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Cast Adam Herschman ..... Glen Alejandra Gutierrez ..... Kiki's Best Friend Ann Cusack ..... Diane Gaines Anthony Heald ..... Dean Richard Van Horne Artie Baxter ..... Mike Chambers Blake Lively ..... Monica Brendan Miller ..... Wayne Brian Powell ..... Economics Teacher Christopher Khai ..... S. H. Testimonial Student Columbus Short ..... Hands Holloway Darcy Shean ..... Mrs. Schrader David Carmon ..... S. H. Testimonial Student Diora Baird ..... Kiki Hannah Marks ..... Lizzie Gaines Jay Harik ..... Family Friend Jeff Duby ..... Stressed-out Student Jeremy Howard ..... Freaky Student Jim O'Heir ..... Mr. Schrader Joe Hursley ..... Maurice / The Ringers Jonah Hill ..... Sherman Schrader Justin Long ..... Bartleby Gaines Kaitlin Doubleday ..... Gwynn Kellan Lutz ..... Dwayne Lewis Black ..... Ben Lewis Lindy Loundagin ..... Drop-off Mom Lisa Gleave ..... Kiki's Best Friend Margaret Travolta ..... Academic Counselor Maria Thayer ..... Rory Thayer Mark Derwin ..... Jack Gaines Mathew Vigil ..... Shoe Store Boy Matt Noble ..... Big Larry Mike Daily ..... Stressed-out Student Ned Schmidtke ..... Board Chairman Nina Nam ..... Fake ID Kid Portis Hershey ..... Fake ID Kid Robin Taylor ..... Abernathy Darwin Dunlap Ross Patterson ..... Mike McNaughton Sam Horrigan ..... Mike Welsh Scott Adsit ..... Drop-off Dad Skyler Stone ..... S. H. Student in Hallway Steve Little ..... Desk Clerk Tim Bagley ..... Vice Principal Matthews Travis Van Winkle ..... Hoyt Ambrose Yorke Fryer ..... S. H. Student in Hallway

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