You don’t mess with the Sandman. Illustration: Jaya Nicely

How do you reckon with a career as polarizing as Adam Sandler’s? If you account for inflation, the 53-year-old zhlubbyman comic actor has starred in 18 movies that have each grossed more than $100 million worldwide, beginning in 1995 with Billy Madison. That’s more than Ben Stiller; more than Jim Carrey; more than Will Smith; more than Tom Cruise. In the same time period, only two movies that he’s starred in and produced have received higher than a 50 percent score on Rotten Tomatoes — Happy Gilmore and The Wedding Singer (though both are inflated by extremely positive DVD reviews). Sandler, who in 2019 marks 30 years of making movies, has 11 Razzie nominations for Worst Actor and 11 acting nominations from the People’s Choice Awards. It’s the dichotomy that has followed Sandler is whole career: The critics hate him, but audiences love him.

This split arguably stems from the type of movies Sandler chooses to make — big dumb comedies. Film critics are in the business of being (and seeming) smart, and that is at odds with Sandler’s intent as a filmmaker. That disconnect isn’t unique to Sandler — from the Three Stooges to Jerry Lewis to Mel Brooks to Jim Carrey (save Liar Liar, oddly enough) to MacGruber, there’s been a lot of great comedic work beloved by many but not by reviewers at the time of release. The difference is that when Sandler makes (as in, stars in and produces) a movie, it’s exclusively big and dumb. Though I clearly disagree with the critical consensus on specific movies, I wouldn’t say they are constantly wrong. (I also wouldn’t say the popular opinion is constantly right; this is not a list in order of box-office gross.) Film critics are judging Adam Sandler’s movies against every movie; this list is about judging against themselves.

The thing I ultimately came back to when approaching this list is that Sandler has had an unprecedented amount of control over the movies he has made. Excluding some early work and the straight acting gigs with more serious directors, Sandler has written or rewritten essentially every movie he’s been in (though he often doesn’t take a writing credit) and served as an executive producer on all of them since The Waterboy. Since The Wedding Singer, he’s hand-picked the directors (and often, according to an interview with Norm Macdonald, essentially co-directed). He’s worked with the same few guys over and over — Frank Coraci, Steven Brill, and Dennis Dugan have combined to direct 17 Sandler films — and he’s famously, and increasingly over time, filled the cast with friends and past collaborators. He’s never had to waver from this approach because of his continued success. And right when it seemed like things were taking a dip, with four sub–$100 million grossers in five years, between 2011 and 2015, he signed a four-picture deal with Netflix that turned into an eight-picture deal that let him continue with even more freedom. As a result, when he does appear in other people’s movies, it’s not part of an attempt to raise his status in Hollywood, since he already gets to do whatever he wants. It’s driven by a desire to push himself, to try something new, to make new friends, to never stop working.

The point is that Sandler only makes the movies he intends on making. As he put it in The Independent, “I didn’t get into movies to please the critics. I got into it to make people laugh and have fun with my friends.” So if you watch all of his movies in a row, which I did, you can tell they come from the same point of view, which can also be found in his five beloved studio albums and his ironically acclaimed Netflix special 100% Fresh. All share core themes, structures, and character types with an Adam Sandler movie — a sensitive, quick-tempered, Gen-X man-child hero journeys to adulthood — and more specifically manhood — defeating bullies, meeting silly characters (as a way of showcasing his friends), and learning a lesson (one that’s transferable to his audience) along the way. Over the last decade or so, there have been exceptions, as Sandler got older, married, and had kids. The archetype was adult but still trying to get better, now often with the goal of being a better partner or father. Almost all of his serious work has served to subvert and/or complicate his fundamental character types.

As a result, when considering his oeuvre, I tried to judge his works by how successfully they achieved what he has been trying to do his whole career. That means artistically superior movies, like a Meyerowitz Stories, will be ranked lower than movies like The Waterboy, which better articulates Sandler’s artistic point of view; on the other hand, you’ll find Meyerowitz still higher than Sandler comedies like Little Nicky, since Meyerowitz represents a culmination of his acting life. It’s a balance.

To assemble this list, I watched every Sandler movie again, in chronological order, in order to note his evolution and to overcome bias toward movies I saw when I was younger. Only movies in which Sandler is one of the top-three billed actors were included, which excludes the cameos he did as favors to his buddies in, for example, The Animal and Top Five and a fairly small part in Mixed Nuts. Watching them all, you quickly get a sense of what is important to Sandler, and I endeavored to rank the films based on the criteria Sandler seems to value. I tried to forgive, though not overlook, his movies’ faults, whether they be bad jokes, clunky cameos, or whatever Rob Schneider was doing, because they are part of what it means for something to be an Adam Sandler movie. It’s not about being a contrarian but treating the project as a thought experiment that presupposes Adam Sandler movies aren’t necessarily “bad” — so if there is no objective standard of quality, which would be the best?

This is not a curve. This is a ranking of the best Adam Sandler movies, as opposed to Adam Sandler’s best movies — that would imply a universal value, which I reject; this is about relative value. I ranked Sandler’s movies not by which was the best movie (again, whatever that means!) but by which was the best at being an Adam Sandler movie. And, as you already know, since you looked before you read this intro, Click is No. 1.

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41-31 T h e B o t t o m

41. Going Overboard (1989)

Adam’s first movie … if you can even call it a movie.

To put it mildly: Sandler’s first film, released a year after he graduated from NYU, is an unwatchable piece of shit. I was going to put some late-era Sandler film on here to make some point, but I wouldn’t wish watching Going Overboard on my worst enemy (you know who you are). In it, Sandler plays an aspiring comedian who gets a job working as a waiter on a cruise ship filled with beauty-pageant contestants. Considering it’s obscurity, and the fact that seemingly everyone involved in it is embarrassed by it, there’s not much information out, but the story goes the ship was already set to transport Miss Universe Pageant contestants and a no-budget movie was built around that fact.

Not only is the film amateurish — the crew forgot to bring the box of lenses, so the cinematographer was forced to shoot with the wrong equipment — Sandler’s performance is hardly a diamond in the rough. It’s just rough. His sweetness and sensitivity are nowhere to be found in his goofy, charmless performance. Regardless of quality, it was clearly a fun time, what with it being an active cruise ship filled with Miss Universe contestants an all. Sandler has told fond stories of getting to work with Milton Berle, and it set the precedent of Sandler working with his friends. Allen Covert, a college buddy, appears alongside Adam, kicking off a long history of collaboration. And it was on this set that he met Steven Brill, who would go on to direct Sandler’s Netflix special, 100% Fresh, as well as many of his movies, including Little Nicky, Sandy Wexler, and the upcoming Hubie Halloween. It was also the start of a now-decades-long friendship with director Peter Berg. No matter the quality of the product, Sandler learned that making movies could, and should, be a good time.

Adam’s worst collaboration with an acclaimed director.

Photo: Image Entertainment

On paper, The Cobbler sure sounds like an Adam Sandler movie: After losing his father, a New York cobbler decides to get his life together and tries to find his purpose by magically turning into his customers, which he does by literally walking in their shoes. However, writer-director Tom McCarthy’s script would have benefited from a Sandler rewrite, as he is known to do on Happy Madison pictures, to lighten the heavy-handedness of the message with some good ol’ fart jokes. Instead, it landed as a tone-deaf slog. Not all of Sandler’s more serious films are great, but he tends to do a good job in them. The Cobbler is the exception. The Cobbler is a bad movie that Sandler is bad in. It doesn’t help that he isn’t even in the thing that much, since much of the work is done by actors like Method Man playing Sandler’s character while he’s wearing someone else’s shoes. On top of that, Sandler (who was born in Brooklyn but raised in New Hampshire) has struggled through much of his career to figure out how to play a real New Yawk–y guy in a way that feels genuine; this is one of many stumbles on his way to better, more stripped-down attempts at nailing that character type.

39. Bulletproof (1996)

An opportunity missed.*

When Damon Wayans hosted SNL in 1994, Sandler suggested they do an action comedy together. Not too long after, he sent Wayans the script for what would become Bulletproof. It makes sense. You can see them as a mismatched pair: Wayans as a charming, competent undercover cop and Sandler as a sweet, dim small-time crook who turns on the kingpin/comedic foil. And there are glimpses of that in the finished product, as Sandler is quite likable as a guy in over his head. Still, Bulletproof suffers from a problem that’ll hamper much of Sandler’s work: its rating. Despite recording the absolute filthiest comedy albums, when it came to his pre-Netflix movies (it’s hard to pinpoint some of the Netflix offerings’ ratings since many don’t have MPAA designations, but they lean raunchy), Sandler almost exclusively worked in PG-13, as was the fashion when he was in his prime. Bulletproof is an extreme example of this, as it was written and shown as an R but then, according to the film’s director, Ernest Dickerson, he was asked by the studio to “cut it as close to a PG-13 as you can get.” So, sure, the film has a little more cursing than much of the list, but it is still just missing something. As Dickerson is said to have put it: “The movie was castrated.” If anything, it was useful for Sandler to get more experience on-camera, shaking off some of the discomfort you can see in Happy Gilmore, which came out earlier that year. Considering what came next — the run of Wedding Singer to Waterboy to Big Daddy, which turned him into a movie star — Bulletproof seems less of a setback than a learning experience.

At some point, you get too old to play a man-child.

A couple years ago, I wrote about how there is an ideal age for a comedian’s persona. To use a Happy Madison–verse example, Rodney Dangerfield famously needed to be an old guy before a large audience got him. Watching Pixels — a movie in which Sandler and a band of former ’80s arcade savants have to put their childhood gamer chops to the test to defeat an invading alien army that’s taken the form of vintage video-game characters — I was reminded of one specific passage of the piece: “If Marc Maron were a character in a play, what age would Marc Maron, the human being, be most believable in the role?” Pixels came out a couple months before Sandler turned 49, and it is instantly clear he is no longer believable, or even watchable, as the classic Adam Sandler character.

