Man-child Billy Madison (Adam Sandler) has been a spoiled rich kid all his life and spends his days drinking and partying. When his father, hotel magnate Brian Madison (Darren McGavin), becomes fed up with his son's irresponsible ways, he issues an ultimatum. Since Billy passed all his schooling thanks to his father's influence and bribes, he must retake and pass every grade in 24 weeks. Otherwise, the business will be turned over to Brian's conniving associate, Eric Gordon (Bradley Whitford).