The comedy film Billy Madison is about the son of a millionaire who has to go back to school in order to inherit his father's hotel company. Starring Adam Sandler, this is Sandler's first film as both head writer and leading actor. Sandler won a 1995 MTV Movie Award for the Best Comedic Performance for this role.

Brian Madison, played by McGavin, is retiring from the hotel business he owns and decides that his 27 year old son Billy is not suitable to take over the company. Billy commonly spends his days drinking by the pool and chasing an invisible penguin. When Billy hears of the change in leadership in Madison Hotels, he also learns that his father paid off his teachers when he was first in school, to get passing grades. Billy proposes a plan where if he completes first through twelfth grades again, he will take over the family business. His father accepts the plan and Billy enrolls in school, meeting all sorts of interesting people along the way.