The 10 best Adam Sandler movies, ranked (plus his worst movie ever)

Adam Sandler
Screengrab via YouTube

Funny, silly, ridiculous, stupid, asinine, sincere, sweet, strange – the list of descriptives could probably go on a bit longer.

From the hilarious to the serious to the seriously forgettable, Adam Sandler has shown off his range for more than 30 years now, appearing in nearly 70 films throughout his career. Sandler has garnered critical acclaim and fan praise alike for some of his lovable characters, and for some of his genuine character portrayals.

How can one man make movies with such a tremendous breadth of quality between them?

Is Sandler at his best when he leans into great comedic timing and a stellar supporting cast?

Are Sandler’s serious roles made even more dramatic because we know the bounds of his silliness?

With his wide-ranging deal with Netflix, he’s come to crank out more movies than ever, with quite a few of them feeling a bit unnecessary (though they still seem to get viewership, so what do we know?). With his latest, Hustle, hitting the streaming service recently, Sandler is again showing off his chops — and sports enthusiasm — not long after Uncut Gems received plenty of fanfare for his efforts.

From Happy to Stanley, how many great films has Sandler racked up, both comedy and drama?

Let’s parse through the Sandman’s top 10, with a little gem of a stinker at the end for good measure.

10. Billy Madison (1995)

We almost went with You Don’t Mess With the Zohan here — spoilers, it’s not showing up farther down — but in the end, well the beginning, a star was born with Billy Madison.

This made everything else possible. We had zany antics, great quotables throughout, and Sandler showing his chops could stand up with the most serious and biggest of those already in their craft — Bradley Whitford, Darren McGavin, Bridgette Wilson — while also making them feel comfortable making such a ridiculous movie with him, and seriously making it a great movie. And holy crap isn’t that musical scene above bold, and amazing? How committed is Wilson to her role? It’s phenomenal.

Do you have any more gum?

9. Hustle (2022)

Sandler and sports go well together. He works them into his movies, and even makes movies around them.

At first we couldn’t help but think of Ben Affleck’s The Way Back when we heard Sandler was doing an NBA-themed movie, but this is something else entirely.

Sports fans will really enjoy the movie and its authenticity, while Sandler fans might wish for a bit more from it. It neither goes all-in on his dramatic abilities or his comedic timing, instead straddling the line just a little bit too much. Maybe in time that will actually blend together and the film will shine even more.

The funny thing is, this is more of a movie than anything else. It’s not the drag-your-heart drama of Uncut Gems or Punch-Drunk Love, it’s not the wacky sports with a side of serious stakes like Happy Gilmore or The Waterboy, but it’s just a straight-up good movie — a good sports movie at that — that doesn’t steer out of its lane too much. In that way, it stands out as a Sandler movie, but with his history of great acting, the audience is able to relate to what he and his costars are going through.

8. 50 First Dates (2004)

On the surface, the movie’s trope of falling in love all over again with your partner was put to the literal test, and even though the premise gets right up to the cringey border, it never crosses it.

Not only does Sandler’s Henry Roth eventually find a way to connect with Barrymore’s Lucy Whitmore over and over — and over — again until the end, he finds a sweet way to connect with and win over her understandably protective father, Martin (Blake Clark), and brother, Doug (Sean Astin) to the point that they help him to help her have what we would consider as close to a normal life as possible (married, with children edition).

If you dig too deep, there are some things that don’t add up — like, why doesn’t Lucy freak out even more at the end on the boat — but overall, the movie shows that Sandler and Barrymore’s chemistry can win out and make something seemingly too surreal to enjoy something utterly enjoyable (well, you can skip Blended sadly…two out of three ain’t bad!).

7. Punch-Drunk Love (2002)

Once upon a time, we weren’t aware that Sandler had such intensity inside of him other than yelling and cursing in way that made us laugh.

As a very lonely, haunted, troubled — yet loving and confused — Barry Egan, Sandler sinks and swims with his character as emotions are on full display, sometimes quietly and sometimes maniacally, throughout the movie.

Paul Thomas Anderson does great work with the story, making sure it doesn’t single out Sandler’s character, and the movie isn’t really in the re-watchable category, but it stands as the benchmark that allowed for us, the viewer, to consider and believe that he could be so much more than a slapstick schmuck down on his luck.

6. Funny People (2009)

The almost-serious movie that came in a run of not-so-serious roles for Sandler (we’re not counting Click here), we get the sensitive side of Sandler playing, well, a version of himself but in a way that shows his acting chops.

You get the regular Judd Apatow schtick in here, but the ways that Seth Rogen, Leslie Mann, and Sandler — and even Jonah Hill and Eric Bana — interplay their dialogue and show genuine emotion and softness gives us characters that feel real.

We don’t get to see Sandler in stand-up mode too often even though his original claim to fame is comedy, but here we get into his inner workings in a way that we didn’t in his other roles.

5. Happy Gilmore (1996)

We must admit: It’s tough to discern which was better, Happy Gilmore or Billy Madison, but one stood out over the other on further consideration. Happy has just a bit more soul to it, more oomph, more stakes. And is even more re-watchable.

Whereas Billy is a man-child with a wealth of inheritance at his fingertips if he could just not be so immature and, well, idiotic, Happy is a man without much means who is trying to help save his grandmother from an evil nursing home while proving himself to be more than just a man-child.

