Mark Polish as Henry McCarthy

Winona Ryder as Scarlet Smith

Sean Astin as Big Girl

Hilary Duff as Shasta O'Neil

Josh Holloway as Wino

Jessica St. Clair as Darcy Portola

Frances Conroy as Mrs. Leuchtenberger

Marc Blucas as Brad Nelson

Joanna Cassidy as Mrs. Smith

Dee Wallace as Mrs. McCarthy

Michael Gross as Mr. McCarthy

Jon Cryer as Javier

Chevy Chase as Principal Marshall

Ken Johnson as Mr. O'Neil

Jessica Schatz as Mrs. O'Neil

Scott Michael Campbell as Officer Bird

Blake Adams as Cop

Catherine Black as Goth Girl

Jenn Shagrin as Jungle Journalist #1

Josh Sussman as Jungle Journalist #2

Jane Sheldon as Goth Girl Singer

Clark Hunter as River Village Guard #1

John A. Keim as River Village Guard #2

Jack Salvatore, Jr. as Student in Hallway

Nick Thurston as Party Kid

Kelly Wagner as Nurse

Ashley Bell as Valedictorian

David Shackelford as John John

Ryan Best as Disc Jockey

Bon Ogle as Bookstore Employee

Emily Happe as WRHS TV Host

Victoria Johnson as Student Hollywood Reporter

Max Thieriot as Shasta's Boyfriend

Brian Austin Green as Narrator