Billy Madison is a 27 year-old man whose father Brian is the head of a major hotel chain. Even though he is groomed to replace his father who is about to retire, Billy is extremely immature and unmotivated in life. When Brian considers making Eric Gordon (whom Billy despises) his new replacement, Billy decides to prove to his father that he is capable of taking over. He must repeat grade school all over again (2 weeks for each grade) in order to take over the hotel empire. The further Billy...

Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he runs into a male gigolo who asks him to look after his precious fish while he is away on business. However, he wrecks the house and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer his hot on his trail.