The Wedding Singer (1998)

It could be argued that VH1’s fascination with the 80’s could have been spawned by the popularity of this movie. The Wedding Singer reached an audience that was just old enough to have completely misplaced warm feelings about one of the lamest decades in human history. For about an hour and a half or so, the eighties seems like a cool shindig that we all missed out on. Adam Sandler got to show us his typical brand of funny, as well as flexing his muscle as a musician. Like a lot of his films, The Wedding Singer had a very well developed and directed story behind it, which is why it stands up almost ten years later, like a lot of Sandler’s films.

Reign Over Me (2007)

In an effort to show the considerable acting range that Sandler possesses, this slot was a tossup between Reign Over Me and Punch Drunk Love. It’s been said the comedic actors have a penchant for drama, and in the film Sandler proves this to be true as he presents us with such a complex and tragic character. At no point do you feel like you’re watching Adam Sandler ‘act’, instead he draws us in to the character and the heartbreaking situation that we find him in. This is one of my personal favorite films over all, Sandler or not.

The Waterboy (1998)

What makes actors and actresses with SNL backgrounds so enjoyable in film is their ability to take even the most impossible ideas and strike gold. On its face, who would have thought a movie about a football playing waterboy would be worth seeing? But Sandler and company took a very unlikely idea and had an absolute blast with it. And while that movie probably won’t go down in the annuls of history as the greatest movie ever, it makes me laugh like I’m watching it for the first time, every time.

Mr. Deeds (2002)

It takes a lot of Ballz to remake a Jimmy Stewart movie, and thankfully Adam Sandler isn’t lacking in the cajones department and had no problem remaking Mr. Deeds Goes to Town for a new audience. Sandler was brilliant as Longfellow Deeds, not because of his antics, but because of his ability to work so well with the rest of the cast, John Turturro and Erick Avari where excellent riffing off of Sandler, and the Sandler’s work with Winona Ryder was very convincing, their onscreen chemistry made the movie for me.

Happy Gilmore (1996)

All you have to do is say, “Go to your home… Why don’t you want to go to your home?!?!?” and you will incite immediate laughter. Up there with the first Austin Powers film (another SNL alum) Happy Gilmore made you laugh until you were begging the screen to stop. The movie was jam packed with so many memorable characters and a lot of cool pop culture references. A mix of Caddy Shack meets the Legend of Bagger Vance Adam Sandler is all over the map in this movie, if he’s not getting into a knock down drag out with Bob Barker, he’s chucking Kevin Nealon into a pond. Despite the unrelenting sight gags and one liners, there is still a developed story in the mix, which makes the movie watchable over and over again. I think there is where you’ll really find the key to Mr. Sandler’s success, more so than in Billy Madison, Adam Sandler presented us with a character and a man that we could all cheer for, and through the years, he’s never let us down.

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