The 15 best Adam Sandler movies

Before he became a true movie star, Sandler was part of an ensemble comedy. Brendan Fraser is the ostensible lead in this movie about a band of dimwitted guys who take hostages to try and get their music played. Rounding out the band is Steve Buscemi, a future frequent maker of cameos in Sandler’s films. Sandler does right by his friends, you can’t deny that.

This was Sandler’s chance to star in a movie. Look, Billy Madison is dumb. It’s super silly and goofy and not everything works. Having said that, Sandler’s comedic persona was locked in, and the memorable comedy moments have lasted in the lexicon for decades.

In terms of Sandler’s purely silly comedies, Happy Gilmore is the best, and it may not even be close. Sandler’s turn as a failed hockey player turned golfer is one of the best sports comedies — maybe the best sports comedy. Christopher McDonald deserves credit for his performance as the villainous Shooter McGavin, too.

Sandler tends to make raunchy, almost nihilistic comedies. The Wedding Singer dropped him in the romantic comedy world. Yes, a lot of the humor is derived from ‘80s references, but a lot of that is fun. Also, the romantic stuff works, and Sandler deserves some of the credit for that.

Sandler does a lot of business as Bobby Boucher. The accent. The mannerisms. It’s excessive, but it doesn’t tip this movie over into unwatchable. There’s still a lot of fun to be found in his college football comedy.

“Perfectly pleasant” may feel like damning with faint praise, but a lot of movies would love to hit that level. Mr. Deeds, a remake of a classic movie, is perfectly pleasant. You may not laugh as much as with, say, Billy Madison, but you also don’t roll your eyes as much either.

Paul Thomas Anderson, in all his cleverness, decided to take the Sandler comedic persona and see how it played in one of his films. Here, his anger is scary, his emotional stuntedness disconcerting. Sure, it’s also still a romantic comedy, or maybe a romantic drama, but this was the first time Sandler really stretched his legs. Plus, Philip Seymour Hoffman is in it, and Anderson and Hoffman never failed together.

It’s kind of funny that Sandler followed a “What if we took his character’s anger seriously?” film with an “OK, let’s make rage funny again” movie. Of course, Sandler also had quite the costar in Anger Management: none other than acting legend Jack Nicholson.

Sandler reunited with his Wedding Singer costar Drew Barrymore, and the two do have chemistry. Granted, a lot of this movie skates on that chemistry. Plot wise, 50 First Dates leaves a lot to be desired. Also, it has a genuinely disturbing ending that is not recognized as such. Still, among Sandler’s films, it’s still one of the better ones.

Another remake for Sandler, and another sports film. The guy loves sports, and The Longest Yard plays to his interests. It’s a bit less “jokey,” but as far as sports movies goes, it delivers. Sandler isn’t quite as good of an actor as Burt Reynolds, but he does a solid job in his own right.

This is a movie that had been in the works for years, and it finally got made. Of course, it had quite a bit of cache behind it. The movie was written by Sandler, Saturday Night Live and Late Night legend Robert Smigel, and some guy named Judd Apatow. Zohan wasn’t as big of a hit as other Sandler films, but that may be more about the fact the overall quality of his movies had dipped in the new millennium.

Sandler likes to use voices in his performances, so he’s a fitting choice for animation. In the Hotel Transylvania franchise, Sandler voices Dracula. These films are better than they have any right to be. In spite of the broad premise, they are fairly fun.

This is kind of like Noah Baumbach’s version of The Royal Tenenbaums, which is to say it’s more misanthropic and a bit aggravating at times as a result. That being said, Sandler got back into a more dramatic realm, and he got to work with Ben Stiller, Dustin Hoffman, and Emma Thompson. An overlooked entry into the “Serious Sandler” oeuvre.

Sandler’s career for the last several years has just been him making Netflix comedies. Most of them are lackluster. Murder Mystery, though, has some value to it. Sure, Sandler and Jennifer Aniston are on autopilot a bit, but the movie delivers exactly what you expect — and want — from a Sandler comedy called Murder Mystery.

The Safdie Brothers don’t take it easy on the audience. Uncut Gems has basically been classified as a panic attack in film form, and not without justification. Sandler gave an award-winning performance as a diamond merchant who is also a degenerate gambling addict. It’s the most intense work Sandler has ever done, and it will likely go down as his defining dramatic work.