Adam Sandler’s Best Movie Is Incredibly Hard To Watch

Billy Madison has a simple premise, and is basically the ’90s version of Rodney Dangerfields’ Back to School. The story centers on its titular character (Adam Sandler), a juvenile, day-drinking, obnoxious slacker on the wrong side of his 20s who has coasted through his entire life up to this point. Billy’s father, Brian (Darren McGavin), the founder and owner of Madison hotels, doesn’t believe that his son is capable of taking over the company when he retires, and is on the verge of letting his vice president, Eric Gordon (Bradley Whitford) take over the business.

Given how poorly Billy performed in school on his first go-around, Brian gives him one last chance to redeem himself by challenging him to go back to grade-school and prove that he’s intelligent enough to take over the family business.