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.
Director Michael Polish
Trailer
Cast
Winona Ryder
Scarlet Smith
Brad Benedict
Senior Stud (uncredited)
Silver Tree
Angie (uncredited)
Karmyn Tyler
Beauty Shop Receptionist (uncredited)
Mark Polish
Henry McCarthy
Sean Astin
Big Girl
Hilary Duff
Shasta O'Neil
Josh Holloway
Wino
Blake Adams
Cop
Catherine Black
Goth Girl
Jon Cryer
Javier
Josh Sussman
Jungle Journalist #2
Nick Thurston
Party Kid
Jessica St. Clair
Darcy Portola
Ken Johnson
Mr. O'Neil
Jack Salvatore, Jr.
Student in Hallway
Max Thieriot
Shasta's Boyfriend
Chevy Chase
Principal Marshall
Marc Blucas
Brad Nelson
Frances Conroy
Mrs. Leuchtenberger
David Shackelford
John John
Emily Happe
WRHS TV Host
Dee Wallace
Mrs. McCarthy
Michael Gross
Mr. McCarthy
Scott Michael Campbell
Officer Bird
Ashley Bell
Valedictorian
Brian Austin Green
Narrator
Joanna Cassidy
Mrs. Smith