Justin Long
Bartleby Gaines

Jonah Hill
Sherman Schrader

Blake Lively
Monica Moreland

Adam Herschman
Glen

Columbus Short
Hands

Maria Thayer
Rory

Lewis Black
Uncle Ben

Jim O'Heir
Mr. Schrader

Mark Derwin
Jack Gaines

Ann Cusack
Diane Gaines

Hannah Marks
Lizzie Gaines

Robin Lord Taylor
Abernathy

Diora Baird
Kiki

Lisa Gleave
Kiki's Best Friend

Joe Hursley
Maurice / The Ringers

Jeremy Howard
Freaky Student

Anthony Heald
Dean Van Horne

Ross Patterson
Mike McNaughton

Sam Horrigan
Mike Welsh

Travis Van Winkle
Hoyt Ambrose

Kaitlin Doubleday
Gwynn

Kellan Lutz
Dwayne

Brendan Miller
Wayne

Skyler Stone
S. H. Student in Hallway

Darcy Shean
Mrs. Schrader

Brian Powell
Economics Teacher

Scott Adsit
Drop-off Dad

Steve Little
Desk Clerk

Parker Quinn
Frat Guy

Artie Baxter
Mike Chambers

Greg Sestero
Frat guy (uncredited)

Sara Jean Underwood
Girl By Pool (uncredited)

Alejandra Gutierrez
Kiki's Best Friend

Yorke Fryer
S. H. Student in Hallway

James Taku Leung
S. H. Student in Hallway

Jay Harik
Family Friend

Debbon Ayer
Shoe Store Mother

Carla Jimenez
Shoe Store Manager

Tim Bagley
Vice Principal Matthews

Ray Santiago
Boy Going to Princeton

Margaret Travolta
Academic Counselor

Ethan Hova
Male Graduate (scenes deleted)

Criscilla Anderson
Go Go Dancer

Meredith Giangrande
Glen's Party Girl

Kate French
Glen's Party Girl

Armen Weitzman
S. H. Testimonial Student

Christopher Khai
S. H. Testimonial Student

Mylika Davis
Fake ID Kid

Portis Hershey
Fake ID Kid