Stay Cool (Stay Cool)

Shoulda. Coulda. Woulda.

Overview

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.

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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