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.

Brewster, an aging minor-league baseball player, stands to inherit 300 million dollars if he can successfully spend 30 million dollars in 30 days without anything to show for it, and without telling anyone what he's up to... A task that's a lot harder than it sounds!

Arthur, that irrepressible drunk, tries to sober up and get a job. Meanwhile, Ralph Marolla is conniving to trick the hapless boozer into marrying his daughter so he can gain entrée to Arthur's $750 million fortune.

A drunken playboy stands to lose a wealthy inheritance when he falls for a woman that his family doesn't like.

Jason Carmichael is a popular New York City playwright in desperate need of a new writing partner who can provide him with inspiration. Phoebe Craddock is a small-town teacher who aspires to be a writer.