The best and worst of Adam Sandler

In the land of entertainment, there are legendary names that are synonymous with the silver screen, names that will be remembered for generations to come for their unparalleled acting, writing, and directing. Then there is Adam Sandler.

One of the most infamous entertainment names of our generation, Adam Sandler has starred in 64 films, has earned 2 billion dollars in the box office, is worth 420 million dollars as of 2020, and has the reputation of being the only actor who can star in four of the worst movies of the year and then make one of the best movies of the year without skipping a beat. His legacy is polarized between some awful comedies, some fantastic comedies, some great dramas, and movies that have made such a cultural impact that they are remembered in greater detail than actual wars, I wish that was a joke.

So I took it upon myself to watch all 64 of Adam Sandler's films and rank the top and bottom 5 of his career so far so that you don't have to, y'know it's fitting I end my journalism career at SJM like this.

So sit back, relax, grab some popcorn, get ya copyrighted Adam Sandler remote from the hit movie Click, because this is going to be a long one, and let's dive into the best and worst of Adam Sandler.

The 5th Best Movie

We start off with Click funnily enough. It was released in 2006 as a comedy and produced by Adam Sandler who also plays the main character in this film. The best way I can describe this movie is that it is filled with a lot of ideas, fails in a good portion of them, but it has a charm in its failure to keeps you watching. There are some legitimately great moments, both emotionally and comically, and this movie has a surprisingly good third act, but then there is everything else. The script is decent at best, plagiarized at worst, for some reason Christopher Walken is here and barely used, and the single longest fart of Adam Sandler's career is in this movie, where Micheal, Adam Sandler's character, froze time and farted on David Hasselhoff. I finished the movie with something akin to a light joy in my heart, but with a slight tinge of regret. As to why this is number 5 on his best movies, besides that this is a very endearing film that rings all of the Adam Sandler bells of "Crazy, stupid, and funny" it was nominated for an Academy Award. the Oscars nominated this movie for best makeup. I don’t know how but Click either did something right or Hollywood went very, very wrong.

The 5th worst movie

Counting off the worst Adam Sandler films is a movie that I do not recommend to anyone above the age of 7. This movie is overall a solid “meh” out of 10 but what solidifies it as one of the worst Adam Sandler films is that Adam Sandler in this film is not good in the slightest. His character is unlikeable and does not mesh well with Adam Sandler’s style of acting, yes I have watched him enough to classify his type of acting, Sandlerian acting if you will, and this movie does not lend itself to that mold of a man acting like child to finally becoming adult. It has flashing lights, really bad references (the jokes themselves are funny but the references kill whatever laugh I could have had), and Kevin James as the president of the United States, that’s it. Do not watch unless you’re with friends trying to make fun of Adam Sandler.

The 4th best movie

Released in 1995, Billy Madison as a whole is objectively pretty average but the defining factors of Adam Sandler are present in an endearing way. Sandler plays a goof-ball, overgrown man child, and despite this character being unlikeable at times (more so than your usual Adam Sandler film), you can tell Adam Sandler as a person is having fun acting out this character and that he is putting on a performance to emphasize an actual moral aimed to his generation of, well, overgrown man-children struggling with finding purpose in life and being functioning members of society. Yes, Adam Sandler played a character with the intent of commentating on society’s changing definition of responsibility and masculinity, I’m just as surprised. It’s strange watching this film, it has no self-awareness whatsoever but yet it feels like it’s communicating a deeper message beneath the layers of corny and goofy humor that ranges from really really good to literally pelting children with dodgeballs, and if that isn’t Adam Sandler, what is?

The 4th worst

Jack and Jill, starring Adam and Sandler

I cannot express to you how much Adam Sandler is in this Adam Sandler film, you see Adam Sandler and Adam Sandler play the two main roles, Adam Sandler as a male named Jack and Adam Sandler as a female named Jill, in a movie produced by Adam Sandler and written with the help of Adam Sandler. There is too much Adam Sandler here, whereas Adam Sandler’s best has Adam Sandler refining himself and improving the quality of Adam Sandler, this Adam Sandler movie focuses on the quantity of Adam Sandler and it gets to be too much Sandler for one Adam to take. It’s too self-aware, Adam Sandler knows too much and uses his Adam Sandler style comedy to Adam Sandler Adam Sandler. Oh yeah, did I mention it also stars AL PACINO? AL PACINO IS IN THIS MOVIE, AND HE DOES A FANTASTIC JOB. WITH ADAM SANDLER. HE CHASES AFTER GIRL ADAM SANDLER, AL PACINO. 2/10, it’s The Godfather of Adam Sandler's career, for better or worse.