Beginning with Billy Madison, Sandler had been in a Groundhog Day–like cycle of playing versions of the same man-child. That character wasn’t stuck in his college days in the manner of the man-children who composed the so-called Frat Pack in the aughts (Will Ferrell, Vince Vaughn, et al.); Sandler was too much of a “regular” guy to be seen as collegiate. His sweet face, mixed with a juvenile sense of humor and social life (his early characters tended to party less and have less sex than your typical comedic protagonist), made him more of an adolescent boy, mixed with a touch of “little baby.” This character, at the start of a given movie, failed to grow past that point, often living as an underemployed slob. The movie would become a little hero’s journey, where he emerges by the end a better, more healthy member of society. (Starting in 2003 with Anger Management, this type of Sandler character had a career but usually wasn’t doing well in it and had to grow up in a different way.)

Sandler’s movies depend on you caring about his character because they’re played by your pal Adam Sandler. (This often puts his movies behind the eight ball with critics, who may go into the movies disliking him.) They depend on goodwill, but by 2015, at the age of 48, it’s hard to root for him as another zhlub with arrested development. Where once you sympathized with his characters, now their belief in that they deserve better feels almost like entitlement, as is it does in Pixels. The movie itself, stupid as it is, looks cool, but it ends up be just so damn boring because you don’t give a shit what happens to Sandler’s character. There’s a natural fatigue to this type of story for him. It’s probably no mistake he hasn’t done one like it since.

37. The Longest Yard (2005)

Sandler wears this rare turn as a high-status character like an ill-fitting suit.

In most of his comedies, Sandler’s usual range is either “sad losers” or “regular guys who are also sad.” Only on rare occasions (Just Go With It, Don’t Mess With the Zohan) has he tried his hand as tough and/or cool guys. It’s always an awkward fit, since he doesn’t do high status well, but it was never more egregious than in The Longest Yard. Seven years after playing a sensitive Cajun idiot savant who only knows how to tackle hard in The Waterboy, he cast himself in this remake of the classic Burt Reynolds film as a sarcastic, hard-partying, elite former professional quarterback who can handle himself in jail. You can call Adam Sandler a lot of things, but “a Burt Reynolds type” is not one of them.

Watching it now, it feels more like a Vince Vaughn movie that Sandler ended up making simply because he likes sports. The supporting cast does little to support, since it’s filled with professional football players and wrestlers who are asked to shoulder large parts of the comedy, which they simply can’t. Naturally, and unfortunately, some of these big, strong men — like Michael Irvin, Bill Romanowski, Steve Austin — went on to become Sandler-verse regulars (though Terry Crews would go on to to be a fantastic addition to the stable). At least Chris Rock is pretty funny in it.

36. Just Go With It (2011)

His most frustrating, least lovable romantic comedy, co-starring Jennifer Aniston.

Photo: Columbia Pictures

While romance is only occasionally at the center of Sandler’s plots, there does tend to be a relationship in all of them. In almost all of these movies, he and his love interest fall for each other immediately. (It’s often positioned that they are the only women who would be into Sandler, rather than that he is irresistible.) What inevitably gets in the way of their love is that his character needs to work on some fundamental thing in order to grow up, and that’s what the entire plot revolves around. The women tend to be more mature, evolved, functional, and in the position often of helping Sandler’s character on his journey. As you might expect, some of these female characters can feel less like characters and more like prizes for growing up, especially in early films like Billy Madison and Happy Gilmore (and arguably even in Anger Management). But this approach is not without its merits: The dynamic means there typically isn’t a power imbalance that favors Sandler’s character, and the women are never positioned as antagonists — there are typically no “annoying girlfriends” spoiling all the fun.

Just Go With It is the opposite. Adam Sandler plays a successful plastic surgeon and Jennifer Aniston his assistant. Despite their relationship being at the center of the movie, the plot is set up so Aniston’s character passive-aggressively tries to spoil Sandler’s big lie to Brooklyn Decker (which is that Aniston’s character is actually his ex-wife and her kids are his). Whatever the relative merits of the enemy-to-soul-mate rom-com structure, it is not only poorly done here but also feels out of step in Sandler’s work. The result is maybe the most generic film Sandler ever produced — and Sandler and Aniston do not have the chemistry here to save it.

Though the film oddly lacks much Sandler, it does reveal a lot about what is important to him.

If you don’t like Adam Sandler, Mr. Deeds is a more watchable movie than many of the films ranked above it. That’s because there is so little Adam Sandler in it. Yeah, he is the star of the thing, appearing in most of the scenes, but he isn’t tasked with carrying much of the comedic load, and his titular Mr. Deeds doesn’t really have an arc — Winona Ryder’s character is the one that goes on the Sandler-esque journey to adulthood. Mr. Deeds is ultimately an exceedingly boring movie, but it does have a value in understanding what I believe are the two biggest misconceptions of Adam Sandler: that he just does it for the money and is lazy.

I understand the money argument, considering how he makes movies for a large audience and his reputation for product placement and that his films are not seen as “art.” But considering the plot of this and other movies (see Grown Ups, The Wedding Singer, Click), you get a sense of a person who is not motivated by making money. If anything, he’s incredibly skeptical but accepting of it. What seems to drive Sandler more than anything else is juice — juice to make the movies he wants to make and work with his friends. On an episode of Norm Macdonald Live, Sandler said he wanted to cast his main buddy from college, Allen Covert, as one of Billy Madison’s drunk friends alongside Macdonald but was denied by the studio because of Covert’s “dead eyes.” That changed when Sandler gained clout: Covert has a huge part in Mr. Deeds, as well as many other Sandler films, and he often served as a producer and/or writer on plenty of Happy Madison projects — sometimes, according to the hacks, to Sony’s dismay.

This phenomenon also feeds into his perceived laziness. He simply makes the movies he wants to make. During an interview with Jason Reitman, who directed Sandler in Men, Women, and Children, a journalist mentioned that it was good to watch Sandler “give a shit” again. Reitman replied that this presumption people have that “Adam Sandler has movies he cares about and movies that he doesn’t” needs to be corrected. I would offer that Sandler is disinterested in trying hard to make a movie that is perceived as “smart” and is sometimes also disinterested in always being the funny part of a movie; he’s satisfied with being the center while his friends do the funny stuff. To be clear, this also isn’t good, but it is more specific than that he’s lazy. In his best movies, he’s funny, and there is also a funny world around him he can interact with. That’s just not the case with Mr. Deeds.

34. I Now Pronounce You Chuck & Larry (2007)

An offensive portrayal of straight people.

Photo: Universal Pictures

Big Daddy, released in 1999, in the wake of President Clinton signing the Defense of Marriage Act, dedicates a surprising amount of time defending gay marriage. It’s not subtle, but it is admirable, considering Sandler’s target demo: young, male, and the young, male at heart. I Now Pronounce You Chuck & Larry, released in the thick of the gay-marriage debate, takes whatever instinct he had in Big Daddy and pushes it to an extreme. Promoted as a gay-panic farce, Sandler falls just short of looking right into the camera, directly addressing the audience, and telling them what words they shouldn’t say anymore.

Now that that’s out of the way: This movie sucks, and Sandler sucks in it. I understand in principle why he made his character, as Wesley Morris perfectly put in his review, “flamboyantly straight” — to better justify why he’d be so resistant to the idea of marrying his friend in an insurance pinch — but it’s a terrible fit for Sandler. It’s just a bummer. Same for the use of tired gay stereotypes. Again, the joke is supposed to be on how out-of-the-know these two bros are, but the result is that a lot of jokes sound like missed notes. The fact that they bought a Barry Manilow record to seem gay is less offensive than it is very tired.

Sandler is a revelation in a painfully heavy-handed satire.

After Going Overboard, there isn’t a movie I’d be less likely to recommend than the inartful, heaviest-of-handed Men, Women, and Children. God, this movie. It has all the insight of a local-news package on limiting kids’ screen time and the subtlety of a teen being murdered by a computer falling on his head. It’s like if Black Mirror was written by your grandfather.

Despite all of this, in a film made up of a many overlapping, terribly done narratives, Adam Sandler and Rosemarie DeWitt’s story about a married couple who each use different parts of the internet to find people to have affairs with is absolutely lovely. I wish director Jason Reitman had just released a short film of their 20 minutes. Specifically, the film includes two of the best dramatic scenes of Sandler career. The first is his first interaction with a sex worker. Sandler’s more adult roles tend to find ways to put him in situations that bring out the sad, scared-little-kid parts of his persona — this one is not unlike the phone-sex scene in Punch-Drunk Love, both conveying an undeniable sweetness and innocence that thinly covers a deep sadness. More impressive is the final scene (spoiler alert, but who cares), where Sandler confronts his wife after seeing her with another man. Reitman said in an interview that Sandler was “as prepared as any actor [he’s] ever worked with,” ready with questions and thoughts about what the final scene meant. And you can tell. For an actor most often mocked for screaming all the time, the way he underplays the moment is brilliant. Sandler, because of that punim of his, is good at playing bummed, but this scene demanded more shading — anger, charm, cockiness. In a painfully obvious film, Sandler was able to convey something more complicated.

32. Airheads (1994)

The first time Sandler’s charm found its way to the big screen.

Airheads is a watchable movie. Ostensibly a comedy, though not really funny, it’s a perfect movie to watch on cable. Even watching it now, years removed from when rock and roll was king, you can see why it would become the kind of mini cult hit that would air constantly on Comedy Central. Though he had already been quite popular on SNL by this point, Airheads was when some took notice of him as a possible future movie star. Peter Travers, in his review of the film, called Sandler a “red-hot screen find.” In a fairly limited role, you mostly get a taste of sweet, dopey Sandler, gently mumbling and playing anger only as a joke. It’s still early in his acting career, but in certain scenes — like when Steve Buscemi’s character tries to teach him how to be tough — you get a sense of what he’d become.

Ultimately, however, Sandler doesn’t do enough to justify ranking it higher than movies that he’s much more involved in.

31. Bedtime Stories (2008)

The rest of the movie doesn’t live up to Sandler’s turn at playing some stupid little characters.

