5. Punch Drunk Love-
Sandler's first attempt at serious acting on a wide scale. Sandler took his time and picked a good script with a great director (Paul Thomas Anderson) to launch his attempt to break the mold of comedies that he was in. It worked out in ways that few would have predicted as Sandler went on to gain a number of awards for his performance. This film is also a wonderful take on the characters that Sandler often plays,,, especially in the top two films on this list.
4. Airheads-
In this film, Sandler plays Pip the pool cleaner, who is also the drummer in The Lone Rangers. While not the best vehicle for Adam Sandler, this is still a great movie that takes advantage of the persona that would eventually comprise the Billy Madison character.
3. Spanglish-
Probably my favorite serious acting performance by Sandler. This film seems to be full of real people and it does a good job of trying to tell a multicultural story in the heart of the region that depends on it the most. One of the few Sandler films that actually deals with pain and you can't help but feel that his performance is the primary influence that really brings it home to the viewer.
2. Happy Gilmore-
What can you say about this one. It is very funny, the characters are memorable, and the action is frantic. There are too many memorable parts in this one to count. I can't believe that so many good actors were able to find ways to be funny in a relatively simple film.
1. Billy Madison-
To be completely honest, there are parts in the first half of this film that I find so annoying that I almost can't stand it. There are other parts that are simply comedic genius. The line after his teacher tells the story of the puppy and the exchange between Madison and the bus driver (Chris Farley) are some of the funniest things that I have ever seen. This film is completely lowbrow, but it is also the film that gained Sandler his first following and will probably stay relevant and funny for quite some time.
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