The best & worst movies in Adam Sandler's filmography

To call “Billy Madison” a “good” movie is perhaps a stretch. It is, however, a funny movie, and it is the mission statement of the Adam Sandler Comedy. This is his debut as a lead, and “Billy Madison” is fully indebted to the Sandler persona and to the Sandler tone. Truly stupid jokes mixed with sometimes-clunky moments of sincerity. Billy is a deranged character. This movie barely makes sense. But if you like Sandler, you probably love this movie. If you tolerate Sandler, you can enjoy it.

Now, there is no caveat and no framing that can save “Little Nicky.” The decline was already on the way for Sandler, but “Little Nicky” was a derailment. This film is unbearable. Not funny, but also annoying. Sandler disappeared too far into his schtick, and “Little Nicky” ended up wholly a fiasco.

In terms of Adam Sandler Comedies, “Happy Gilmore” is the best of the bunch. It sands off the rough edges of “Billy Madison” into something less polarizing. The trappings of the sports movie may have helped keep “Happy Gilmore” on track. The movie works as a movie, but it is also a vehicle for a less-aggressive version of Sandler, which is weird to say since Happy tries to fight Bob Barker.

While we’re largely moving chronologically, we opened with “Little Nicky” because of how terrible it is and saved “Bulletproof” to pair with “Happy Gilmore.” Both of these movies came out in 1996. One is a Sandler vehicle that allows him to play a broad, but funny, character and works as a classic underdog sports movie. “Bulletproof” is an utterly forgotten buddy cop movie starring Sandler and Damon Wayans. Admit it, you probably didn’t know that Sandler and Wayans starred in a movie together. Even director Ernest Dickinson said of making “Bulletproof”: “I'd like to just erase that whole experience.”

The start of Sandler’s comedy career saw him playing loud, brash doofuses, even if they are well-meaning doofuses. They are out-and-out comedies. “The Wedding Singer” is a romantic comedy, which means Sandler had to work as a viable love interest. And, somehow, he did. Drew Barrymore was also just getting her career back on track, and after “The Wedding Singer,” the two would join forces a couple of other times. The best thing we can say is those movies neither qualified as one of the best nor one of the worst Sandler movies.

With “The Chanukah Song,” Sandler created perhaps the definitive bit of Chanukah pop culture. “Eight Crazy Nights” was his attempt to make an animated Chanukah movie to mix right in with the Christmas fare. Unfortunately, it would be better to have a zero-movie Chanukah canon than to include “Eight Crazy Nights.” It’s the bad version of “adult animation,” all attempts to be raunchy and no attempts to be funny or interesting.

This is the first time stepping outside the Sandler milieu, aside from “Bulletproof,” we guess. The same year as “Eight Crazy Nights” and the wholly mediocre “Mr. Deeds,” acclaimed director Paul Thomas Anderson cast Sandler in the lead of his movie “Punch-Drunk Love.” Anderson realized if Sandler tweaked his comedic rage a hair or two, it could become generally alarming. The film isn’t top-tier PTA, but it’s also arguably the best movie that Sandler is in. Chalk that up to how good Anderson is as a director.

Unfortunately, by “Click,” Sandler had leaned too far into the sappiness. His movies used to be a lot of comedy and a bit of clunky sentiment. “Click,” which wastes the premise of Sandler having a remote control for the world around him, is a bit of comedy and a lot of clunky sentiment. It’s not even annoying, just dull and eye-roll inducing.

Sandler is fully back in “being angry in a funny way” mode the year after “Punch-Drunk Love.” However, “Anger Management” was picked up a notch by the fact that Sandler was paired with a notable actor. That would be Jack Nicholson. You know, one of the best actors to ever live?

Alas, once Sandler became a huge success, he wasn’t making many movies with the likes of Nicholson because he was too busy making movies with his less-talented (sometimes untalented) buddies. Kevin James, a mediocre sitcom actor, owes much of his movie career to being friends with Sandler. “I Now Pronounce You Chuck & Larry” is about Sandler and James as straight men pretending to be a gay couple for insurance purposes. That’s all you really need to know.

Owing to a bad run of movies, “Zohan” almost flew under the radar, even with a name like “You Don’t Mess with the Zohan.” However, this action-comedy saw Sandler team up with Robert Smigel and Judd Apatow to write the script for this film. Maybe because this is the best live-action Sandler Movie in the span of over a decade, we’re overrating it, but it stands out from the fray.

“Grown Ups” is annoying. Not just because it’s a low-quality film, which it is. It’s because it’s the laziest, most self-indulgent thing Sandler could do. “Grown Ups” is just Sandler hanging out with his friends. Seriously, it’s a movie about characters played by Sandler, James, Rob Schneider, David Spade, and Chris Rock who are friends and who have a fun weekend at a lake house. This is when people first really started asking, “Does Sandler just make movies as an excuse to hang out with his friends and family and go to places he wants to go?” It does appear the answer to that is “yes,” at least some of the time.

