Billy Madison

To inherit his family's fortune, Billy is going back to school... Way back.

Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2 weeks per grade, to prove that he has what it takes to run the family business.

Comedy

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))