Photo: Walt Disney Pictures

Bedtime Stories is Sandler’s one and only live-action foray in PG. It’s a surprising fact. Of course, he didn’t need to do it, as he had such tremendous success doing PG-13 comedies and a spattering of prestige pictures, but when you think about it, Sandler just seems like a natural fit for kids’ movies. He’s good with kids, his stories tend to be simple, his comedy involves a good degree of funny faces and farts. And there are moments in Bedtimes Stories, where Sandler does seem like a natural. The movie features a lot of fantasy segments where Sandler gets to play stupid little characters, like a stupid knight, a stupid cowboy, and a stupid spaceman, and it’s cute and he makes funny sounds. The problem is the movie around the fantasy scenes, which has real structural issues that make it hard to care about.

The best Adam Sandler movies — hell, even the worst Adam Sandler movies — start with his character being in an undesirable position because of decisions he’s made, and as a result of making changes in his life, he ends the movie in a better (more grown-up) position. But not Bedtime Stories. Yes, his life is not where he’d like it to be (he is the handyman of a hotel his dad promised him he’d run one day), but there is nothing about his character that put him in the position — his dad sold the hotel and for some reason Sandler’s character then just stuck around. As a result, it’s entirely unclear what we’re supposed to think of this guy and have no reason to care about what happens to him. Maybe it worked for some kids (I mean it clearly worked for some — the thing is one of his highest-grossing films), but compared to his other movies and his only other PG movies — my beloved Hotel Transylvania films — I’d prefer something that sticks with you a bit longer, instead of merely passing the time.

30-21 W A T C H A B L E B U T F L A W E D

30. Reign Over Me (2007)

Adam’s heaviest performance to date (if not ever) suffers from unclear writing.

Sandler admitted in an interview that playing Charlie Fineman, the PTSD-suffering New Yorker who lost his wife and children on 9/11, was the biggest acting challenge of his career to that point, so much so that he initially passed on the part. “I was kind of scared of it,” he told Coming Soon. “I had to just create a guy, and I wasn’t sure I could do it. I was pretty sure on Punch Drunk Love I could do it. When PTA gave me that script and he was telling me about it, it was, ‘Oh, okay, I can do that.’ This movie, every time Mike [Binder] would tell me, ‘Hey, you can do it. You can do it,’ in my head I was like, ‘I don’t know if I can do it. I hope I can do it. I sure want to. I don’t want to let you down.’”

The result was mixed. You can see what writer-director Mike Binder was thinking — to that point, Sandler had made a career out of stunted development and childlike naïveté, so why not subvert that by having the cause of his juvenile behavior be a traumatic event? The issue is that what defines Sandler, maybe more than maybe anything else, as an actor is his sensitivity — be it in heavyhearted sweetness or quick anger — so he isn’t a great fit at playing numb and detached. (Not to mention it’s another failed attempt at a New Yawk accent.) Still, the problems in Sandler’s performance seem ultimately the fault of the uneven script. Sandler does his best — the scene below where he finally talks about what happens is devastating — but it’s often unclear what the parameters of Charlie’s issues are from one scene to the next. It was a noble failure.

29. Grown Ups (2010)

Busyness gets in the way of the fun of seeing friends hang out.

Photo: Columbia Pictures

Ready for this? The problem with Grown Ups is that it was too ambitious. Excluding a two-hander here and there, Sandler mostly made solo-protagonist movies up until this point. He would make plenty of room (sometimes too much) for other people to be funny, but the plot zipped along easily enough. Grown Ups has five dude leads — Sandler, James, Rock, Spade, Schneider — each dealing with their own crisis of masculinity while also giving the film’s central women — Salma Hayek, Maria Bello, and Maya Rudolph, all as wives — arcs and funny scenes of their own. (Why, yes, it does pass the Bechdel Test; a surprising number of Sandler’s films do.) There’s also a whole mess of kids, whose roles in the plot get mired in a heavy dose of when-I-was-your-age-ness. Throw in the greater premise — of how getting together with friends can bring up and lay bare old and new insecurities — and it all just gets too muddled, especially since the point of the movie was to have as much fun making it as possible. It seems they might have succeeded in that goal but failed to convey that joy onscreen.

With all that said, failings aside, it’s clear Sandler learned a great deal from Grown Ups, both in terms of how to make movies like this and what it is he likes about movies like this, as this film marks the beginning of one of the larger shifts of Sandler’s late career: From this point on, Sandler largely stopped making single-protagonist movies, opting instead for ensembles or two-handers (though in Jack & Jill he played both hands). It would take him a few more at-bats before he really nailed his version of big-cast movie. As he got older (especially after starting a family), he became less interested in living and portraying a self-centered life. One of the most enjoyable things about watching and considering all of Sandler’s movies together is, as Norm Macdonald put it, you watch a person grow up.

28. The Ridiculous 6 (2015)

Watch. High.

At this point, every movie from here on out, I’d recommend to a person, depending on the person. For example, take a high person — like, a really high person, so high they forget how to chew gum, just leaving the dry stick in their mouth for a few minutes until they try to eat a pretzel and are like, “Oh, yeah, the gum.” If that person puts on The Ridiculous 6, they will have a nice time. It’s essentially if the fart scene from Blazing Saddles was an entire movie, and it’s kinda really funny at times. It is easily one of Sandler’s most bit-filled movies, with an impressive array of characters (though some performances, most notably Vanilla Ice’s, suck real bad). At times, it feels less like a movie than an assortment of dumb Western-themed sketches — as with the scene where, for some reason, they invent baseball.

This still remains Sandler’s only parody, as Sandler usually prefers to just do the genre itself than do a film that is satirizing the genre. In that regard, there was a real missed opportunity in how the film treated its Native American characters. Knowing that Sandler really doesn’t want to hurt people’s feelings — at SNL, he would tell Norm Macdonald he should be nicer, for (one cute) example — I have to say that the movie still fails in its attempt at making fun of how Native Americans were portrayed in old Westerns. Ultimately, the jokes don’t feel like they pointed at the stereotypes as much as they utilized them. Ethnic humor has been a fixture of the lowbrow for decades, if not centuries. Yes, a lot of it is of the punching-down variety (if not an active form of oppression), but, to this day, you’ll see a lot of what I’d consider punching sideways between ethnic groups. I’m not saying Sandler should “know better” — just that it’s an aspect of lowbrow comedy that doesn’t necessarily fit well into the rest of his generally sweet comedic world. Because it makes up a larger portion here than other of his movies, it’s a failure of execution that brings the whole thing down.

The Sandman gets dirty again.

Another movie in which an Adam Sandler character is stuck in a state of arrested development because of a traumatic experience! Though it’s played a bit differently here than in Reign Over Me. Sure, Sandler’s character is celebrated for sleeping with his teacher when he was in high school, but it’s clear the movie is saying that it messed him up. That part of the character isn’t really addressed head on — the film is more about the father-son relationship — but it does make the whole film a bit sadder than it would be otherwise.

Still, when Sandler fans discuss TMB, it’s about how it represented a return to dirty, dirty form. It’s not nothing. After watching all of Sandler’s films, the PG-13-ness of them becomes frustrating. It was the style of the time, and Sandler obviously had a tremendous amount of success, but for people who listened to his albums, it always felt like part of Sandler’s comedic perspective was missing. In that aspect, That’s My Boy (which originally received an NC-17) feels a bit more swashbuckling. Still, there was further for Sandler to go …

26. The Do-Over (2016)

Sandler’s never been dirtier or looser onscreen, but the movie doesn’t live up to the performance.

This is the “further.” At one point, Sandler gives one of his own fingers a blow job. Then he brings another one of his fingers into the action and gives it a blow job. And he trades back and forth, making some realistic and unrealistic noises. It is very funny and really feels like the Adam Sandler who made all those early albums. Where That’s My Boy was the first Happy Madison picture to get an R-rating from the MPAA, The Do-Over, because it was released on Netflix, wasn’t even shown to the MPAA. This is the closest an Adam Sandler film has felt to the guy who wrote “Medium Pace.” Sandler’s ostensibly playing a cool dude, which on its surface isn’t a great fit, but his performance ends up kind of making sense after the big twist toward the end.

The problem is this movie is very confusing. It takes almost the entire thing before you realize what’s happening — and not in an exciting mystery way but a tonally all-over-the-place way. The other major problem is David Spade is horribly miscast as an ineffectual dweeb. I generally accept that part of Sandler’s thing is using his buddies, but as he shifts later in life to ensemble and buddy comedies, it has really been a drag. Yes, being able to work with friends is clearly part of Sandler’s value system, and the list tries to account from that; however, the issue is when this value hinders others, like making a movie that makes sense.

One of the most and least mature of Sandler’s movies.

When I first saw Blended, I wrote a very personal essay for this site about the very emotional experience I, coming from a blended family myself, had in the theater, because I cried just so, so much. Upon rewatching, however, I’m even more impressed. A nice fit in Sandler’s late-career dad phase, Blended is a love story in which the characters fall in love with the other person for their parenting. This isn’t just a mature storyline for a Sandler movie but for any mainstream comedy. This maturity, however, is surrounded by some of the absolute worst jokes in any Adam Sandler movie. Multiple scenes have some side character turning to camera and saying some incredibly hacky line like “This shit just got real.” Worse yet is the portrayal of the Africans, which multiple critics compared to minstrel shows. It wasn’t all mean-spirited — and Terry Crews is pretty funny as the leader of a Ladysmith Black Mambazo–esque group — but it was definitely stereotypical and uncomfortable.

24. Murder Mystery (2019)

Aniston and Sandler find a winning, natural chemistry.

