Billy Madison

Billy Madison is a spoiled rich kid who stands to inherit his father's hotel empire. However, his father has doubts about his ability to run the business and challenges him to complete all 12 grades of school in 24 weeks. Billy must navigate his way through elementary school, make new friends, and win over his teacher Veronica, all while trying to prove himself worthy of his father's legacy. But things get complicated when his father's executive vice president, Eric, tries to sabotage him and take over the company for himself. Will Billy be able to rise to the challenge and prove himself capable of running the family business?

You can stream Billy Madison on: Amazon Store

Some movies that have similar genres and were produced around the same time as Billy Madison include Me, Myself & Irene, Clerks, Liar Liar, Tommy Boy, Opportunity Knocks, Sour Grapes.