The stakes are low yet hilarious for Billy. For Happy, they are a matter of much more, with a better-rounded story, love interest, and a character that — even a little bit — is more relatable.

Ever the sports lover, Sandler somehow made a cool golf movie, and an ultimate sports underdog movie, a comedy and a down-on-his-luck movie, all in one.

4. The Meyerowitz Stories (New and Selected) (2017)

Between the early 2000’s run of more serious roles and approaches, it was about 13 years between truly emotional films from Sandler. Sure, there was some seriousness in there, but from 2004’s Spanglish to Noah Baumbach’s 2017 film — we’re not counting Funny People here — Sandler didn’t fully let us in to his vulnerability and loneliness for quite a while.

Even though it stands as his highest-rated film on Rotten Tomatoes, somehow it feels like not a lot of people gave this one a turn.

Baumbach, whom Sandler asked to create a role for him, does wonders with not just Sandler but also Ben Stiller and Dustin Hoffman as the three men play off each other candidly with touching moments between them.

Sandler has held his own with the biggest names in Hollywood throughout his career, more often bringing them into his realm as he bleeds into theirs just a tad as well (comedically and dramatically). This could definitely stand at the top for the performances alone, but the storyline itself leaves just enough lacking to keep it from the top spot.

3. Uncut Gems (2019)

Somehow, you end up rooting for Sandler’s Howard Menzel even though you can clearly see that he’s a philanderer who not just cheats on his wife — and by extension, his family — but sets out to become rich with his adulteress with a plan to leave said family behind.

He puts himself in positions that seem cringy, and yet here he is pulling them off and getting us to root for it to even pay off and for him to escape harm’s way.

Using a scheme involving a magic rock, former NBA player Kevin Garnett, and an NBA championship ring that doesn’t belong to him that he parlays into collateral, against all odds Menzel’s gamble pays off to get him out of debt and trouble –which he is in because of said gambling and egotistical behavior.

On the precipice of escaping after his succession of parlays pays off and his mistress Julia (Julia Fox) collects their money, Howard does not sense that the mobsters he’s trapped in his jewelry shop are no longer concerned with his new winnings and one of them shoots him right in the head before looting the store.

2. The Wedding Singer (1998)

Not a fan of remakes. However, the sincerity for which we feel the bond between the main characters makes this a movie we wouldn’t mind being seen remade. It could be transferred to another era, with a different band, and comedian.

Yet again, when you fall in love with this movie, though, you fall in love with Drew Barrymore and Adam Sandler, their connection, their ability to be quirky and awkward on the same beat, and to sell you on their chemistry.

Recreating that is not easy. They even almost did it for 50 First Dates, which is solid in its own right, but the original Barrymore-Sandler sensation is a standalone classic.

There’s really nothing else like it. And there’s a reason it used to play on loops on basic cable back when that was a thing, and you could jump in at any moment and watch the rest.  

1. Big Daddy (1999)

The first film in which we saw Sandler really go toward his serious side.

The basis still features him being the funny guy, the immature one, yet he learns to be emotionally more stable and how to round himself — and his acting — into adulthood here.

There are truly tender moments as he tries to connect with a kid, Julian (Dylan and Cole Sprouse), while still showing he’s a bit of an emotional child himself.

By the end, fans of Sandler’s earlier work actually care about him and what will happen to him beyond the question of whether he’ll pull off whatever ridiculousness he is trying for. Here, we want him to pull it off in order to have a better life not just for himself, with a real premise and real stakes at the heart of it all. Even Jon Stewart is great in the movie.

Some might say his best acting came in Punch-Drunk Love or Uncut Gems, and perhaps what came of his career following this film gives it a nudge up the list for us, but from start to finish, this is the most real fun we had rooting for Sandler that didn’t involve him playing a caricature (even if it was a great one, like in The Wedding Singer).

The Sandler stinker: Jack & Jill (2011)

This was a tough one. As great as the great Sandman movies are, yeesh there are some bad ones.

His voice in Little Nicky (and yeah, everything else about it) is not compelling in the slightest. The Do Over, I Now Pronounce You Chuck and Larry, Zookeeper, there is plenty to mine from here, but nearly every actor that is prolific enough puts out some stinkers.

Rarely, though, do they somehow put forward two terrible things in one package.

There’s just no way anyone out there wants to watch Sandler in a wig playing a female version of himself. Trying to re-watch is not possible.

Somehow, Sandler got Al Pacino invested in this storyline and got him to commit to the role (but he’s had his share of bad movies too).

The premise is fine enough, but there is no chemistry between Sandler’s Jack Sadelstein and his wife Erin (Katie Holmes), or with Sandler’s Jill Sadelstein and Pacino (playing a version of himself, going meta). There are no redeeming qualities, no standout performances, you’re only left being distracted asking why Sandler decided to play his own twin sister, so you don’t even really notice the storyline going on of family and, and, umm, nope, you just can’t fathom how Sandler thought this particular schtick and gimmick would work. For a Saturday Night Live skit? Maybe. Full-length feature? Oof.

Whatever is redeemable in Jack & Jill is rendered irredeemable every time Jill shows up on screen, or when Jack tries to be likeable, or, you just keep circling back to the same thing – why?