Darren McGavin

Brian Madison

Adam Sandler

Billy Madison

Norm Macdonald

Frank

Larry Hankin

Carl Alphonse

Josh Mostel

Principal Max Anderson

Bradley Whitford

Eric Gordon

Bridgette Wilson-Sampras

Veronica Vaughn

Marc Donato

Nodding 1st Grader

Tim Herlihy

Writer

Hrant Alianak

Pete

Jacelyn Holmes

2nd Grader

Tamra Davis

Director

Mark Beltzman

Jack

Theresa Merritt

Juanita

Dina Platias

Miss Lippy

Vincent Marino

Cook

Christopher Kelk

Rollo the Janitor

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

Jack Mather

Ted 'Old Man' Clemens

Claire Cellucci

Attractive Lady

Shane Farberman

Clown

Fitch Cady

Executive Producer