Adam Sandler plays Billy Madison in the 1995 movie with the same name.

Billy is a non-working, non-educated 27 year-old slacker who spends his days drinking beer, reading girly magazines, and hanging out by the pool. He lives
entirely off his dad Brian Madison (Darren McGavin), a very rich man who has made his living in the hotel industry. madison sr. is retiring and is thinking of handing his company to Billy but realizes that Billy is unfit to run the family business, so he is also thinking of giving it to Eric Gordon (Bradley Whitford), a weasel-like co-worker of Madison Hotels. Billy strikes a deal with his father to go through grades 1-12 to earn the company.

Billy figures it will be no problem going back to high school and learning over again, until he learns that his father bought Billy's passing grades all the way back in elementary school. Thus, Billy must return to elementary school and pass each grade one at a time in a short time, or else he loses his place as heir to the company. In addition, Billy tries to win the hand of Veronica Vaughn (Bridgette Wilson), a sexy school teacher who thinks her students are more mature than Billy.