Photo: Netflix

Murder Mystery is a true two-hander, so much so that the film’s writer speculated that it was the reason the film bounced around in development for so long — the theory being that male actors didn’t want to have a “truly equal part” as their female co-stars. The film, in which Jennifer Aniston and Sandler play a working-class New York married couple that gets caught up in a fancy Agatha Christie–style murder mystery, fits nicely in Sandler’s Netflix slate, which tend to showcase his fellow actors as much as, if not more than, himself. If anything, Murder Mystery shows Sandler taking Aniston’s performance lead. “Every night, we would go back and tweak the scenes,” Aniston said. The director said he wanted it to feel like Sandler and Aniston walked into the wrong movie. That meant the scenes were already heightened, so instead of doing big on big, as Sandler has done in the past and sometimes very successfully (Zohan), he gave one of his most grounded performances in any Happy Madison production. He underplays a lot of the comedy, often throwing away lines instead of leaning into (or outright shouting) jokes as he’s known to do. Aniston and Sandler are both great, and their chemistry is so charming it makes what would be a fine enough movie an absolute delight.

Compare it to Just Go With It, and, man, what a difference eight years makes. In an interview leading up to the release of Murder Mystery, Aniston described the difference between their chemistry in the two films simply: “He is a lot older now.” Watching the film, you know exactly what she means. Just Go With It was not Sandler’s final man-child, but the five or so years that followed, it represented a major shift away from that character and toward something a bit more world-weary and mature. This is not to say his movies necessarily all became more grown up but that the characters he plays in them seem to better reflect the Sandler we started seeing in real life; sweet, glum, awkward, or, as he put it in the same interview, “softer” and “more lovable.” To be fair, these traits were in his earlier performances, but often they’d get overpowered by the angst, rage, and immaturity. His best roles demand all of it. Murder Mystery is not one of Sandler’s best roles — in that it doesn’t ask for full Sandler — but he is exquisite alongside Aniston.

As a whole, Murder Mystery, a celebration of marriage as partnership, fits nicely alongside Blended, in that both represent a more mature depiction of love than is commonplace in broad comedies. It’s because Sandler’s movies, with some obvious exceptions, have seemed less interested in falling in love and more interested in making love work. If you look at all his movies together, and squint a little, you find a more refreshingly sophisticated perspective on romance than Hollywood likes to feed us. Bring on Murder Mystery 2!

23. Little Nicky (2000)

Ahead-of-its-time movie and not always in a good way.

By 2000, Adam Sandler was on a roll. Billy Madison begat Happy Gilmore. From there he stepped it up, made some more money with Wedding Singer. Then bam! The Waterboy, $185 million worldwide — boom! Big Daddy, $234 million worldwide — wow!

What did he use his newfound comedy superstardom to do? Make Little Nicky. It was a bomb the likes of which he wouldn’t see again for another 12 years. I didn’t see it in the theaters, but I remembered the day I rented it because I watched it and was so into it that I had my friends come over and watch it again — partly because it was funny to my teen brain, but more because it just wasn’t like anything I’d seen before. As the Ringer pointed out, the movie’s surreal, abrasive aesthetic was ahead of its time, coming out a year before the premiere of Adult Swim. Watching it now, it’s the film that would’ve most benefited from an R-rating, as well as a bit of recasting, since an empowered Sandler gave his three closest, not-famous buddies — Allen Covert, Peter Dante, and Jonathan Loughran — their biggest parts yet. It does get some points for being one of the pictures in which Sandler leans hardest into his character’s being annoying. Again, that’s a positive: Sandler is good at being annoying! Overall, the film leaves a positive impression, if only because it was Sandler’s biggest swing and a miss.

22. Spanglish (2004)

Sandler is tremendous in an important role in his evolution.

“I am sure, if this was this many decades ago, Billy Wilder would’ve hunted him down,” James L. Brooks told Charlie Rose on why he cast Adam Sandler to star in Spanglish. “If it was before that, Frank Capra would’ve hunted him down and got him. When you want a believable male character, who’s touching, who can act, who has comedy, and who is utterly truthful and sensitive, it’s just rare.” Busy with all facets of his own movies, and the fact that he’s a giant movie star, it’s not like Adam Sandler is auditioning a lot. Look at his non–Happy Madison career, and you see movies written for him, ones where the director can’t envision anyone else in the part. These movies offer a unique perspective into Sandler as an actor; you see how the director sees him. It’s like a painter knows they need a certain sort of yellow.

As Brooks mentions in the quote above, in this movie it was Sandler’s sensitivity he needed. There’s a scene where Sandler’s character is driving Paz Vega to her bus stop, and he’s trying not to scream after a moment of intense frustration with his wife (Téa Leoni). Vega’s character, as the narrator tells us, doesn’t know how to react, because he’s not like any man she knows and that his emotions are more like a “Mexican woman.” The movie sometimes flips and flops with its seriocomic tone, but Sandler seems locked in when others aren’t. In this supposedly sad, tough scene, when he finds out that his wife has been cheating, he does a nice job of finding small laughs that come off as deeply human:

Looking at Sandler’s career from a distance, Spanglish feels especially significant. He plays the sort of guy all his characters are trying to be one day. He has grown up. He has a successful career but also a close relationship to his family. He is overly sensitive but not anti-social. It is the goalpost the Adam Sandler of 1,000 faces was aiming to get closer to with each movie of the first era of his career. (It’s also notable that the kid-focused marital drama is closer to the movies he’s made in the second era of his career.) It isn’t the end of that phase, because Spanglish itself wasn’t in Happy Madison–verse, but it sure seemed to inform the end that would come two years later. You don’t have Click without Spanglish.

A dumb movie that knows it’s dumb.

When critics say they hate Adam Sandler movies, I assume it’s because of scenes like this:

So, let’s get into it. I get it in principle. Whatever bad taste is, it’s this. There are cheap laughs, sure, but there are intentional laughs. If you want to get technical, the comedy is in the contrast between Jill finally confronting her brother and the humbling sounds of her shitting. It’s a deeply human joke — as much as we pretend we are these high-minded beings with our jobs and conversations about books, we have a room in our house where we excrete waste like we’re some cattle. “We are gods with anuses,” wrote Ernest Becker in the Pulitzer Prize–winning Denial of Death. This contrast of our higher and lower selves can be applied to the scene on a metatextual level as well: It’s funny that a bunch of grown-ups went to work one day and orchestrated this scene. While we’re in the meta, it’s also funny because the audience is aware that both parts are played by Adam Sandler, and that means the two characters often cannot be in the same frame at the same time. In so much as we judge art by how successful the creator is able to articulate his or her vision, this scene is a tremendous success, completely in line with the history of Sandler’s comedy. Take this cut from his second album, What the Hell Happened to Me?:

Jack & Jill got especially a lot of hate because of how baldly stupid the premise appeared, but I think that’s partly what I like about it. It really is a very stupid movie. Just like there were times when Sandler has been like, Let’s make a Western or a kids movie, this felt like he said, “Let’s make a stupid movie.” And he did! The distinction between dumb things that the critic class calls “dumb” as a pejorative and things that are lauded as “dumb but in a good way” by comedy nerds has honestly been an obsession of mine since I began writing about comedy, and I’ve often asked the creators of the latter what the difference is. More often than not, they don’t see one. When I asked Andy Samberg about it earlier this year, when the Lonely Island was on an episode of my podcast Good One, he answered: “When I was a kid, and a teenager and I was obsessed with Adam Sandler and Jim Carrey stuff. I’d be like, ‘You have to watch this!’ and my friends or parents would be like, ‘I don’t know. It just seems stupid.’ I would always say, ‘Yeah, but they know it’s stupid. That’s the difference.’ They’re choosing to be stupid from a place of intelligence, and therefore that is making me happy. They’re saying, ‘We know what the world is, and in spite of that we’re going to spend our time on this as adults … If you’re the type of person who enjoys that — which we are and we hope that the people who like our stuff are — it’s a choice. It’s saying, like, ‘We want to make something dumb to make people laugh and smile and feel happy.’”

When I asked Scott Aukerman about this distinction in 2016, he had similar things to say: “I went to see Paul Blart: Mall Cop with my dad, and we sat there laughing and having a great time at the movies. You probably wouldn’t say it’s a sophisticated movie, but at the same time, how sophisticated are some of the old classic things that we love, like Three Stooges?” He added, “When you’re talking about smart comedy, what you’re usually talking about is playing upon audiences’ expectations of ‘Hey, we’ve seen this before a million times and we know generally how it’s gonna go and now here’s a smart twist on it.’” I contend most of Sandler’s comedies, and definitely all his best, have a handful of these smart twists (just like how smart-dumb comedies have a handful of dumb-dumb moments). Jack & Jill has a few. There’s Al Pacino’s incredible performance in the film, which has been celebrated on Twitter for the last year or so. And there’s the movie’s climax, in which Jack, trying to get on Pacino’s character’s good side, dresses up as Jill. Which means you are having scenes in which Adam is dressed up as a woman playing against Adam dressed up as a man who is dressed up as a woman. I don’t know that if you asked Adam he would quote Judith Butler or RuPaul, but in this moment he seemed to find a way of reviving lowbrow drag comedy’s ability to hold up the performance of gender for everyone to laugh at.

I’m aware that we are only halfway through and I’m spending this much time on Jack & Jill. This is the longest entry in the whole dang thing. Because Jack & Jill is the reason I made this list. You know, working on this thing, I found myself having a lot of conversations about Adam Sandler. Some people were curious, wanting know what late-era films they skipped that they actually should watch. Others we simply incredulous. More people than I expected just found Adam Sandler’s career confusing. This feeling is captured by the question I got a lot: After he made Punch-Drunk Love, how could he go on to making “shitty” comedies like Jack & Jill?

Here, in the entry for Jack & Jill, I’ll try to answer that question directly. My feeling is this question is based on a few incorrect assumptions. First, it assumes there is an objective “good” that critics and Sandler all agree upon, meaning that Sandler thinks his own movies are worse than the prestige movies he’s merely acted in. It also assumes that Sandler would prefer to act in a “good” movie than work on one of his own movies. As hard as it may seem to people, Adam Sandler likes his own movies. That’s why he made them. If he wanted to be in different movies, then he’d make those — he’s had enough cachet to do so, or at minimum enough money to self-finance, and there’s certainly enough prestige filmmakers who’ve talked about how much they love him. Though Sandler clearly enjoys acting and has fun experimenting with people he trusts, I would not call him an actor first. On his own movies he gets to act as well, but he can also express his artistic point of view. I think journalists have a problem of assuming the subjects they cover care about legacy as much as those covering them do (which makes sense — writers about culture are the ones who ultimately create the legacy). Some artists do! But more often than not, in my personal experience with mostly comedians, with people like Sandler, creators are motivated by the joy of expressing themselves (and, maybe, a pleasant work-life balance). To take it a step further, my guess is that this facet of Sandler’s career is what particularly makes him annoying to critics — his knowing what “good” movies are and still going back to make his “bad” movies directly confronts the agreed-upon ideas of taste, where highbrow exists in contrast to low.

