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

Tom Shadyac Producer Tom McComas Stunt Coordinator Jeremy Fry Stunts Bill Collage Screenplay Andy Dylan Stunts Pete Turner Stunts Matthew F. Leonetti Director of Photography Joseph Middleton Casting Adam Cooper Screenplay Steve Pink Director Vanessa Motta Stunts Andy Koyama Sound Re-Recording Mixer Gregory J. Barnett Stunts Pat Romano Stunts Danny Downey Stunts Austin Priester Stunts Ronn Surels Stunts