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Billy Madison is a 27 year-old man whose father Brian is the head of a major hotel chain. Even though he is groomed to replace his father who is about to retire, Billy is extremely immature and unmotivated in life. When Brian considers making Eric Gordon (whom Billy despises) his new replacement, Billy decides to prove to his father that he is capable of taking over. He must repeat grade school all over again (2 weeks for each grade) in order to take over the hotel empire. The further Billy progresses, the more Eric tries to derail Billy.
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 fathers 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.
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
Jack Mather
Ted 'Old Man' Clemens
Christopher Kelk
Rollo the Janitor
Marc Donato
Nodding 1st Grader
Keith Cole
Penguin
Chris Mei
Penguin
Conor Devitt
O'Doyle (Grade 1)
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