Alex D. Linz as Max Keeble

Larry Miller as Principal Elliot T. Jindraike

Jamie Kennedy as Evil Ice Cream Man

Zena Grey as Megan

Josh Peck as Robe

Nora Dunn as Lily Keeble

Robert Carradine as Don Keeble

Noel Fisher as Troy McGinty

Orlando Brown as Dobbs

Amber Valletta as Ms. Dingman

Amy Hill as Mrs. Rangoon

Brooke Anne Smith as Jenna

Justin Berfield as Caption Writer

Romeo as Lil Romeo

Jonathan Osser as Worried Kid

Cory Hodges as Yearbook Photographer

Kyle Sullivan as Techie Kid

Shawn Pyfrom as Bus Prankster

Martin Spanjers as Runty Band Member

Bryan Matsuura as First Eighth Grader

Andy Morrow as Second Eighth Grader

Adam Lamberg as Eighth Grader On Bike

Nick Albert as Eighth Grader in Gym

Zachary Spound as Julius Klinghoffer

Maximilian Kesmodel as Four Year Old Max

Christian Boewe as Six Year Old Troy

Marcus Toji as Food Fight Chess Player

E.J. De la Pena as Pudgy 7th Grader

Ashly Holloway as Adorable 6 Yr. Old Girl

Brendan Hill as Pimply 7th Grader

Alexandra Kaplan as Kelly Lloyd

Nicholas King as Skater Wannabe

Clifton Davis as Supt. Bobby 'Crazy Legs' Knebworth

Veronica Alicino as Mrs. Talia

Greg Lewis as Janitor

Chely Wright as Mrs. Styles

Dennis Haskins as Mr. Kohls

Teddy Lane Jr. as Phys Ed Teacher

Countess Vaughn as Office Admin. Assistant

Tony Hawk as Tony Hawk

Hopsin as Pizza Parlor Kid

Jordan Mahome as Marley

Myra as Chelsea

Sarah Rush as Ms. Lane

Chelsea Bond as Mrs. Didion

Maximillian Kesmodel as 4 Year Old Max

P.J. Byrne as DJ/ Young Executive (Uncredited)