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