The son of a successful businessman, Billy Madison (Adam Sandler) has spent his entire life doing nothing but having fun. Billy takes advantage of his father’s (Darren McGavin) wealth, spending his time partying with his friends and playing practical jokes at every opportunity. That is, until his father starts thinking about retiring and announces that he will leave his company to Eric (Bradley Whitford), a partner in his company. Billy strikes a deal with his dad to prove that he can be as responsible as anyone else and inherit the company: He will start over in school and complete every grade, 1-12. However, this proves to be more difficult than Billy thinks. Between Eric trying to thwart his plans, problems with other students, and a love interest in his third grade teacher, not to mention his love of beer, Billy may lose out on his inheritance.