John Quincy Archibald is a father and husband whose son is diagnosed with an enlarged heart and then finds out he cannot receive a transplant because HMO insurance will not cover it. Therefore, he decides to take a hospital full of patients hostage until the hospital puts his son's name on the donor's list.
Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2 weeks per grade, to prove that he has what it takes to run the family business.
When Berke Landers, a popular high school basketball star, gets dumped by his life-long girlfriend, Allison, he soon begins to lose it. But with the help of his best friend Felix's sister Kelly, he follows his ex into the school's spring musical. Thus ensues a love triangle loosely based upon Shakespeare's "A Midsummer Night's Dream", where Berke is only to find himself getting over Allison and beginning to fall for Kelly.
