Billy Madison (1995)

This is a solid movie. Hotel magnate Brian Madison is about to retire and wants his son to manage the company, but there are concerns that he is not mature enough to handle the job. 27-year-old Billy Madison (Adam Sandler) is irresponsible and spends most of his time swimming in the pool, getting drunk, and playing pranks on the neighbors with his two best friends. To prove that he is smart enough to run the business, he is given a challenge by his father to repeat grades 1 through 12 in two week intervals. Meanwhile, Eric Gordon (Bradley Whitford) tries to sabotage Billy’s chances so he can become the next CEO instead.