Sure, “Hotel Transylvania” is Sandler and his friends voicing famous movie monsters, but at least it has some oomph to it. Sandler’s take on Count Dracula is broad, but it’s animation and it’s comedy, so it works. Plus, the first “Hotel Transylvania” (and the first two sequels) are directed by Genndy Tartakovsky, who creates compelling visuals.

Ugh. Going through Sandler’s filmographies leaves you sorting through a lot of dicey outings, but “That’s My Boy” is the one that elicited an “ugh” from us. It’s so bad, and had it ended Andy Samberg’s movie career, we would have accepted it as the cost of doing business. Nobody should have escaped being in “That’s My Boy” unscathed. That includes you, Oscar winner Susan Sarandon!

Noah Baumbach isn’t on PTA’s level as a filmmaker, but he makes critically acclaimed fare more of the prestige variety than the silly comedy variety. He’s another “serious” filmmaker who has embraced Sandler’s acting chops. This time around, Sandler’s character isn’t even just a riff on his persona put in a different, more dramatic context. Sandler had to stretch his acting range for this family dramedy, and he rightfully earned praise for his performance.

The year after “The Cobbler” came out, “Spotlight” came out. It won Best Picture at the Oscars. Why mention that searing drama alongside this asinine slice of magical realism? Because both movies were written and directed by Tom McCarthy. Sandler plays a cobbler who, by putting people’s shoes on, takes their form, not unlike a shapeshifting alien. That allows him to, heavy sigh, walk a mile in their shoes.

As you will see, “Murder Mystery” came out in the midst of Sandler’s deal with Netflix. Several of the movies remaining on this list are Netflix offerings. Most of his Netflix comedies are poor to bad. In fact, every live-action comedy he made for Netflix outside the “Murder Mystery” movies isn’t worth watching. This mystery comedy, which pairs Sandler with former co-star Jennifer Aniston, works as a breezy, B-minus movie. You know, Netflix fare.

This was Sandler’s first film in his Netflix deal, and his first Western. It was a worrying portent of how the deal would turn out. At least Sandler’s cronies, aside from Schneider, were relegated to tertiary roles and cameos. Unfortunately, instead of Sandler’s men-on-a-mission movie, paired him with the likes of Taylor Lautner and Jorge Garcia. That wasn’t much better.

There was legitimate thought that Sandler could earn an Oscar nomination for “Uncut Gems.” That’s how well-received the movie and his performance were. Maybe “Uncut Gems” was just too much for some people. Sandler played a jeweler whose gambling addiction threatens to destroy, or even take, his life. Directed by the Safdie brothers, some have likened “Uncut Gems” to a film-length anxiety attack. To some, this made it one of the best movies of 2019. To others, it was too much. We’re more the former than the latter, clearly.

Then, right in the wake of “Uncut Gems,” Sandler went old school and played a goofy character with a lot of business to him in a silly comedy. Now, “Hubie Halloween” is, in a vacuum, better than a couple Sandler Netflix comedies we didn’t mention. A lot of that is owed to the fact this is a Halloween movie, though. It got to benefit from the trappings of Halloween, and of the horror-comedy genre. However, “Hubie Halloween” mostly squandered all that, making it a frustrating offering.

Now, this time, a Sandler movie got to benefit from the trappings of the NBA. The movie had the rights to use actual NBA team names and logos. It got to be set in the world of the NBA. That’s good for a film about a down-on-his-luck scout. We didn’t have to deal with a bunch of fake teams and logos and stuff. A bunch of players and coaches appear as themselves. This time around, though, all this wasn’t squandered. While “Hustle” is labeled a dramedy, it’s more dramatic than comedic, but that is part of what makes it work.

We’ve saved “Jack and Jill” for the last of the bad movies because it is just so bizarre and stands as a testament to the creative nadir Sandler hit. Okay, and also somehow we accidentally forgot to include it originally but knew we had to have it be on the list. You can’t talk the worst of Sandler and not include “Jack and Jill.” You probably know this is the movie where Sandler plays the titular twins, including the incredibly broad Jill. You may know it as the film where Al Pacino, the Al Pacino, raps about Dunkin’ Donuts. While you can’t accuse Sandler of phoning it in, you also can’t accuse Eddie Murphy of phoning in “Norbit.” That doesn’t make things better.

It’s always preferable to end on a good note if you can, and fortunately, we can. This animated movie, which is a true Sandler-and-Smigel collaboration, was surprisingly well-received. Sandler voices the titular Leo, a 74-year-old lizard who lives his life as a classroom pet. It’s family-friendly with a bit of envelope pushing (within reason). It’s sentimental without being saccharine. Plus, the animation looks pretty good. Sandler may just be doing a voice, but he is doing a voice, which is to say, he is acting. “Leo” stands as Sandler’s best Netflix comedy, even if it is animated and about a lizard.