Winona Ryder

Character: Scarlet Smith

Mark Polish

Character: Henry McCarthy

Sean Astin

Character: Big Girl

Hilary Duff

Character: Shasta O'Neil

Josh Holloway

Character: Wino

Jon Cryer

Character: Javier

Chevy Chase

Character: Principal Marshall

Jessica St. Clair

Character: Darcy Portola

Frances Conroy

Character: Mrs. Leuchtenberger

Marc Blucas

Character: Brad Nelson

Joanna Cassidy

Character: Mrs. Smith

Dee Wallace

Character: Mrs. McCarthy

Michael Gross

Character: Mr. McCarthy

Ken Johnson

Character: Mr. O'Neil

Jessica Schatz

Character: Mrs. O'Neil

Scott Michael Campbell

Character: Officer Bird

Blake Adams

Character: Cop

Catherine Black

Character: Goth Girl

Jenn Shagrin

Character: Jungle Journalist #1

Josh Sussman

Character: Jungle Journalist #2

Jane Sheldon

Character: Goth Girl Singer

Clark Hunter

Character: River Village Guard #1

John A. Keim

Character: River Village Guard #2

Jack Salvatore, Jr.

Character: Student in Hallway

Nick Thurston

Character: Party Kid

Kelly Wagner

Character: Nurse

Ashley Bell

Character: Valedictorian

David Shackelford

Character: John John

Ryan Best

Character: Disc Jockey

Emily Happe

Character: WRHS TV Host

Bon Ogle

Character: Bookstore Employee

Victoria Johnson

Character: Student Hollywood Reporter

Max Thieriot

Character: Shasta's Boyfriend

Brian Austin Green

Character: Narrator

Matthew Berke

Character: Tree Dwelling High School Student

Amanda Elliott

Character: Prom Date Girl

Irvin Scott Guillermo

Character: Senior

Shawn McDonald

Character: Franky (as Shawn Ronell McDonald)

Brent Rode

Character: Cannonball Guy

Nicole Smolen

Character: Student

Max Tsarev

Character: Wild Prom Boy / Basketball Player

Brad Benedict

Character: Senior Stud (uncredited)

Ashleigh Nicole Johnson

Character: Party Girl (uncredited)

Michael Justice

Character: Senior (uncredited)

Silver Tree

Character: Angie (uncredited)

Karmyn Tyler

Character: Beauty Shop Receptionist (uncredited)

Matthew Woodward

Character: Skater Kid (uncredited)