiosity was immediately buried—too raw for comedy crowds, too satirical for drama audiences.

Insight

Dre and Snoop's cameos aren't endorsements; they're Greek chorus judgment, silently watching these kids cosplay their actual lives.

YouTube

Whiteboyz - trailer (1999)

Whiteboyz - trailer (1999)

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