Justin Long

Bartleby Gaines

Jonah Hill

Sherman Schrader

Blake Lively

Monica Moreland

Adam Herschman

Glen

Columbus Short

Hands

Maria Thayer

Rory

Lewis Black

Uncle Ben

Jim O'Heir

Mr. Schrader

Mark Derwin

Jack Gaines

Ann Cusack

Diane Gaines

Hannah Marks

Lizzie Gaines

Robin Lord Taylor

Abernathy

Diora Baird

Kiki

Lisa Gleave

Kiki's Best Friend

Joe Hursley

Maurice / The Ringers

Jeremy Howard

Freaky Student

Anthony Heald

Dean Van Horne

Ross Patterson

Mike McNaughton

Sam Horrigan

Mike Welsh

Travis Van Winkle

Hoyt Ambrose

Kaitlin Doubleday

Gwynn

Kellan Lutz

Dwayne

Brendan Miller

Wayne

Skyler Stone

S. H. Student in Hallway

Darcy Shean

Mrs. Schrader

Brian Powell

Economics Teacher

Scott Adsit

Drop-off Dad

Lindy Loundagin

Drop-off Mom

Steve Little

Desk Clerk

Parker Quinn

Frat Guy

Artie Baxter

Mike Chambers

Greg Sestero

Frat guy (uncredited)

Sara Jean Underwood

Girl By Pool (uncredited)

Alejandra Gutierrez

Kiki's Best Friend

Yorke Fryer

S. H. Student in Hallway

James Taku Leung

S. H. Student in Hallway

Jay Harik

Family Friend

Debbon Ayer

Shoe Store Mother

Carla Jimenez

Shoe Store Manager

Ned Schmidtke

Dr. J. Alexander

Tim Bagley

Vice Principal Matthews

Ray Santiago

Boy Going to Princeton

Margaret Travolta

Academic Counselor

Ethan Hova

Male Graduate (scenes deleted)

Criscilla Anderson

Go Go Dancer

Meredith Giangrande

Glen's Party Girl

Kate French

Glen's Party Girl

Armen Weitzman

S. H. Testimonial Student

Christopher Khai

S. H. Testimonial Student

Mylika Davis

Fake ID Kid

Portis Hershey

Fake ID Kid