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Stay Cool

Stay Cool

2011·Movie·1h 34m

Comedy, Romance

4.8 / 10 (59 votes)

Shoulda. Coulda. Woulda.

A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.

Directed by
Michael Polish
Original language
English
Released
16 September 2011

Where to Watch

Availability in the US · Subtitle and audio track data

Prime Video
Watch now →

Subtitle and audio languages not checked yet.

Last verified 2 Nov 2026

Cast

  • Winona Ryder

    Winona Ryder

    Scarlet Smith

  • Mark Polish

    Mark Polish

    Henry McCarthy

  • Sean Astin

    Sean Astin

    Big Girl

  • Hilary Duff

    Hilary Duff

    Shasta O'Neil

  • Josh Holloway

    Josh Holloway

    Wino

  • Jon Cryer

    Jon Cryer

    Javier

  • Chevy Chase

    Chevy Chase

    Principal Marshall

  • Jessica St. Clair

    Jessica St. Clair

    Darcy Portola

  • Frances Conroy

    Frances Conroy

    Mrs. Leuchtenberger

  • Marc Blucas

    Marc Blucas

    Brad Nelson

  • Joanna Cassidy

    Joanna Cassidy

    Mrs. Smith

  • Dee Wallace

    Dee Wallace

    Mrs. McCarthy