Now imagine how often Adam himself has been asked this question, this question that has followed his career for nearly two decades, one he’s known to hate. Of course, with Uncut Gems gaining award buzz, the question again appears. Since it is such an incredibly sensitive subject, it took a close friend asking him for him to answer. I found the result really powerful. On a recent appearance on The Dan Patrick Show, Patrick started in on it by saying, “I think everything I’ve read on this was, ‘Why doesn’t Sandler do more of these?’” Which Sandler responded in the way he is in interviews: understated, humble, apprehensive. “How the hell is that supposed to happen? How many great scripts are happening every day?,” he asked rhetorically, before giving a bit of a nonanswer. “I mean, these guys are incredible. They gave me an opportunity and I like doing comedies too, so I can’t just throw away my whole life.” Patrick, surprisingly, tried to push back, saying, “I know your moneymaker is your comedy …” Sandler, who tends to be incredibly laid-back when being interviewed by his friends, interrupted him, clearly emotional: “It’s my love!” Patrick tries to de-escalate, pointing out that he’s just echoing what the critics are saying, to which Sandler responds, “I’m sort of talking to them.” Sandler doesn’t need critics for anything. He doesn’t care about his reviews. But what you see in this clip is a person, like many artists, dying to be understood. Patrick tries to push a little more and Sandler stops him, saying calmly, “I like what I do, man, and I like it a lot.”

It reminds me of when Judd Apatow was doing press around Funny People and he would explain that when they were starting out, “Adam had so much energy to be funny that he would be very funny with strangers on the street.” I remember Apatow saying somewhere that Sandler would put all the comedic force he had to make one person laugh that he’d go on to apply to the world. And that’s it. Sandler is driven deeply by the desire to make as many people laugh as he can — he doesn’t care about how old they are, where they live, if they are the movie critics for a major newspaper. Jack & Jill made nearly $150 million worldwide. Again, it’s not about the money; it’s about the people, and specifically people laughing. More people saw and laughed at Jack & Jill than Punch-Drunk Love. Jack & Jill was a success. I’m aware that it’s literally way lower on this list than PDL, but again I’m not arguing it’s the best movie he’s made or that it best articulates his vision — just that it’s better by those metrics than a lot of his movies, especially most of the dramas he’s made since the movie that was supposed to teach him to become a real actor. It’s his love.

20-11 S O G O O D

A rare creative power struggle for Sandler leads to the surprisingly delightful, tremendously successful trilogy.

Photo: Sony Pictures Releasing

In his dramatic work, Sandler consistently pushes himself to work with visionaries; in his comedies, he instead works with friends who function more as collaborators. The exception is the Hotel Transylvania series, which quietly has grown into a box-office behemoth at a time when live-action Sandler has faltered. The history of Hotel Translyvania’s development is a particularly long and involved one (if you’re curious, I suggest listening to the Blank Check episode about the series), but briefly: After five directors were attached and unattached, it eventually landed in the hands of Genndy Tartakovsky, an animator’s animator who already had Dexter’s Laboratory, Samurai Jack, and Star Wars: Clone Wars under his belt. At the time, Sandler was still the comedy king of Sony, the studio behind the project, so it threw him in. The result has been, as Blank Check put it perfectly, an “arm wrestle for auteurship.” Yes, seriously.

Simply, Tartakovsky wanted to make a movie showcasing his impressionistic visual style and Sandler wanted to make one with a bunch of dumb bits aimed at an audience too young to care about what a critic would think is good. In spite of this clash, or maybe because of it, all of these movies are, frankly, great! Whatever power struggle may have happened behind the scenes, the product was not infected with any bad vibes. Ultimately, the struggle just means your preference will come down to which of the movies you’re more likely to be a fan of.

The Ur-Hotel Translyvania, despite being co-written by Robert Smigel (though clearly all these movies have been written and rewritten by a number of people), feels most like a Tartakovsky movie. The pacing is the more deliberate and dynamic than the other two, and there are just way fewer bits. The plot feels Sandlerian, with the story playing out somewhat like The Waterboy: A parent selfishly cloisters a child so as to not lose the child. And obviously the cast — Kevin James as Frankenstein(’s monster), Steve Buscemi as a werewolf, David Spade as an invisible man — makes it unmistakably a Sandler movie. However, much of the comedy comes from the animation rather than scripted jokes and vocal performances.

The third one, which was the highest grossing of the series, makes the least sense — why would they need to go on a vacation from being a hotel? — and is by far the most all over the place. Yet, it somehow works. It just has everything. It’s a compromise, the way a husband who wants sushi and a wife who wants Italian end up flying to Las Vegas to spend an entire day at Caesars’ “Buffet of Buffets” is a compromise. It’s madcap and weird and all around a freaking blast.

Still, this is a list about the Adam Sandler–ness of Adam Sandler movies, which is why Hotel Transylvania 2 comes out on top. Sandler is credited for co-writing this installment with Smigel, and it plays like the old SNL friends deciding to turn the film into an animated, monster-themed sketch show. It’s full of really strong, really funny bits and silly non sequiturs. Add in Sandler’s voice work, which is great throughout, and the result is number of really laugh-out-loud moments. Dracula’s impression of his daughter and son-in-law talking about how their son hasn’t gotten his fangs yet is one of my favorite scenes from Sandler’s entire career.

Considering this is essentially the only place you can see Adam Sandler’s work on a big screen these days, you could do a lot worse.

17. Anger Management (2003)

A perfect setup for one of the funniest movies in the canon.

Let me get the bad out of the way: The ending of this movie doesn’t make sense and is very annoying, and not just because it prominently features Rudy Giuliani a.k.a. Adam Sandler’s most problematic fave. But before you get to that point, you get a great extension of Sandler’s comedic tools, as the film’s premise is an ingenious foil for Sandler’s style. In it, he plays a seemingly mild-mannered, repressed man forced to go through a one-on-one anger-management program, with Jack Nicholson as the therapist who finds every way possible to push his buttons and let his anger out. It’s a sort of reverse Happy Gilmore — instead of finding comedy in a loose cannon trying to be controlled, here is a suppressed cannon constantly being triggered to fire. And Nicholson, with his perfect late-career IDGAF attitude and body, is the perfect bear poker. Similarly, Anger Management effectively refines the lesson Sandler’s character learns in Gilmore: You have to be able to control your anger, but not to the point of complete passivity. It also features this scene, one of the most fun things Sandler has ever filmed:

Will Adam Sandler win an Oscar one day?

Will Adam Sandler win an Oscar one day? Watching The Meyerowitz Stories, it sure seems possible. (In my estimation, one of the biggest things standing in his way is his disinterest in doing press and dressing up, yet you saw him wearing a suit more on this press tour and doing some things like the Variety Actors on Actors interview.) Thirty years into his career, it’s clear that with the right project and right director, Sandler definitely has the talent for an Academy Award. That’s not something I’d say about any other of the male comedy superstars of his generation. Others might be more consistent actors, but Sandler has another level, where in the right role he can find something deeper. He just needs his Lost in Translation, something that can play to all his comedic strengths while also giving him room to look sad and alone. You don’t want Sandler to transform as much as play with the tools he has and the audience’s expectations of him. The result will be a lot like his The Meyerowitz Stories role.

The seeds of this project were planted by Sandler, who wrote Noah Baumbach a letter asking the writer-director to consider him for something. For Baumbach, it was a no-brainer. “I don’t feel any relationship to that debate [of whether he’s a good actor],” Baumbach told Newsweek. “I’ve always really liked him. It was clear to me how good he is. When you sit down with him and meet the guy, there’s such a depth of sensitivity.” Baumbach, clearly a fan, created his own version of an Adam Sandler man-child, one who knows more about art and whose relationship with his father has frozen his emotional development. Also, as a student of Sandler, Baumbach knew nothing brings up his pathos like making him a parent. I’m sure some found the duet with Grace Van Patten maudlin and forced, but it is an Adam Sandler scene through and through and easily one of his most lovely onscreen moments:

At this point in his career, this is arguably his best character performance, with Sandler finally figuring out (in large part thanks to a good script) how to play a regular New York guy. The result wasn’t an Oscar, or a nomination, or even a real campaign for one (it didn’t help that it was on Netflix and that the part wasn’t clearly supporting or lead), but you can see the potential for one in the headlines for reviews of the film: “Adam Sandler Is a Revelation,” “Adam Sandler Shines,” “Seriously, Adam Sandler Triumphs in The Meyerowitz Stories (New and Selected).” It’s the part that erased the question of whether his other serious turns were flukes. Adam Sandler is a good actor.

Just friends hanging out; exactly as imagined.

I had a hard time putting my finger on exactly what I loved about Grown Ups 2 until I read this burn in the Variety review: “[Among the] least movie-like movies released by a major studio in the last decade.” It’s probably a similar perspective that landed it at No. 5,268 on Vulture’s ranking of every movie of the 2010s. But it’s unmovieness is what I think makes it work so well for what Sandler was trying to do. Grown Ups failed by trying to orchestrate a plot to justify why a bunch of people would hang out, whereas Grown Ups 2 is just a celebration of hanging out. At times it feels like a mumblecore sketch show — just a bunch of two-person scenes of funny people riffing and vaguely playing characters. This will give you an example:

Adam Sandler movies are often escapist. He’ll drive nice cars, hook up with beautiful women, and so on, but the real wish fulfillment is metatextual. He creates movies where you wish you were Sandler getting to make the movie in the first place. He gets to shoot in exotic locations, with his best friends in the world, and wear the most comfortable clothes possible to work. This movie ends with a big party, filled with former SNL cast members (the film features 15 in total, just short of the Coneheads record), dressed in ’80s costumes, and it looks like a blast. There isn’t much cinematic value to it, but it is fun to imagine being invited to it. In that regard, the film is a tremendous success.

