The Five Best Adam Sandler Movies of His Entire Career

Billy Madison

It has to be said that throughout his career that Adam Sandler did hit a lot of the same notes and eventually it was noticed by a lot of people since he was the man-child that didn’t seem to want to grow up. But as time went on he did change his tune and he started showing that he could in fact become a better actor and someone that didn’t rely on gimmicks and one-liners as much as he did when he was still considered an SNL great and a rather comical actor. He’s grown up quite a bit since those days and to be honest he’s someone that might not be considered to be Oscar-worthy much of the time but is still a lot more fun to watch now that he’s taken on a different level in his acting. But then again, you can’t deny that some of his best stuff came when he was younger and still possessed of a very twisted sense of humor that was, and I’m using Stephen King for the metaphor, about on par with a grade-schooler with a good to fair collection of Garbage Pail Kids.

Here are a few of the best movies of his career.

5. Reign Over Me

Anyone that expected this to be in any way comical obviously didn’t watch the trailer since there was no intention of this being a funny movie considering the subject matter. Sandler plays a man that lost his wife, daughters, and even his dog during the 9/11 attacks, and as a result the trauma sent him into a depression so deep that he shut everyone out and simply forgot a good chunk of his life as he tried to shut out the pain. When an old college roommate happens to see him on the street though the two eventually get to connect and he finds out that Sandler’s character is well and truly messed up and seems to have no way to reconnect with the world around him. It’s a very tragic story that shows that Sandler has grown in a big way as an actor.

4. Big Daddy

This felt like one of the transition points in Sandler’s career since the movie had a good bit of comedy in it but wasn’t so overwhelmed by the humor that you missed the opportunity for Sandler to show that he was growing up when it came to his career. The dynamic between Sonny and Julian showed how much the actor had come around to the idea that his time as the man-child was over and it was now time to accept adult responsibilities and do his bit when it came to being the grown-up in the room. The story was overall nice and offered a great deal of comedy as well as touching sentiment since when it comes to adopting a child there’s nothing greater for the kid, but it does have to be done in the right way.

3. The Wedding Singer

This is another transition point in his career but it was one of the earlier ones in which he was still allowed to get a bit crazy and out of control while at the same time showing a more sensitive and sentimental side to his character. He and Drew Barrymore worked great together for this and other movies and have made a great couple on screen. What was so funny and great at the same time about this movie was the fact that back in the 80s, as now even, people didn’t think things were bound to change since they liked them just the way they were. Imagine thinking that VHS would never go out and CD’s would be the wave of the future. Well, they were for a short time.

2. Billy Madison

Okay, this was just crazy time since the sentiment was kept to a minimum and the nuttiness was allowed to roam without a tether or lead, and people loved it. This was back when Sandler was still more of an SNL talent and had yet to fully break into the mainstream movie scene. But Billy Madison did manage to allow him to catapult his way into the big time since it was funny, had a host of characters and famous actors that people wanted to see, and was just flat out nuts since it was about a young man that took nothing seriously and yet still wanted all the responsibility that came with running the family business.

1. Happy Gilmore

No matter what anyone says this is the movie that put Sandler on the map since quite honestly it established him as a serious actor and a comedian that could cross the line between comedy and romance, kind of. Plus the fight with Bob Barker was just classic since how often do you get to see a full-on brawl with an aging game show host? That, and Happy did to golf what only Robin Williams has been able to do, he brought it down to the level of those that didn’t fully understand it in the most amusing way possible.

Yes, Adam Sandler has become a truly rounded actor.

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