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Stay Cool

Shoulda. Coulda. Woulda.

23 Apr 2009
  • United States of America
94 mins
4.9
57 votes
  • Comedy
  • Romance
articleOverview personCast
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.
  • Mark Polish

    as Henry McCarthy
  • Winona Ryder

    as Scarlet Smith
  • Sean Astin

    as Big Girl
  • Hilary Duff

    as Shasta O'Neil
  • Josh Holloway

    as Wino
  • Jessica St. Clair

    as Darcy Portola
  • Frances Conroy

    as Mrs. Leuchtenberger
  • Marc Blucas

    as Brad Nelson
  • Joanna Cassidy

    as Mrs. Smith
  • Dee Wallace

    as Mrs. McCarthy
  • Michael Gross

    as Mr. McCarthy
  • Jon Cryer

    as Javier

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