Adam Sandler
Billy Madison
Bradley Whitford
Eric Gordon
Josh Mostel
Principal Max Anderson
Bridgette Wilson-Sampras
Veronica Vaughn
Darren McGavin
Brian Madison
Norm Macdonald
Frank
Mark Beltzman
Jack
Larry Hankin
Carl Alphonse
Theresa Merritt
Juanita
Dina Platias
Miss Lippy
Hrant Alianak
Pete
Vincent Marino
Cook
Christopher Kelk
Rollo the Janitor
Marc Donato
Nodding 1st Grader
Keith Cole
Penguin
Chris Mei
Penguin
Conor Devitt
O'Doyle (Grade 1)
Jared Durand
Scotty Logan (Grade 1)
Jessica Nakamura
Tricia Labonte (Grade 1)
Helen Hughes
2nd Grade Teacher
Jacelyn Holmes
2nd Grader
Jack Mather
Ted 'Old Man' Clemens
Claire Cellucci
Attractive Lady
Shane Farberman
Clown
Al Maini
Driver