The 3rd best

Happy Gilmore, The Wedding Singer, and The Waterboy all have a common thread that makes them great and universally considered "Adam Sandler Classics" It’s Adam Sandler having a decent script (in the case of The Wedding Singer, it’s a full-blown good script) and him acting a character who is allowed to display a wide variety of emotions. I kid you not, when Adam Sandler’s characters are able to showcase some form of empathy, anger, sadness, anything that is not being a comedian, all of the jokes hit so much harder, and Happy Gilmore is a prime example of this. The story is a classic Adam Sandler premise and the characters are surprisingly deep at times, and Sandler expertly plays into Happy, who is the right blend of emotionally charged anger and nuanced zen. Beyond that, the movie is really funny, most, if not all of the jokes land and had me laughing audibly and not just exude air out of my nostrils. I mention the other two movies because they are all of a similar style but with different focuses, The Wedding Singer is a more mature movie with an emphasis on serious themes and less on humor, while The Waterboy is far more comedic than serious, with Happy Gilmore somehow being in between. My ranking of these three movies can change on any given day, but Happy Gilmore strikes the right balance hence its spot at number 3.

The 3rd worst

This movie has all of what makes Adam Sandler, well, Adam Sandler, but there’s also way too much going on surrounding Adam Sandler to make it a good Adam Sandler film. There’s a lot here, both in terms of story and in humor and it certainly isn’t a bad movie but it feels less like an Adam Sandler film and more like a comedian film if that makes any sense. It’s funny for what it is and you can tell the actors had an exceptionally fun time making the movie but it lacks the clarity to really come out of it without anything other than “Man, I wish I had friends and money too.”

The 2nd best

At this point, the two best films should be obvious, but to continue with the suspense, Punch-Drunk Love is a movie where it feels like Adam Sandler stops trying to downplay the idea of emotional vulnerability. After watching all 64 films, I rewatched 5 of them, with Punch-Drunk Love standing out as Adam Sandler’s quiet comedy, if one could even call it that. All of the Adam Sandler tropes are here, don’t get me wrong, but it feels as though Sandler is not trying to play into a gag or a bit to create a laugh but rather he is doing what comes naturally and finds the audience laughing. While the other films on this list have what is essentially the same zany and lively character trying to be an adult, in Punch-Drunk Love, that very same character is now an adult trying to find a reason to be zany and lively. Every aspect of the film objectively is fantastic and is one of Sandler’s best performances from an objective standpoint. Is it as funny as all of the other Adam Sandler films? No, but the range of Sandler's raw acting abilities is shown at what feels to be full, and that alone is enough to make this movie number 2. When observing it within the scope of Adam Sandler’s entire career, it’s an uncut gem in a sea of polished jewelry. It is currently available on HBOMax.

The 2nd and the worst Adam Sandler movie, in no particular order

The Ridiculous 6 and Bulletproof

Do not watch these movies, it is not worth it. There is no joke here, do not watch these films. I didn't want to get the posters for these films because they are that bad. One of them is on Netflix if you really want to watch, but please don't.

The best Adam Sandler movie

After watching 62 movies of Adam Sandler, Uncut Gems was both a massive change of pace from the average Sandlerian style of movie and what feels like a culmination of the morals Adam Sandler has been teaching over the 30 years he had been in the movie business. The movie itself is directed expertly by the Safdie Brothers. It's anxiety-inducing, funny when it needs to be, but tense everywhere else, with a gripping plot and cinematography that keeps your eyes glued to the screen. Adam Sandler plays the role of the annoying gambler, Howard Ratner, exceptionally well. The classic Sandlerian annoying smugness and reserved charm is now a key personality trait rather than a byproduct of Sandler's usual quips, which allows for jokes that don't require a bit to set up and instead can be told while feeling natural to the pacing of the story, which is crucial for this movie in particular. All of these qualities are what make this a great movie, but not why it is the best Adam Sandler film. The reason why it is the best is simple, while the other movies on this list saw Sandler take on a comedy character or archetype, Uncut Gems does something incredibly special. It takes a dramatic, cynical, depressing, annoying, and lonely gambler who goes too far in his selfish desires and made him play Adam Sandler. And somehow this character, who the audience should have no hope for or any sort of positive emotion toward becomes endearing and likable. For that reason, and so many more, it’s a masterpiece. It’s currently on Netflix so please give it a watch.


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