All his life all Happy Gilmore (Adam Sandler) ever wanted to be was a hockey player. He couldn’t skate all that well, not could he steal or control the puck, but he had a slapshot that could kill, possibly literally. He had many jobs when he grew up, in many different kinds of fields, but all they pretty much did was pay the bills. The only thing Happy loves more than hockey is his grandmother (Frances Bay). Happy’s Grandma raised him after his parents split up, but now Happy is on his own, still chasing his dream of become one of the Boston Bruins, but due to his lack of discipline, things are about to change, in a big way.
Happy has been cut from the try-outs for who knows how many times now, and things are looking grim for Grandma, as she has not been able to pay her taxes in a very long time. The IRS is taking everything, and will be auctioning off the lovely house her husband built from the ground up decades ago. Happy’s girlfriend, Terry (Nancy McClure) has dumped him. Things just can’t seem to get much worse.