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Billy Madison
Billy Madison is a dimwitted, immature, and spoiled 27-year-old heir to Madison Hotels, a Fortune 500 company founded by his father, Brian Madison. Rather than preparing to take over the family business, Billy spends his days partying with friends and causing chaos on the estate. After he embarrasses his father during an important dinner meeting, Brian, who is retiring soon, decides to hand control of the company to his conniving vice president, Eric Gordon.
When Billy pleads for another chance, Brian reveals that he bribed teachers to help Billy pass school. The two strike a deal: Billy must complete grades 1 through 12, spending two weeks on each grade, to prove he is capable of running the company. Billy returns to elementary school, where he gradually earns the respect of his classmates and third grade teacher, Veronica Vaughn, especially after standing up for a fellow student.
Billy's rapid academic progress alarms Eric, who learns elementary school principal Max Anderson was once the professional wrestler called "the Revolting Blob", who accidentally killed an opponent in the ring. He uses this knowledge to blackmail Max into falsely claiming that Billy bribed him. As a result, Brian cancels the agreement and reinstates Eric as his successor. Discouraged, Billy drops out, but Veronica and his former classmates convince him to return. Max later confesses the truth, and Brian allows Billy to resume the challenge. When Eric objects, Billy proposes an academic decathlon to settle the matter.
After a series of competitive events, Billy takes a narrow lead. In the final round—a Jeopardy! -style quiz—Eric selects "reflections of society in literature" for Billy's final category. Billy fumbles his answer but selects " business ethics " for Eric's final category. Unable to respond, Eric suffers a breakdown, pulls a gun on Billy, and is stopped by Max, who dons his Revolting Blob costume. Eric then attempts to harm Veronica but is shot by Danny McGrath, a former classmate Billy once bullied and later apologized to.
At graduation, Billy announces that he will not take over Madison Hotels, but instead, he entrusts the company to loyal operations manager Carl Alphonse. Billy expresses his desire to go to college and pursue a teaching career, while a defeated and injured Eric watches in frustration.