Bartleby Gaines
Justin Long
Sherman
Jonah Hill
Monica Moreland
Blake Lively
Rory
Maria Thayer
Hands
Columbus Short
Glen
Adam Herschman
Uncle Ben
Lewis Black
Dean Richard Van Horne
Anthony Heald
Derwin
Jack Gaines
Mr. Schrader
Jim O'Heir
Hoyt Ambrose
Travis Van Winkle
Jack Gaines
Mark Derwin
Diane Gaines
Ann Cusack
Kiki
Diora Baird
Lizzie Gaines
Hannah Marks
Abernathy
Robin Lord Taylor
Wayne
Brendan Miller
Maurice / The Ringers
Joe Hursley
Dwayne
Kellan Lutz
Kiki's Best Friend No. 1
Lisa Gleave
Freaky Student
Jeremy Howard
Mike McNaughton
Ross Patterson
Gwynn
Kaitlin Doubleday
Mike Welsh
Sam Horrigan
Mike Chambers
Artie Baxter
Confused Kid
Chantelle Tibbs
Sandwich Mascot
Christian Long
S. H. Student in Hallway No. 1
Yorke Fryer
S. H. Student in Hallway No. 2
Skyler Stone
Mrs. Schrader
Darcy Shean
Economics Teacher
Brian Powell
S. H. Student in Hallway No. 3
Jim Leung
Random S. H. Student
Shaun Reyes
Drop-off Dad
Scott Adsit
Drop-off Mom
Lindy Loundagin
Desk Clerk
Steve Little
Kiki's Best Friend No. 2
Alejandra Gutierrez
Frat Guy
Parker Quinn
Family Friend
Jay Harik
Frat guy (uncredited)
Greg Sestero
Shoe Store Boy
Mathew Vigil
Girl By Pool (uncredited)
Sara Jean Underwood
Shoe Store Mother
Debbon Ayer
Shoe Store Manager
Carla Jimenez
Board Chairman
Ned Schmidtke
Vice Principal Matthews
Tim Bagley
Boy Going to Princeton
Ray Santiago
Academic Counselor
Margaret Travolta
Stressed-out Student No. 1
Mike Daily
Stressed-out Student No. 2
Jeff Duby
Male Graduate
Ethan Hova
BKE Pledge with Jacket
Paraic McGann
ESL Student
Arthur Leo
Go Go Dancer No. 1
Criscilla Crossland
Go Go Dancer No. 2
Larke Hasstedt
Autograph Student
Holly Fielding
Glen's Party Girl No. 1
Meredith Giangrande
Glen's Party Girl No. 2
Kate French
Robin Taylor
S.H. Student in Hallway
Jimmy Leung
S.H. Testimonial Student
Zoe Di Stefano
S.H. Testimonial Student
Armen Weitzman
S.H. Testimonial Student
Christopher Khai
Fake ID Kid
Laurie Meghan Phelps
Pro Skater/BMX Rider
Jason Jones*