Adam Sandler stars as Billy Madison, a 27-year-old heir to a Fortune 500 hotel company who must repeat grades 1 through 12 to prove himself worthy of taking over the family business. Characterized by his immaturity and antics, Billy is aided in his efforts by Veronica Vaughn (Bridgette Wilson-Sampras) and eventually earns the respect of his classmates. As he navigates each grade, Billy faces opposition from his conniving vice president Eric Gordon (Bradley Whitford) before ultimately succeeding in proving himself worthy of leading the company.