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
Jared Cook
Ernie (Grade 3)
Christian Matheson
O'Doyle (Grade 3)
Kyle Bailey
Kyle
Vernon Chapman
Butler
Mandy Watts
Maid
Austin Pool
Dan (Grade 3)
Gladys O'Connor
Tour Guide
Marcia Bennett
4th Grade Teacher
Diane Douglass
Nurse
Tim Herlihy
Architect
Frank Nakashima
Architect
Joyce Gordon
Lunch Lady
Jordan Lerner-Ellis
Pothead
Daniel Lerner-Ellis
Pothead
Robert Smigel
Mr. Oblaski
Melissa Korzenko
Nancy Connors
Colin Smith
O'Doyle (Grade 9)
Jeff Moser
Paul
Amos Crawley
Rod
Tex Konig
Crazy Person
Eduardo Gómez
Crazy Person
Tanya Grout
Joyce
Benjamin Barrett
Tenth Grader
Matthew Ferguson
Tenth Grader
Sean Lett
O'Doyle (Grade 12)
Stacey Wheal
Jennifer (Grade 3)
Shanna Bresee
Susan (Grade 3)
Michael Ayoub
Drama Teacher
Lawrence Nakamura
Lawn Guy
Gino Veltri
Rock Singer
James Downey
Principal
Bob Rodgers
Mr. O'Doyle
Margo Wladyka
Mrs. O'Doyle
Allison Robinson
Newswoman
Marcel Jean Gilles
Haitian Gardener
Suzanna Shebib
High School Girl
Justin Williams
3rd Grader
Nicholas A. Catalano
3rd Grader
Devon Codrington
3rd Grader
Nicole Harrison
3rd Grader
Lindsay Curran
3rd Grader
Brandi Tower
3rd Grader
Cassandra Forrester
3rd Grader
Matthew Tempest
3rd Grader
Michelle Toth
3rd Grader
Craig MacIsaac
3rd Grader
Tara Rooney
3rd Grader
Robby Cavallari
3rd Grader
Ryan Luis
3rd Grader
Alanna Budhoo
3rd Grader
Shomar Dejonge
3rd Grader
Carmela Bigioni
3rd Grader
Eric Aguilera
3rd Grader
Kevin Le Roy
Jet Skier
Kelly Childerhose
Jet Skier
Ken Shires
Fire-eater
Steve Buscemi
Danny McGrath (uncredited)
Chris Farley
Bus Driver (uncredited)