Justin Long - Bartleby Gaines
Jonah Hill - Sherman Schrader
Adam Herschman - Glen
Blake Lively - Monica
Columbus Short - Hands
Maria Thayer - Rory
Lewis Black - Uncle Ben
Mark Derwin - Jack Gaines
Ann Cusack - Diane Gaines
Hannah Marks - Lizzie Gaines
Robin Taylor - Abernathy (A.D.D.) (as Robin Lord Taylor)
Diora Baird - Kiki
Brendan Miller - Wayne
Joe Hursley - Maurice
Jeremy Howard - Freaky Student
Anthony Heald - Dean Van Horne
Travis Van Winkle - Hoyt Ambrose
Kaitlin Doubleday - Gwynn
Sam Horrigan - Mike Welsh
Ross Patterson - Mike McNaughton
Artie Baxter - Mike Chambers
Kellan Lutz - Dwayne
Chantelle Tibbs - Confused Kid
Yorke Fryer - S. H. Student in Hallway
Skyler Stone - S. H. Student in Hallway
Jim Leung - S. H. Student in Hallway
Ernest Shaun Reyes - Random S. H. Student (as Shaun Reyes)
Lisa Gleave - Kiki’s Best Friend
Alejandra Gutierrez - Kiki’s Best Friend
Jim O'Heir - Mr. Schrader
Darcy Shean - Mrs. Schrader
Jay Harik - Family Friend
Mathew Vigil - Shoe Store Boy
Debbon Ayer - Shoe Store Mother
Carla Jimenez - Shoe Store Manager
Ned Schmidtke - Board Chairman
Tim Bagley - Vice Principal Matthews
Ray Santiago - Boy Going to Princeton
Margaret Travolta - Academic Counselor
Brian Powell - Economics Teacher
Jeff Duby - Stressed-out Student
Scott Adsit - Drop-off Dad
Lindy Loundagin - Drop-off Mom
Steve Little - Desk Clerk
Ethan Hova - Male Graduate
Criscilla Crossland - Go Go Dancer
Meredith Giangrande - Glen’s Party Girl
Christina Diaz - S. H. Testimonial Student
Zoe Di Stefano - S. H. Testimonial Student
David Carmon - S. H. Testimonial Student
Armen Weitzman - S. H. Testimonial Student
Christopher Khai - S. H. Testimonial Student
Nicholas Garren - S. H. Testimonial Student
Nina Nam - Fake I.D. Kid
Wendy Waller - Fake ID Kid
Ronnie Lewis Jr. - Fake I.D. Kid
Matthew Ching - Fake ID Kid
Richard Brown - Fake ID Kid
Mylika Davis - Fake ID Kid
Laurie Megan Phelps - Fake ID Kid (as Laurie Phelps)
Portis Hershey - Fake I.D. Kid
Shameka Banks - S. H. Testimonial Student
Natalia Bellami - Sorority Girl
Richard W. Blake - Frat Boy
Ashleigh Boiros - S H Testimonial
Kristin Bryant - Hot Sorority girl
Mike Daily - Stressed-out Student
Mindee de Lacey - Board Member
Don Dennis - Fake ID kid #11
Holly Fielding - Autograph Student
Kate French - Glen's Party Girl
Geoffrey Gould - Parents Day parent
Larke Hasstedt - Go Go Dancer
Louie Heredia - S. H. Testimonial Student
Jessica Jeensalute - Student Testimonial Girl
Michelle Laine - Hot Sexy Girl
Vanessa Lauren - S. H. Testimonial Student
Jamie Leffler - Fake ID Kid
Arthur Leo - ESL Student
Christian Long - Sandwich Mascot
Paraic McGann - BKE Pledge with Jacket
Matt Noble - Big Larry
Misty Odell - Student Testimonial Girl
Rebecca Parisi - Yoga Student
Neil Patil - Exchange student
Nathan Pitkanen - Slacker Student
Rumaisa Rahman - College Student
Jimmy Schueler - Frat Guy
Greg Sestero - Fraternity Guy
Matthew St. Clair - Fake ID Kid
Stephanie St. Hilaire - S. H. Testimonial Student
Chad Fernandez - Skater (uncredited)
Jason Kapraun - Drug Dealer (uncredited)
Meilinda Soerjoko - ESL student (uncredited)