14. Eight Crazy Nights (2002)

Animation and singing free Sandler to be grosser and more self-loathing than ever before.

Considering how big a role music played in Sandler breaking through at SNL and in his stand-up, it’s a shame his movies aren’t more musical. The exception, of course, is his take on a holiday movie, Eight Crazy Nights, which features seven original songs co-written by Sandler. One impressive bit is “Technical Foul,” which features a three-part harmony all song by Sandler:

Animation obviously allowed him to push some disgusting-ness boundaries in the film, but I am more interested in how he used it to further flesh out his man-child persona. Because it’s traditionally a medium for kids, animation allows for a certain amount of directness. Throw in musical numbers, which are literally shouting your feelings, and you get Sandler being more upfront about the self-loathing that lies underneath all his characters. It’s the pit they climb out of over the course of every movie. Usually, it’s subtext, conveyed only by Sandler’s big, sad, Pixar-eyes, but it’s essential to any “Sandler isn’t so bad” theories (like this one!), as it gives his movies depth. Here, he sings right at the start, “I hate love, I hate you, I hate me.”

The open-hearted simplicity of animation and musicals — not to mention animated musicals that are also holiday movies — is a nice fit for Sandler schmaltz. It’s not just the lowbrow poop jokes that rub his critics the wrong way; it’s also his overt sentimentality. It’s a point I’d quibble with, but either way, that sentimentality feels appropriate in this context. Rewatching the films in order, it was the first to make me cry.

Sandler finds some of his best comedy in specificity.

Adam Sandler told a story on Norm Macdonald Live about working with Rodney Dangerfield, in which he retells the comic legend’s response to the “Hanukkah Song”: “Kid, don’t tell ’em you’re a Jew!” Sandler represents an interesting point in Jewish representation in film and the assimilation of Jews into mainstream American society. He offered a version of Jewishness that was not nebbish or urbane or intellectual yet still positioned as an outsider, bullied by country-club types and O’Doyles. For the most part, he blended in, like the decades of celebrity Jews he sings about in “Chanukah Song.” So, there is something noteworthy about Sandler being so proudly Jewish, and implicitly Jewish in many of his movies (names that can’t go either way; nose jokes), and yet still be coded as a “regular guy” in his movies.

You Don’t Mess With the Zohan is radical by contrast. Of course a story written by Sandler, Robert Smiegal, and Judd Apatow about a former Israeli soldier turned hairstylist will be Jewish, but what makes it stand out among Sandler’s work is how specifically Jewish it is. In that The Waterboy succeeds by the ridiculousness of its stereotype, and Blended and Ridiculous 6 falters in the shallowness of theirs, Zohan is easily one of Sandler’s funniest movies because of how specific and lived in its stereotyping feels. Beyond all the creatively silly hummus jokes, the character at the core of the thing will ring true to anyone who’s been on Birthright and met a soldier equally adept at punching and fist pumping. Subsequently, Sandler has a freaking blast, being so secure in his masculinity, dancing into and out of every scene, shaking his little butt cheeks, and telling some of the best jokes of his film career. Sandler admittedly tries to make comedies large audiences can understand, so it’s just fun seeing him not water down his energy. And yet Sandler was so on fire at the time it was a domestic and international hit, grossing nearly $200 million worldwide.

A disclaimer: The film was originally written in 2000 and delayed after 9/11. Though far from dogmatic, the overall politics don’t hold up great. But again, Sandler’s comedy isn’t malicious as much as misguided in its representation. So, yeah, there are Muslim terrorists, but they are also shown as people with lives and interests and not subhuman villains, which, umm, could’ve been worse.

12. Uncut Gems (2019)

In which he uses all the tools in his acting tool belt to condemn the idea of Adam Sandler.

Photo: Courtesy of A24/©A24

In essentially all of Sandler’s flirtations with drama, the opportunity comes about because a cool and/or fancy director who loves him wrote a part with him in mind. The given director then has to convince Adam why he’s right for the part, with the Sandman only accepting the things he thinks he can do. We don’t know a lot about what he declined (passing on the role in Michael Mann’s Collateral that earned Jamie Foxx an Oscar nod is maybe one of the better-known examples), but there are similarities to what he’s decided to do. Often the characters are mild-mannered, with Sandler’s sweetness and heavy-heartedness amplified, and generally they are, as with Sandler’s own comedies, telling stories about someone who wants to be better. Uncut Gems is different because while it’s clear the Safdie brothers, who grew up on Sandler, care about him and his acting a great deal, they decided to use his power for evil instead of good. Well, maybe not evil — but at least cynical where he would normally be idealistic.

Not to get all Nanette on you, in so much as any comedian has a variety of tools to build and relieve tension, but the Safdies used all of Sandler’s talents only in service of the former. Most important, it is his first drama to intentionally lean into Sandler’s taste for playing annoying people. In the film, Idina Menzel, who plays his wife, literally tells Sandler’s Howard Ratner, a jewelry dealer and gambling addict, “I think you are the most annoying person on the planet.” Almost as if to bait the critics who find his annoying characters annoying, the Safdies reward Howard with a Job-like existence of constant disappointment, failure, and self-sabotage. In turn, the Safdies use Sandler’s sweetness and lovability as a sort of trap to lull the audience into a false sense of security, to trick the audience into hoping for a hopeless character.

And, fuck, Sandler is so good at all of it. Besides being his best character performance, Sandler has never seemed more natural in a role. In his Variety Actor on Actors conversation with Brad Pitt this award season, Sandler talked about how this is the most comfortable he felt acting in a film like this. “I’m feeling like this guy,” he told Pitt. “I really did my back story. I worked hard at this character, knowing the way he thinks and where he goes. I knew the guy.” Maybe for the first time in his career, you really lose Sandler in this role, to the point where you just see Howard.

When Variety asked why Sandler was right for the part, Josh Safdie explained, “Because he’s a maniac, [for whom] there’s never enough. And he can always see that there’s this kind of Elysian field that he can get to and you see it in all his of work.” Though similar to my perspective of Sandler the dreamer, the self-actualizer, it reads a bit more cynical. Through the prism of the Safdie brothers, the desire to be better, which I offer is the fundamental Sandlerian motivation, becomes the desire to want better.

Which brings us again to what Sandler represents to American Jewry, as the Safdies clearly knew the Sandman could serve as a sort of idol of Jewish Assimilation whom they could ceremonially question and destroy the myth of. What is the price of assimilation, both in terms of the literal suffering of people and the figurative suffering of the soul of Jewish people at large? (Upon watching, the title seems to be a clear wink to the loss of Jewish identity in the hope as passing as regular, wealthy white Americans.) Uncut Gems is an incredibly rich, thematically ambitious movie that is able to be told deftly, at a breakneck pace, because of Adam Sandler and the magnitude of both his performance and what he represents.

A very sweet tribute to getting to make entertainment with your friends.

There is a lovely section in the recent New York Times Magazine profile of Sandler, in which writer Jamie Lauren Keiles just lists all the secondary quotes they received:

“‘I would lead with “Loyalty is his motto” ’ (Aniston). ‘Sandler is a very loyal guy to his friends’ (Kevin Nealon). ‘I have enormous, enormous affection for him’ (the producer Scott Rudin). ‘Such a menschy, sweet person’ (Judd Apatow). ‘Really down to earth’ (Nick Swardson). ‘He’s a great guy’ (Spade). ‘I love, love, love him!’ (Paul Thomas Anderson). ‘He really cares about people’ (Kevin James). ‘Very generous with his own praise and support’ (Robert Smigel). ‘He’s very loyal’ (Herlihy). ‘Incredibly loyal and nice’ (Conan O’Brien). ‘His level of loyalty is unparalleled’ (Netflix’s chief content officer, Ted Sarandos). ‘If he goes somewhere, I’ll go with him, no matter where’ (Schneider). ‘If you want to text or email for any little thing that comes up, please feel free to bother me. Anything for Adam’ (Barrymore).”

The more cynical, as the profile notes, disregard this trait as laziness or “grift to keep Sandler’s mediocre friends in the money,” which he shoots down by saying it’s just more fun. But I’d argue, as will always be with Sandler, he is understating it. Having fun with friends — his loyalty to them — is one of the main creative drives of his career. As I was told by someone who worked with him, it’s a motivation only intensified by the passing of close friends like Chris Farley and Gary Shandling.

Sandy Wexler, the movie he made after Shandling passed, is the next logical step from Grown Ups 2, placing this part of Sandler’s comedy front and center. As I wrote when the movie first premiered on Netflix: “Sandy Wexler is not just another movie where Adam Sandler gets to have fun with his creative friends; it’s a movie about getting to have fun with creative friends.” In it, Sandler plays a manager of misfit toys, loosely based on his own real-life manager, Sandy Wernick. So the plot is just him going from one of his friends to the next and laughing at the ridiculous characters they’re doing. (Terry Crews is particularly funny as a professional wrestler who rocks his opponents to sleep.) Add in the interstitials featuring more of Sandler’s friends — Janeane Garafalo, Judd Apatow, Henry Winkler, Lorne Michaels — politely roasting Sandy. The result is the sweetest movie of Sandler’s career. Of his later works, this is the movie that best captures what he’s trying to do with his work. If he’s making movies to make people laugh and have fun with his friends, Sandy Wexler succeeds at both.

10-1 T H E B E S t

10. 50 First Dates (2004)

A career-spanning partnership that reflects maturing ideas of love.

