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.

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)

Michael Gross

(Mr. McCarthy)

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)

Emily Happe

(WRHS TV Host)

Bon Ogle

(Bookstore Employee)

Victoria Johnson

(Student Hollywood Reporter)

Max Thieriot

(Shasta's Boyfriend)

Brian Austin Green

(Narrator)

Matthew Berke

(Tree Dwelling High School Student)

Amanda Elliott

(Prom Date Girl)

Irvin Scott Guillermo

(Senior)

Shawn McDonald

(Franky (as Shawn Ronell McDonald))

Brent Rode

(Cannonball Guy)

Nicole Smolen

(Student)

Max Tsarev

(Wild Prom Boy / Basketball Player)

Brad Benedict

(Senior Stud (uncredited))

Ashleigh Nicole Johnson

(Party Girl (uncredited))

Michael Justice

(Senior (uncredited))

Silver Tree

(Angie (uncredited))

Karmyn Tyler

(Beauty Shop Receptionist (uncredited))

Jobeth Wagner

(Goth Girl (uncredited))

Matthew Woodward

(Skater Kid (uncredited))