Rise to Fame
SNL fired him in 1995 after five years as a writer and cast member. Billy Madison had already come out in February and grossed $26M on a $10M budget, so the timing was awkward for the people who let him go. Happy Gilmore followed in 1996. He founded Happy Madison Productions in 1999, named after those two films. The guy NBC cut went on to sign a $250M deal with Netflix nearly two decades later.
In the Spotlight
Netflix paid him $250M for four films in 2014, then another $275M in 2020. The math works because his movies move, even when critics don't. Uncut Gems in 2019 changed the conversation. The Safdie Brothers got a performance out of him that earned 91% on Rotten Tomatoes, which gave critics permission to take him seriously for a minute. Happy Gilmore 2 landed on Netflix in July 2025 to mixed reviews and 46.7 million views in three days. His audience doesn't need the critics' permission.
Side Notes
He plays pickup basketball multiple times a week, real games, shows up alone in his signature oversized polo shirts and baggy shorts, no entourage, plays with whoever's on the court. Shaquille O'Neal called him 'definitely LA Fitness, 24-Hour Fitness legit.' In 2007 he donated $1 million to his hometown Boys & Girls Club in Manchester, New Hampshire, and when he announced it, his main memory of the place was basketball and ping pong.