Stay Cool

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.

Cast

Winona Ryder

Scarlet Smith

Mark Polish

Henry McCarthy

Sean Astin

Big Girl

Hilary Duff

Shasta O'Neil

Josh Holloway

Wino

Jon Cryer

Javier

Chevy Chase

Principal Marshall

Jessica St. Clair

Darcy Portola

Frances Conroy

Mrs. Leuchtenberger

Marc Blucas

Brad Nelson

Joanna Cassidy

Mrs. Smith

Dee Wallace

Mrs. McCarthy