Debbon Ayer
Shoe Store Mother
Margaret Travolta
Academic Counselor
Justin Long
Bartleby Gaines
Jeremy Howard
Freaky Student
Anthony Heald
Dean Van Horne
Jonah Hill
Sherman Schrader
Columbus Short
Hands
Kellan Lutz
Dwayne
Kaitlin Doubleday
Gwynn
Ray Santiago
Boy Going to Princeton
Tim Bagley
Vice Principal Matthews
Blake Lively
Monica Moreland
Adam Herschman
Glen
Maria Christina Thayer
Rory
Lewis Black
Uncle Ben
Mark Derwin
Jack Gaines
Ann Cusack
Diane Gaines
Hannah Marks
Lizzie Gaines
Robin Lord Taylor
Abernathy
Diora Baird
Kiki
Joe Hursley
Maurice / The Ringers
Alejandra Gutierrez
Kiki's Best Friend
Scott Adsit
Drop-off Dad
Travis Van Winkle
Hoyt Ambrose
Sam Horrigan
Mike Welsh
Ross Patterson
Mike McNaughton
Greg Sestero
Frat guy (uncredited)
Brendan Miller
Wayne
Meredith Giangrande
Glen's Party Girl
Steve Little
Desk Clerk
Parker Quinn
Frat Guy
Jay Harik
Family Friend
Brian Powell
Economics Teacher
Darcy Shean
Mrs. Schrader
Skyler Stone
S. H. Student in Hallway
Lisa Gleave
Kiki's Best Friend
Sara Jean Underwood
Girl By Pool (uncredited)
Artie Baxter
Mike Chambers
Armen Weitzman
S. H. Testimonial Student
Kate French
Glen's Party Girl
Carla Jimenez
Shoe Store Manager
Jim O'Heir
Mr. Schrader
Christopher Khai
S. H. Testimonial Student
James Taku Leung
S. H. Student in Hallway
Yorke Fryer
S. H. Student in Hallway
Portis Hershey
Fake ID Kid
Criscilla Anderson
Go Go Dancer
Ethan Hova
Male Graduate (scenes deleted)