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Punch-Drunk Love (2002):
Whenever I see an ad for the latest poor comedy Sandler is about to release, be it Bedtime Stories or You Don’t Mess with the Zohan, I always remind myself of this film. With Punch-Drunk Love, Sandler proved he can step out of his comfort zone and do some legitimately great acting — while still being funny. Sandler stars as Barry Egan, a business owner who is desperately lonely and suffers from anger management issues due to his overbearing and abusive sisters. When Barry meets Lena (Emily Watson), he immediately falls for her, but has trouble showing this affection. Meanwhile, Barry must also deal with a phone sex hotline that is attempting to steal all of his money, and successfully completing his goal of buying pudding that gives him frequent flyer miles for less than the actual retail price. Sandler has tried dramatic roles since then (Spanglish and Funny People, a movie which I absolutely loathe), but never as successfully as in this film. Directed by Paul Thomas Anderson, this is far and away Sandler’s best performance, and surprisingly nuanced.
Happy Gilmore (1995):
I hate when people compare this film to Caddyshack. One is a classic with three comedy gods on display, while the other has Sandler and a surprisingly funny Carl Weathers. It’s no contest. That said, Happy Gilmore is a funny movie in its own right, and one could make the argument that it is Sandler’s best comedy. Sandler stars as Gilmore, a hockey player who isn’t too good at the sport he loves. When he finds out his grandmother owes thousands of dollars in back taxes, he takes up golfing due to his uncanny ability to drive the ball 400 yards. Filled with physical gags and the trademark Sandler silliness, Gilmore is a trademark ‘90s comedy.
Billy Madison (1994):
Remember when Adam Sandler was energetic and would do seemingly anything for a laugh? That’s on display in this movie more than any other. As a man-child who goes back to school to prove to his father that he is mature enough to run a company, Sandler spends most of the movie talking in silly voices or yelling at small, innocent children. To be honest though, my favorite actors in the movie are Chris Farley and Norm MacDonald, who both make the most out of their limited screen time by supplying as many jokes as they can possibly fit into their roles.
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