 Billy Madison is a 27 year old non-working immature idiot. His father Brian Madison who runs Madison Hotels is retiring and is thinking of handing his company to Billy, but also thinking of giving it to Eric Gordon, a weasel-like co-worker of Madison Hotels. Billy strikes a deal with his father to go through grades 1-12 to earn the company. He still goofs off in school and tries to score with his teachers, including his sexy third grade teacher, Veronica Vaughn.