Three days before 50 First Dates premiered in thousands of theaters across the U.S., a spiritual second cousin premiered at Berlin International Film Festival: Before Sunset. The plots are different, but the way both deal with the relationship between love and time both textually and metatextually is similar. Of course, the Before series tells the story of the same characters over the course of three films (1995’s Before Sunrise, 2004’s Before Sunset, and 2013’s Before Midnight), but part of what makes them so affecting is seeing how the time between films has changed the actors and how the actors relate to the characters. Because Adam Sandler and Drew Barrymore play variations of their archetypal characters in their three movies together (1998’s Wedding Singer, 2004’s 50 First Dates, 2014’s Blended), a comparable thing happens watching them grow both onscreen and off.

With the context of seeing Sandler and Barrymore together again, but now a bit older, the plot of 50 First Dates itself plays with time. Where Before Sunset literally takes place over one day, 50 First Dates essentially does as well, with Barrymore’s character resetting every 24 hours. Sandler has to then convince Barrymore to fall in love with him every day and it is all really cute and charming and they are so lovely together. Barrymore is especially winning playing a character who falls in love 50 times in the same movie.

Both the Before series and the Sandler-Barrymore series look at love and marriage through the lens of a generation who grew up in a time of increased divorce rates. Sandler, possibly because his parents remained together, approaches this from a much more traditionalist point of view. Though Barrymore originally found the script and sent it to Sandler, saying it should be their next movie together, Sandler rewrote the drama into, well, an Adam Sandler movie. This means now a walrus was going to aggressively vomit all over Sandler’s co-worker, but also that Sandler could make it more personal. Having gotten married a year before 50 First Dates came out, it’s interesting to see how Sandler’s understanding of love and relationships evolved since his first collaboration with Barrymore. Love is no longer a thing you work toward but something you work at. It’s not a noun, it’s a verb. Sure, it sounds cheesy, but Adam Sandler is cheesy.

9. Happy Gilmore (1996)

Sandler’s angry clown on full display.

The early stages of a comedian’s career is about finding your clown — the core of what is funny about you — and then acclimating audiences to it. It’s more than finding a persona, because for comedic actors, what is funny about them is constant even if they are playing different characters. Through SNL (which is like clown-finding bootcamp) and his albums, Sandler had a good sense of who he was by the time he made Billy Madison. But it wasn’t until Happy Gilmore that he showed a wide audience the full force of the comedic trait that would go one to define him: his anger. In basically every movie that follows, Sandler would expand upon his comedic rage, but in Gilmore it is front and center. And while Sandler is clearly not totally comfortable on-camera yet, he is at least a present and compelling to watch.

There is, however, more to it. The key to Sandler’s comedic anger, and arguably the key to the acting career that came out of it, is sensitivity. Every fancy director who’s worked with Sandler will point to this as why the decided to work with him. It’s not a sensitivity in conflict with his rage, but at the core of it. Here’s what it looks like:

This moment, though not the most iconic scene in a particularly quotable movie, is a bit of a Rosetta stone for understanding the characters Sandler plays. In many of his movies, it’s usually established that one or, in the case of Gilmore, both his parents died or are absent. It’s how the movie tries to explain the arrested development he plays so well. But it also deepens him. Sandler’s characters act out owing to a tremendous need to be loved, appreciated, understood. Happy grows up relatively little for a Sandler character, with him not learning to not be angry anymore but rather to control it long enough to play golf. It’s a lesson Sandler similarly had to learn in his acting: getting angry more sparingly, or even not exploding at all — just playing it so that the audience knows it’s underneath. Sandler became a better actor right after Happy Gilmore. He just needed a movie where he could get it all out.

And that’s why it’s here on the list. Considering so many people I talked to while working on this assumed Happy Gilmore would be top two, I’m sure after seeing (and hopefully reading) what was No. 1, a lot of you control-F searched “Happy G.” It’s really great, but I think because of childhood nostalgia it stands as maybe his most overrated movie. Yet this is undoubtedly an important movie in Sandler’s growth as a comedian, as he still is clearly figuring things out (Billy Madison has a learning energy, but it also was more of a mission statement). You look at the movies that directly follow Gilmore and you see a much more ambitious, skilled, dynamic moviemaker, able to create work that encompasses more of what he’s trying to do.

Working with an old friend + stand-up = one of the most interesting performances in Sandler’s career.

Photo: Universal Pictures

Adam Sandler had to turn down a role in Inglourious Basterds, playing the Bear Jew, because he was already committed to shooting Funny People. Sandler, of course, would’ve been fantastic playing the part that eventually went to Eli Roth, and Basterds likely would’ve been the best movie Sandler was ever able to be a part of, but it was worth it. What Sandler got instead was the chance to work with a director who really knows him. To his credit, if you read interviews with the more auteur-leaning directors he once worked with, you get a sense that Sandler works hard, listens to direction, and trusts his collaborators fully. The difference is Sandler and Apatow had known each other for most of each other’s lives, even living together when they were up-and-coming stand-ups. Apatow just knew what Sandler could do, and the result is one of the richest performances of his career.

What performance?, critics might respond, suggesting the Sandman was just playing himself. The irony being that that very feeling is proof of how good Sandler is in this movie. “This guy that I play is leading a different life than I live,” Sandler said about his George Simmons around the film’s release. Yes, George is a giant comedic movie star who makes, let’s say, populist fare, but Sandler unlike George is not alone, as he famously surrounds himself with his family and friends. Similarly, some people saw Funny People as a rare bit of self-awareness from Sandler, showing that he also knows his movies suck. Yes, there was a degree of self-awareness here, but of a different sort. Considering the movies he proudly went on to make afterward, I saw the shitty movies they have George star in as a comment not on Sandler’s work but on the popular perception of Sandler’s work. If anything, based on how Apatow has talked about realizing the movie was much more about him than Sandler, George’s shitty movies are mostly a manifestation of how Apatow sometimes feels about his own work.

Anyway, the point is they are different. But what is exceptional here is how Sandler and Apatow pull from their real lives to give the performance verisimilitude. Every time George Simmons talks about Seth Rogen’s character’s penis, it feels like you’re getting a clear picture of what it’s like being friends with this guy from someone who is. What’s so great about watching Sandler in Funny People is how he seamlessly blends all these things together to create a fully formed human being for the audience to observe.

To achieve this, the smartest decision Apatow made was having him do stand-up — like really do it in front of real audiences, not just shoot some cutaways and add the laughs in post. In the same way that in Punch-Drunk Love, Paul Thomas Anderson, as a great filmmaker, is able to convey to the audience what it was like for him to fall in love with Adam Sandler as an actor, watching Funny People you feel how Apatow felt when he would see Adam Sandler do stand-up when they were coming up together. As is now clear to everyone who watched the universally lauded 100% Fresh, something special happens when Sandler is alone onstage. He seems more vulnerable, more present, more connected. Not only was Sandler not really doing stand-up before shooting Funny People, he admitted being nervous about sharing that side of himself with his audience. “I would tell Judd after every set I would do, this was stuff I haven’t done in a long time. I haven’t talked that filthy in front of people,” he said in an interview. For followers of his work, it was just so exciting to get to see more of him, to get to fill out the picture of who he is and the character he has been playing.

In so much as Sandler’s career is about telling a single story about growing up and being grown, Funny People goes the other way up the mountain but gets to the same place. Apatow was less interested in linear growth and a fully happy ending, but Funny People is essentially his version of Click, a movie by a workaholic about a workaholic learning that family is the most important thing (even if it’s your chosen family). Sandler’s characters end movies better than they started, even if it’s only a little bit.

7. The Week Of (2018)

Sandler masters Dad-Adam in one of his most ambitious pictures.

If there is one bit of Adam Sandler conventional wisdom I can most confidently debunk, it’s that his Netflix movies represent the low point of his career. There seems to be a perception that they are the tossed-off victory lap of a washed up, finally failed movie star. In reality, they’ve clearly been a creative reinvigoration just when he needed it. I’m not sure if it’s the budgets or the creative freedom, but the movies have all been among his most ambitious, and his performances his most engaged.

Take the most interesting of his offerings thus far: The Week Of, a movie in which Adam Sandler plays a father whose daughter is marrying Chris Rock’s son. I watched it and thought it felt like Sandler’s version of a Robert Altman movie, as the thing has like 44 billion characters, each impressively with their own specific comedic game. However, apparently another legendary director was the touchstone. Director Robert Smigel, who co-wrote the movie with Sandler, is quite cute talking to the L.A. Times about how Sandler pitched him on the idea, so I’ll let him tell it: “It’s going to sound funny, because you just imagine Adam saying it in his goofiest voice, but he made it clear when he pitched me the initial idea that he wanted it to feel much more vérité. That word alone out of Adam’s mouth — vérité. He wanted it to feel like a naturalistic ensemble movie, and we even talked about directors like [John] Cassavetes.”

The Week Of is the purest essence of the new older Adam Sandler, and the result is the most understated, naturalistic film in the Happy Madison–verse. The whole thing is shot handheld, for God’s sake! And at the center of it is Sandler, a father of the bride trying his best to keep his daughter’s wedding together despite a lack of funds, wit, or charm. Comedically, it’s a nice reminder that Sandler is much funnier when playing low status because it’s just more believable. And in terms of pathos, Sandler brings more than he has in any movie of his own movies since Click.

In many ways, The Week Of is a fully formed vision of late-career Sandler. His first 15 years were about his version of the man-child (with some exceptions), and his last 15 (with some exceptions) were about Sandler’s version of Dad. Sandler has slowly but ever increasingly moved from playing to man-children to dads. Not dad-children; just dads. Dads that are equal parts sweet and heavyhearted. Dads just trying to do their best and, in turn, failing at it for laughs for the first two acts. It came together slowly — Big Daddy begat Spanglish begat Click — and dramatically peaked with The Meyerowitz Stories. And all of this went into The Week Of.

Similarly, how his movies are produced reflect the themes of the movies themselves. From looking at his work, from the point he married Jacqueline Titone in 2003 and especially after they started having kids, the only thing Sandler seemed more driven and inspired by than friends is family. His kids occupied all of his thoughts, as he said around the release of Grown Ups: “The idea of my kids being spoiled, I go to sleep thinking about it and I wake up thinking about it.” He would shoot his films primarily during his kid’s summer vacations, so they could be on set and eventually on-camera (eldest daughter Sadie has appeared in 17 of her father’s films, and Sunny has been in 15; both have more movies appearances than years they’ve been alive). Also, as the Times profile noted, he created a schedule to take and pick up his children from school. Onscreen, his characters have had to figure out how to reconcile the men that they are with their duties as a husband and father. Providing became a prominent theme — not just about the anxiety to make enough money to give your kids a good life, but also the anxiety of giving them too much.

