VH1 News Happy Gilmore After the surprise runaway success of Billy Madison (1995), Adam Sandler returned to theaters with Happy Gilmore on February 16, 1996. The (way) off-the-green golf comedy proved to be an immediate hit and quickly became an all-time gut-busting favorite, putting shoulder-to-shoulder alongside cinema’s other ruling hole-in-one-of hilarity, Caddyshack (1980). Over the course of the next two decades, Happy Gilmore has aged into a true classic. To celebrate 20 years of Happy Gilmore, then, here are 20 facts, figures, and inside stories regarding the movie that introduced us to Happy, Chubs, Shooter Gavin, and the brawling skills of Price Is Right host