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The Weinsteins' secret shame: a teen comedy so bad it became legendary.
TMDB
40
Rotten Tomatoes
56

Playing for Keeps (1986)

So-bad-it's-goodPeak '80s cheeseAmateur hour

Overview

Comedy

An ambitious trio of inner-city high school grads tries to hit the big time by turning a run-down country hotel into a rock & roll resort with around-the-clock music and live entertainment. Standing in their way are fearful townsfolk, unscrupulous businessmen and the tax collector, all threatening to bring the curtain down on the teens' aspirations. But this is one threesome who refuses to give up on their lifelong goal without a fight — and a song.

Flag of USUS
Content warning
American dream fantasyUnderdog hustleYouthful delusionSmall-town resistance

Standout Aspects

Acting

Marisa Tomei somehow escaped to Oscar glory

Direction

Weinstein brothers' only directing credit—wonder why

Production

Shot in actual crumbling hotel, explains everything

Best for:Friends: Irony-fueled group roasting session required·Background: Perfect for folding laundry in confused silence·Rewatch: Masochists tracking every bizarre choice
Harvey Weinstein

Director

Harvey Weinstein

ReleasedOct 3, 1986
Runtime1h 42m
StatusReleased

Vibe

Pacefast
Intensitylow
Tonelight
Feellight
Miramax
Playing for Keeps Inc.

Top Cast

Leon W. Grant

Leon W. Grant

Silk

Marisa Tomei

Marisa Tomei

Tracy

Jimmy Baio

Jimmy Baio

Steinberg

Harold Gould

Harold Gould

Rockerfeller

Raymond J. Barry

Raymond J. Barry

Mr. Hatcher - Chloe's Father

John Randolph Jones

John Randolph Jones

Sheriff Billy Sullivan

Jery Hewitt

Jery Hewitt

Backhoe Driver

Anthony Marciona

Anthony Marciona

Ronnie Long

Ask about Playing for Keeps

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Trivia

This was Harvey Weinstein's sole directing credit; he never directed again. The universe agreed.

Cultural

A pre-fame Marisa Tomei appears briefly—she'd win her Oscar six years later, possibly out of sheer relief.

YouTube

Playing for Keeps (1986) - Trailer

Playing for Keeps (1986) - Trailer

Gallery

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