Stay Cool

Stay Cool (2009)

Shoulda. Coulda. Woulda.

Comedy Romance

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.

star 4.9
  • Release Date: 2009-04-23
  • Runtime: 1h 34min
  • Director: Michael Polish

Where to Watch Stay Cool Online

You can now watch Stay Cool online on the following streaming services in the United States.

    • Trailer

    Cast

    • Mark Polish

      Henry McCarthy

    • Winona Ryder

      Scarlet Smith

    • Sean Astin

      Big Girl

    • Hilary Duff

      Shasta O'Neil

    • Josh Holloway

      Wino

    • Jessica St. Clair

      Darcy Portola

    • Frances Conroy

      Mrs. Leuchtenberger

    • Marc Blucas

      Brad Nelson

    • Joanna Cassidy

      Mrs. Smith

    • Dee Wallace

      Mrs. McCarthy

    • Michael Gross

      Mr. McCarthy

    • Jon Cryer

      Javier

    • Chevy Chase

      Principal Marshall

    • Ken Johnson

      Mr. O'Neil

    • Jessica Schatz

      Mrs. O'Neil

    • Scott Michael Campbell

      Officer Bird

    • Blake Adams

      Cop

    • Catherine Black

      Goth Girl

    • Jenn Shagrin

      Jungle Journalist #1

    • Josh Sussman

      Jungle Journalist #2

    • Jane Sheldon

      Goth Girl Singer

    • Clark Hunter

      River Village Guard #1

    • John A. Keim

      River Village Guard #2

    • Jack Salvatore, Jr.

      Student in Hallway

    • Nick Thurston

      Party Kid

    • Kelly Wagner

      Nurse

    • Ashley Bell

      Valedictorian

    • David Shackelford

      John John

    • Ryan Best

      Disc Jockey

    • Bon Ogle

      Bookstore Employee

    • Emily Happe

      WRHS TV Host

    • Victoria Johnson

      Student Hollywood Reporter

    • Max Thieriot

      Shasta's Boyfriend

    • Brian Austin Green

      Narrator

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