Keith

Elisabeth Harnois

Natalie

Jesse McCartney

Keith

Ignacio Serricchio

Raff

Margo Harshman

Brooke

Michael McGrady

Pete

Jennifer Grey

Caroline

Michael O'Keefe

Alan Ascher

Ethan Phillips

Mr. Miles

Eric Parker

Travis

Jessy Schram

Courtney

Micah Henson

Shane

Ian Nelson

Brian

Tabitha Brownstone

Cynthia

Sam Murphy

Zach

Sarah Zinsser

Office Lady

Ron Carlson

English Teacher

Megan Hubbell

Officious Girl

Courtney Halverson

Junior Girl

Janice Kent

Woman

Zack Rockefeller

Billy

Jan Devereaux

Secretary

Rachel Thorp

Girl

Tim Halligan

Father

Michael Bryan French

Principal Sassen

Gareth Williams

Henry

Lee Turner

Joe

Jesse Heiman

Chemistry Class Student (uncredited)

Victoria Chalaya

Lea (uncredited)

Dennis Cockrum

Assistant Principal (uncredited)

Rance Howard

Old Man (uncredited)