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

Marc Donato

Nodding 1st Grader

Jacelyn Holmes

2nd Grader

Marcia Bennett

4th Grade Teacher

Tim Herlihy

Architect

Joyce Gordon

Lunch Lady

Robert Smigel

Mr. Oblaski

Amos Crawley

Rod

Tanya Grant

Joyce

Matthew Ferguson

Tenth Grader

Michael Ayoub

Drama Teacher

Jim Downey

Principal

Steve Buscemi

Danny McGrath (uncredited)

Chris Farley

Bus Driver (uncredited)