Billy Madison is the 27-year-old heir to a Fortune 500 hotel company that his father, Brian, has created. He spends his days drinking with friends and creating disturbances across his father's estate. One day, Billy ruins a dinner meeting between his father and his associates by acting obnoxiously. Brian loses confidence in his son and chooses the conniving Eric Gordon as his successor. When Billy begs his father to reconsider his decision, 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 in two week intervals to prove he is competent enough to manage the company.