Billy Madison (Sandler), a lazy and immature 27 year old man wants to inherit his father's (McGavin) company by going from 1-12 grades in less than 2 weeks. Billy must win the company from Eric Gordon (Whitford), a weasel-like co-worker. He still goofs off in all his classes and tries to "score" with all his teachers (Platias, Hughes) and his very sexy third grade teacher Veronica Vaughn (Wilson).