After the lord of darkness decides he will not cede his throne to any of his three sons, the two most powerful of them escape to Earth to create a kingdom for themselves. This action closes the portal filtering sinful souls to Hell and causes Satan to wither away. He must send his most weak but beloved son, Little Nicky, to Earth to return his brothers to Hell.
Failed hockey player-turned-golf whiz Happy Gilmore -- whose unconventional approach and antics on the grass courts the ire of rival Shooter McGavin -- is determined to win a PGA tournament so he can save his granny's house with the prize money. Meanwhile, an attractive tour publicist tries to soften Happy's image.
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.
Bobby Boucher is a water boy for a struggling college football team. The coach discovers Boucher's hidden rage makes him a tackling machine whose bone-crushing power might vault his team into the playoffs.
Mexican immigrant and single mother Flor Moreno finds housekeeping work with Deborah and John Clasky, a well-off couple with two children of their own. When Flor admits she can't handle the schedule because of her daughter, Cristina, Deborah decides they should move into the Clasky home. Cultures clash and tensions run high as Flor and the Claskys struggle to share space while raising their children on their own, and very different, terms.
A man who lost his family in the September 11 attack on New York City runs into his old college roommate. Rekindling the friendship is the one thing that appears able to help the man recover from his grief.