Jack & Jill
Harrison Ford/MovieStillsDb
Yes, Jack & Jill is making this list.
The internet will tell you this is one of the worst movies ever made. It’s purported to be a film filled with bad special effects and even worse product placement. They are long rants about Sandler’s grating performance as his twin sister, Jill, and critical screeds lamenting Al Pacino having debased himself by featuring so prominently.
This may all well be true. But it is a movie so shamelessly, relentlessly bad that it crosses over the taste horizon and emerges on the other side as a supremely enjoyable way to spend 91 minutes.
And don’t pretend like the “Dunk-acino” sequence isn’t inspired shlock — because it is.
Airheads
Carlito/moviestills
This 1994 comedy is an early entry in the Sandler filmography but is notable as it is one of the few times we see Sandler as a pure supporting act. He is third billed here, alongside Brendan Fraser and Steve Buscemi, but he holds his own as he plays the simple-minded but kind Pip, the drummer of The Lone Rangers who takes over a Los Angeles radio station in a last-ditch effort to get their demo aired.
The movie was a critical and commercial flop, though it did eventually find an audience on cable. The movie also features an excellent soundtrack that is a fun snapshot of a certain 1994 music scene.
The Waterboy
zayne/moviestillsdb
Following the success of Happy Gilmore and Billy Madison, Sandler released two movies in 1998. The first was a film that finally caught the attention of critics and will appear later on this list. The second was The Waterboy, the movie that truly made Adam Sandler into a household name.
Taking inspiration from his “Canteen Boy” character from SNL, Bobby Boucher as a character is another entry into Sandler’s deep bench of figures that are socially inept and overly kind with a deep rage hiding just beneath the surface. The movie is dumb but well-structured and full of plenty of laughs.
Hustle
michaella92/moviestillsdb
In addition to being a big fan of wearing basketball shorts, Adam Sandler is also famously a fan of basketball. It’s genuinely surprising it took until 2022 for Sandler to find himself in a movie that revolves around the sport. In Hustle, Sandler plays a weary NBA coach/scout trying to rebuild his career who then stumbles upon and champions an unknown European basketball talent. There’s a lot here for any NBA fan as it gets into how the sausage is made and features several cameos.
This is arguably the best of the “quiet Sandler” movies. His performance as Stanley Sugarman has a sadness, charm, and relatability that we don’t often get to see. If you have a Netflix subscription it’s a must-see.
Happy Gilmore
Robert McClaine/moviestillsdb
Happy Gilmore built off of the success of Billy Madison, this time adding a sports angle to the mix and an overabundance of product placement — two elements that would play heavily into the rest of Sandler’s filmography.
Sandler is great, but it’s the supporting players elevating this film. The late Carl Weathers is incredible, as is Christopher McDonald’s turn as the film’s antagonist, Shooter McGavin.
And of course, who could forget the famous Pro-Am scene, where Happy Gilmore and his celebrity partner, the universally beloved Bob Barker come to blows?
This is an excellent snobs vs slobs sports comedy.
Billy Madison
Zayne/moviestillsdb
Billy Madison is a great example of how it can be impossible to trust critics with comedy movies. Looking back at the reviews, it is obvious that most critics simply didn’t get Adam Sandler’s bit. This is a shame because Billy Madison is among the funniest movies of the 1990s.
Here, Sandler’s manchild must go back to school and complete his education, lest his father’s business empire fall into the hands of the dastardly hands of Eric, played by the seriously underrated Bradley Whitford. Norm MacDonald, Chris Farley, and Josh Mostel all turn in hilarious supporting performances, and Bridgette Wilson is incredibly charming as Sandler’s put-upon love interest, Veronica Vaughn.
50 First Dates
zayne/moviestillsdb
50 First Dates succeeds entirely on the overwhelmingly charming on-screen chemistry between Adam Sandler and Drew Barrymore. This time, Sandler is a marine biologist in Hawaii who falls in love with a woman with anterograde amnesia and a quirky familiar wary of letting their daughter’s already challenging life be made more complicated by an interloper.
The only thing holding this movie back from being a true classic is the vestigial “Sandler comedy” crassness that pops up here and there and clashes with the otherwise warm tone of the film. Also, the German assistant character Lucy is borderline in 2024 and could put some viewers off completely
The Wedding Singer
richard3rd/moviestillsdb
The Wedding Singer is the best “Adam Sandler” movie despite not being the best movie starring Adam Sandler (those come next on the list).
This is a perfect romantic comedy and one of the best “80s movies” ever made. As we’ve seen before on the list Sandler and Drew Barrymore have the kind of on-screen chemistry that movie studios dream of. The movie is light on the crass, gross-out jokes that bog down 50 First Dates, and is one of the few movies in Sandler’s filmography that take advantage of the man’s musical talents (which is pretty bonkers when you think about it). It’s a total triumph.
Uncut Gems
michaella92/movestillsdb
Uncut Gems is a wild, wild ride. This Safdie brothers thriller is relentlessly paced and anxiety-inducing, throwing Adam Sandler’s Howard Ratner into self-made bad situation after self-made bad situation. Sandler is incredible here, playing a gambling addict jewelry dealer who is white-knuckling through life and caught in a tailspin. It is criminal that he didn’t even get a nomination for Best Actor at that year’s Academy Awards.
The ending is unforgettable, though that undersells the fact that so is the rest of the film. It’s a shame this film didn’t do better at the box office, though it may be too bleak to have broader appeal. Still, the movie is stunning and one of the best of 2019.
Punch-Drunk Love
CaptainOT/moviestillsdb
Punch-Drunk Love is a masterpiece. It’s one of the most beautifully shot and blocked films of all time, with a brilliant score and wonderful performances.
The movie is essentially a deconstruction not only of Adam Sandler-style romantic comedies but also of the characters that Sandler typically plays. Here, he’s still a socially inept, kind-hearted man with unaddressed rage issues that we’ve seen time and again, but this time the movie unpacks the how and why of such a character instead of simply mining it for comedy.
You can tell that director Paul Thomas Anderson has a deep appreciation for Sandler’s other films and his talents, as this is both an elevated take on them and a love letter to them.
