Billy Madison

Adam Sandler

Brian Madison

Darren McGavin

Eric Gordon

Bradley Whitford

Veronica Vaughn

Bridgette Wilson

Principal Max Anderson

Josh Mostel

Frank

Norm Macdonald

Jack

Mark Beltzman

Carl Alphonse

Larry Hankin

Juanita

Theresa Merritt

Miss Lippy

Dina Platias

Pete

Hrant Alianak

Cook

Vincent Marino

Rollo the Janitor

Christopher Kelk

Nodding 1st Grader

Marc Donato

Ted 'Old Man' Clemens

Jack Mather

Penguin

Keith Cole

Penguin

Chris Mei

O'Doyle (Grade 1)

Conor Devitt

Scotty Logan (Grade 1)

Jared Durand

Tricia Labonte (Grade 1)

Jessica Nakamura

2nd Grade Teacher

Helen Hughes

Lawn Guy

Lawrence Nakamura

2nd Grader

Jacelyn Holmes

3rd Grader

Justin Williams

Attractive Lady

Claire Cellucci

O'Doyle the Bus Driver

Chris Farley

Clown

Shane Farberman

Driver

Al Maini

Shane Faberman

Ernie (Grade 3)

Jared Cook

O'Doyle (Grade 3)

Christian Matheson

Kyle

Kyle Bailey

Dan (Grade 3)

Austin Pool

Butler

Vernon Chapman

Maid

Mandy Watts

Jennifer (Grade 3)

Stacey Wheal

Shanna Bresse

Tour Guide

Gladys O'Connor

4th Grade Teacher

Marcia Bennett

Nurse

Diane Douglass

Architect

Tim Herlihy

Architect

Frank Nakashima

Diane Douglas

Lunch Lady

Joyce Gordon

Pothead

Jordan Lerner-Ellis

Pothead

Daniel Lerner-Ellis

Mr. Oblaski

Robert Smigel

Nancy Connors

Melissa Korzenko

O'Doyle (Grade 9)

Colin Smith

Paul

Jeff Moser

Rod

Amos Crawley

Crazy Person

Tex Konig

Crazy Person

Eduardo Gómez

Joyce

Tanya Grant

Joyce

Tanya Grout

Tenth Grader

Matthew Ferguson

Tenth Grader

Benjamin Barrett

O'Doyle (Grade 12)

Sean Lett

Susan (Grade 3)

Shanna Bresee

Drama Teacher

Michael Ayoub

Lawrence Nakumara

Rock Singer

Gino Veltri

Principal

Jim Downey

Mr. O'Doyle

Bob Rodgers

Mrs. O'Doyle

Margo Wladyka

Newswoman

Allison Robinson

Haitian Gardener

Marcel Jean Gilles

High School Girl

Suzanna Shebib

Danny McGrath (uncredited)

Steve Buscemi

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

Jet Skier

Kevin Le Roy

Jet Skier

Kelly Childerhose

Fire-eater

Ken Shires