Billy Madison (Adam Sandler) is a 27 year old non-working immature idiot. His father Brian Madison (Darren McGavin) who runs Madison Hotels is retiring and is thinking of handing his company to Billy, but also thinking of giving it to Eric Gordon (Bradley Whitford), 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 liken (Dina Platias), (Helen Hughes I), and his sexy third grade teacher, Veronica Vaughn (Bridgette Wilson).