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lly Madison is the dimwitted, childish, and spoiled 27-year-old heir to Madison Hotels, a Fortune 500 chain of 650 hotels founded by his father, retiring tycoon Brian Madison. Billy spends his days drinking with friends and creating disturbances across his father's estate. One evening, Billy ruins a dinner meeting between his father and his associates by acting obnoxiously. Brian loses confidence in his son and chooses his devious executive vice president Eric Gordon to take over Madison Hotels. When Billy begs his father to reconsider his decision, as he knows how callous and cruel Eric is, Brian reveals that he secretly bribed Billy's school teachers to give him passing grades. The two finally compromise: Billy must complete all 12 grades of school, with two weeks for each grade, to prove he is competent enough to manage the company. Shortly after enrolling into elementary school, Billy becomes attracted to a third grade teacher na
med Veronica Vaughn, who initially ignores him. Nevertheless, Billy successfully progresses through his first two grades. He finds himself as one of Veronica's students in the third grade and earns her respect by standing up for Ernie, his friend and classmate. Billy becomes popular among the third graders and misses them as he advances through school. Billy's progress alarms Eric. Desperate to take over Madison Hotels, he blackmails Billy's elementary school principal, Max Anderson, into lying that Billy bribed him for passing grades, with a wrestling magazine containing pictures of Max's previous career as the "Revolting Blob", a masked wrestler who accidentally killed a man in the ring. Angered, Brian calls off his deal with Billy and renames Eric as chairman to the company. Billy grows distraught and reverts to his previous carefree lifestyle. Veronica motivates him to return to school, while his grade school classmates convince Max to retract his false
accusations, infuriating Eric. Brian agrees to give Billy another chance but Eric cites that Billy failed the challenge by not finishing ninth grade within two weeks. He then threatens to sue Brian if he does not pass the company onto him. Billy intervenes and challenges Eric to an academic decathlon to finally settle their feud with the winner getting to take over Madison Hotels. Both men excel in different activities, but Billy manages to take a single-point lead before the contest's final event, a Jeopardy!-style academic test. Billy gives a completely dimwitted answer for the opening question in the event, and Eric is given the chance to win the contest by answering a question regarding business ethics. Eric, being a highly unscrupulous businessman, cannot conceive of an answer and breaks down. He brandishes a revolver, but Max (in his wrestling gear) tackles Eric from backstage before he can harm Billy. Eric recovers from the attack and attempts to shoot Veronica, but he i
s shot in the buttock by Danny McGrath, a rifle-wielding madman whom Billy apologized to earlier for bullying him years ago. At his graduation ceremony, Billy, deciding that he is not fit for running a hotel company, announces he will pass Madison Hotels to Carl Alphonse, Brian's polite and loyal operations manager, and reveals he plans to attend college in order to become a teacher. Eric, walking on crutches due to his wound, watches on and fumes in frustration over Billy's decisio