A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.

When Longfellow Deeds, a small-town pizzeria owner and poet, inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big city, Deeds finds himself besieged by opportunists all gunning for their piece of the pie. Babe, a television tabloid reporter, poses as an innocent small-t...

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.

Arthur is a thirty-year-old child who will inherit 750 million dollars if he complies with his family's demands and marries the woman of their choosing.

Pinnacle records has the perfect plan to get their sinking company back on track: a comeback concert in LA featuring Aldous Snow, a fading rockstar who has dropped off the radar in recent years. Record company intern Aaron Green is faced with the monumental task of bringing his idol, out of control rock star Aldous Snow, back to LA for...