Billy Madison (Adam Sandler), a 27-year-old heir to a wealthy father, has spent his entire life reaping the benefits of his family's hotel chain with 650 properties, Madison Hotels, a Fortune 500 company. 61,000 people work for the hotel chain. He spends his days drinking with best friends, Jack (Mark Beltzman) and Frank (Norm Macdonald), and creating disturbances across his father's estate. Billy is so baked in the sun and on drugs that he sees Penguins chasing him everywhere. Billy feels that it is too hot for penguins and wants to capture them and send them back to colder climates. Juanita (Theresa Merritt) is the house maid and cares for Billy. One day, Billy ruins a dinner meeting between his father, Brian (Darren McGavin), and his business associates. Billy is very late arriving for the dinner and then acts obnoxiously after being instigated by Eric Gordon (Bradley Whitford), Brian's executive vice president. This prompts Brian to lose any remaining faith in Billy, as he chooses the conniving Eric to become the next CEO of the company. Brian also passes over Carl, who is a senior and loyal employee to the company for his entire working life of 25 years. Brian said that he and his now deceased wife always wanted to turn over their empire to Billy, but Eric argues that the 61,000 employees will have their jobs in danger when Billy takes over. When Billy, who despises Eric, protests that he can be responsible, Brian reveals that he secretly bribed all of Billy's school teachers in order for him to pass. Billy begs his father to reconsider his decision. The two finally come to a compromise: Billy must pass elementary, middle, and high school (grades 1-12) on his own within the course of twenty-four weeks (two weeks per grade), in order to prove his competence. Miss Lippy (Dina Platias) is Billy's first grade teacher, where he reads stories and plays dodge ball. Billy is brutal with the other kids at dodge-ball. Billy has a lot of trouble with simple hand eye coordination required to create a cotton snow-man. The urinals for first grade are too small for Billy. He passes first grade when he draws a blue duck. Every time Billy passes a grade, he throws a grand party for all his fellow students at his mansion. Rollo is the school janitor who brings news of Billy's progress to Eric. Billy passes 2nd grade after completing the spelling bee correctly. Shortly after enrolling into school, Billy becomes attracted to a third-grade teacher named Veronica Vaughn (Bridgette Wilson), who initially is disgusted with Billy and finds his enrollment to be a distraction for the other students. He eventually finds himself as one of Veronica's students and earns her respect by defending Ernie (Jared Cook), his friend and classmate. Eric peed his pants while on a class trip and to save him from embarrassment, Billy throws water on his pants and pretends that peeing in pants is cool. The whole class pees inside their own pants. Billy starts getting Valentine cards from the pretty girls in school, but he has the hots for Veronica. Billy becomes popular among the third graders and begins to miss them as he advances through school. Veronica and Billy hook up after he passes 3rd grade. Carl warns Billy that Eric is up to something. When Billy reaches ninth grade, he finds that rather than being the cool guy that everyone looks up to, he is now considered a loser; realizing how it feels to be on the receiving end of bullying, he calls up an old classmate, Danny McGrath (Steve Buscemi), and apologizes for the way he treated him in high school. Danny accepts his apology and crosses his name off a list of people to kill. Billy's progress frustrates and alarms Eric, leading him to take the offensive while Billy struggles in high school. He visits Billy's grade school principal, Max Anderson (Josh Mostel), and threatens to reveal his past as a professional wrestler that is filled with controversial incidents, especially a particular one back in 1983, when Max accidentally caused the death of another man while performing a stunt. Coerced, Max publicly states he took bribes from Billy in return for passing him. The announcement angers Brian who chooses to give the hotel chain to Eric. Billy becomes distraught and reverts to his original care-free lifestyle. Veronica and others come to Billy's aid, convincing him to keep fighting Eric. He returns to school and begins to study again; however, Billy realizes that he must reclaim the hotel chain. His grade school friends visit Max at his home and convince him to retract his previous statements. Veronica encourages Billy to practice by removing one piece of clothing for every correct answer he gives. With Billy's named cleared, Brian and Carl Alphonse (Larry Hankin), a loyal, long-time employee of Madison Hotels argue to Eric that Billy deserves another chance, but Eric disagrees and threatens to file a lawsuit. Billy challenges Eric to an academic decathlon that will determine his father's successor. Although both men excel in different activities, Billy manages to take a single-point lead before the contest's final event, a Jeopardy! style academic test. The game progresses as Eric is given the chance to answer and potentially win. However, he is asked to answer a question about business ethics, of which he has no concept, and begins to break down. Refusing to admit defeat, he brandishes a gun at Billy. Max, clad in his wrestling outfit, subdues Eric. The attack fails to keep Eric down and laughing maniacally, he makes a final attempt to get revenge on Billy by turning his gun on Veronica. Suddenly, Danny McGrath appears with a high-powered rifle and disables Eric by firing a single shot into his buttocks. Danny and Billy share a quick wave, before he departs. At Billy's graduation, he announces that he is passing the hotel business to Carl and will instead attend college with hopes of becoming a teacher.
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