Adam Sandler

Billy Madison

Darren McGavin

Brian Madison

Bridgette Wilson-Sampras

Veronica Vaughn

Bradley Whitford

Eric Gordon

Josh Mostel

Principal Max Anderson

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

Tim Herlihy

Architect

Joyce Gordon

Lunch Lady

Robert Smigel

Mr. Oblaski

Jack Mather

Ted 'Old Man' Clemens

Steve Buscemi

Danny McGrath (uncredited)

Keith Cole

Penguin

Chris Farley

Bus Driver (uncredited)

Chris Mei

Penguin

James Downey

Principal

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

Claire Cellucci

Attractive Lady

Claire Celluci

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

Frank Nakashima

Architect

Jordan Lerner-Ellis

Pothead

Daniel Lerner-Ellis

Pothead

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

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