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*

Director

Steve Pink