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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.
Vicky, an out-of-work actress, struggling waitress and lesbian has her whole life thrown into turmoil when her father comes from Germany to visit. The main problem is that Vicky has told him she is a successful actress and happily married. She enlists the help of a gay friend to play her husband. Using a large range of characters—gay, lesbian, straight, transsexuals—the film creates a funny and touching view of family dynamics and sexuality.