Because of how prolific Adam is and how much control he’s had, you can so clearly see what was on his mind every year of the last quarter-century; what happens in his personal life mirrors the themes of his films. It’s unclear if this current phase will continue (Uncut Gems, a weirdly similar though completely opposite movie about a different sort of Long Island Jewish dad, trying his best by lying a lot, fits nicely), but it is clear The Week Of will be seen as a peak.

6. The Waterboy (1998)

Adam Sandler at his funniest.

Photo: Buena Vista Pictures

After, earlier that year, Wedding Singer proved that Sandler could be a leading man, The Waterboy proved he was a movie star. Billy Madison grossed $25.5 million domestically. Happy Gilmore followed that up by grossing $38.8 million. After that, Wedding Singer grossed $80.2 million. But then, The Waterboy grossed … $161.5 million! Which is a lot! When you account for ticket inflation, it is still Sandler’s biggest movie. For the most part, this was likely just the result of a fan base slowly building, especially with Happy and Madison getting heavy cable rotation, but the movie also just had the most amount of Adam Sandler comedy. In most of his movies, Sandler balances his main comedic tools, but in Waterboy, the simmering aggression, the man-child, the annoyingness, the ridiculous/offensive portrayal of a culture — they’re all maxed out. And, sure, Bobby Boucher is irritating, but at the same time he’s oddly grounded and lived-in for a Sandler character, likely coming from the fact that he’s continuation of the Excited Southerner he played on What the Hell Happened to Me? As well as Canteen Boy on SNL. Also, although Bobby is a heightened character, his arc, which is a bit of a fusion between Billy Madison and Happy Gilmore, feels like the platonic ideal of a Sandlererian how-to-be-a-grown-up narrative. Ultimately, where his previous films felt like Sandler figuring out how to do his thing, here he was at full strength, with a fully realized clown. He’ll have more dynamic performances to come, but he was never funnier.

Adam’s sensitive side breaks through.

“Big Daddy had sensitive Sandler,” Paul Thomas Anderson told Bill Simmons on his press tour for Phantom Thread, explaining why he wanted to work with Sandler in Punch-Drunk Love. “There’s a scene in it where he’s screaming at his father over the telephone that I used to rewind over and over. That’s when I really thought, I have to find this person. I have to work with this person.” The video below is not the best quality (put your sound up), but still you can see so much of what became Sandler’s PDL character:

What you see is a bit of a breakthrough in terms of his man-child character, resulting in something more psychologically damaged, something more needy. Many Sandler movies follow an arc not like an episode of Queer Eye: A young man is stuck and needs the help of an outside force to understand what it means to be a man.

Why Big Daddy works so well is because that outside force is an actual child. Here’s the thing about the man-child: Over the last 30 years, at least, usually the term referred a 30-plus-year-old man who acts like a teenager or college kid (literalized by Old School). But Sandler often plays an adult who lives like a kid between the ages of 9 and 11. Big Daddy, the first movie where he has a kid, shows how fun Sandler than can be relating to someone who is the age he acts. A kid brings out his sweetness and sensitivity, so that when he eventually grows up, it’s that more satisfying. In that way, Big Daddy predicted the parts Sandler would go on to play later in his career. Honestly, if it weren’t for some frustrating and clunky parts of the film’s climax, it could’ve made a case for topping the list.

4. Billy Madison (1995)

Sandler tries to show his generation how to grow up.

Adam Sandler famously didn’t really do interviews for decades. He did late night, but the only time he talks to the press tends to be at junkets, where the interviewer doesn’t have much time to get at much. The story goes he was so taken aback by the negative reviews for Billy Madison when it came out that he decided he and critics and, in turn, journalists simply don’t get each other. That assumption was then confirmed to him by the reviews for Happy Gilmore and almost all of his subsequent movies. This has meant, until very recently, that the only place you’ll see a long interview with Sandler is on the radio shows and podcasts of friends — Dan Patrick, Norm Macdonald, Conan O’Brien. And even in those, Sandler leans toward soft-spoken and humble or, at most, just one of the guys.

As a result, it’s become easy for people to think of Sandler as unambitious and lazy since they’ve rarely been told by the man himself that he actually has a vision. In preparing this list, I’ve found one brief exception where he admits to trying to do something specific and believing, regardless of what the critics thought, that he achieved it. It was on The Dan Patrick Show, in 2017, where he was talking about how he never reads reviews because “pretty quickly, they went against him.” “Billy Madison they slammed, and I didn’t expect it,” he tells Patrick. “I was like, ‘Oh, these guys are going to see I’m trying to do something — I don’t know — connecting to my generation, blah blah blah.’” They didn’t. The thing is, that’s most of Sandler’s movies.

Dr. Aaron Taylor, a professor of media studies, made a case in the academic essay collection Millennial Masculinity: Men in Contemporary American Cinema for Sandler as an embodiment of the masculinity crisis, in which men of a generation were struggling to find their role in society, as it was no longer as simple as “sole breadwinner.” Without direction, Sandler’s men freeze, incapable of working, maintaining a healthy relationship, and being a functioning member of society. (This is often in contrast to the female characters, who tend to be put together professionally and emotionally.) But unlike, say his old friend Ben Stiller’s attempt at connecting to their generation with Reality Bites, which came out a year earlier, Sandler doesn’t offer alternative solutions to this crisis. No, Billy Madison and, in turn, the rest of his movies affirm certain conventional orthodoxies: go to school, have a career, have a family. Executed with a Sandlerian simplicity, his movies often play like kids movies for adolescent (or stuck-in-adolescence) men, providing them an easily digestible lesson on how to live.

Billy Madison was the first of these movies and its purest distillation. His exuberance was infectious, and still is all these years later. It’s a goofy performance, with him doing the kinds of silly voices associated with the audio sketches from his albums. You know the lines: “Conditioner is better.” “Stop looking at me, swan.” “Chlorophyll? More like BOREophyll.” But the moment that really struck me watching it again is when his dad tells him that not only is he not going to put Billy in charge of the family company but actually he has been paying for him to pass every grade since he was little. Left alone on the mansion’s staircase, Billy’s reaction to this is to dance to music that, we have to assume, is playing in his head:

Sure, it captures how immature and un-self-aware the character is at this point, but also it captures just how much fun Sandler is having. Depending on your take on the actor, that is Sandler at his best or worst, but it’s undoubtedly him at his most Sandler.

An auteur’s beautiful tribute to Adam Sandler movies.

Around the release of PDL, Paul Thomas Anderson and Adam Sandler went on Charlie Rose. Rose asked PTA what inspired the film. After acknowledging the real person who figured out an airline-miles scheme like the one depicted in the movie, he said the film’s “main impetus is wanting to write something for Adam.” And you can tell. Punch-Drunk Love is a love letter from someone with a deep Sandler fandom. (Side note: In that same Rose interview, Anderson mentioned that he and Jonathan Demme are in competition for who is a bigger Adam Sandler fan.) While Sandler’s other dalliances with auteurs might involve them playing upon what we know and expect from Sandler and his movies, Punch-Drunk Love is special because it’s an attempt to actually make an Adam Sandler movie, allowing us to see them through Anderson’s eyes. The elements are there: Man-child, failing to thrive; a more emotionally mature (albeit underwritten) love interest who helps give him something to shoot for; a scheme that helps push him toward maturity; daddy issues; a bully. Hell, this film might’ve even introduced Sandler to the idea of building a vacation to Hawaii into the shooting schedule.

And there’s Adam Sandler, who is exquisite in the role that he told Rose reminded him of himself, his brother, and his “friend Judd” (hehe). Anderson told Rose he was taken, though not surprised, by just how hard Sandler worked, and it’s evident in the performance. This is not to say you can see Sandler acting. Hardly. Anderson asked Sandler to take what he was already doing and just push it — be more raw, be more vulnerable. His sweetness became more shy. His temper, while still funny, became a bit more scary. His self-loathing became full-on clinical depression. It’s hard for a film and actor to capture an introvert, since a movie sort of needs its main character to interact with the world, but Sandler is incredible at playing a person who doesn’t want to be looked at but you can’t keep your eyes off of. In total, you get to see Sandler figure out how to become a much more internal actor. Watch how all the traits we associate with a Sandler character play on his face in this scene, only to explode at the end:

I considered not putting Punch-Drunk Love so high because of how it so quickly became weaponized against Sandler. For a certain sort of critic and critically minded viewer, with every new Sandler movie, Punch-Drunk Love would be pointed to as an exception. Either Sandler could make great work but cynically chooses not to in order to make more money, or Sandler is a talentless oaf who somehow was able to achieve something actually good with the help of a visionary director. I, especially after watching his films in order, see it a bit differently. This list is partly about how Sandler chose a career in which — unlike, say, Jim Carrey or Will Ferrell — he almost exclusively plays variations of the same core person. It’s allowed him to continue to both sharpen and add nuance to the picture of who this archetype is. Because it happens in real time, for some fans, what we learn lingers with each project that follows. When you watch the Sandler movies that come afterward, regardless of their quality, they are all made a bit better knowing that, the Punch-Drunk Love character lives inside there as well. These other films don’t get into the depth of his loneliness and depression, but it’s there.

Have you watched The OA? I’m serious. Esssssssssssentially, characters travel in between dimensions, landing in the body of whoever they are in that existence; sometimes they have similar backgrounds, sometimes they do not. And when you jump into this new version of you, you are both yourself and the version of you whose body it is. That’s what Adam Sandler does. Each new movie, he is the collections of self he’s acquired along the way, as well as the person he is in the given movie. When zoomed out, the result is a portrayal not of a collection of similar characters but the total soul of the archetype.

2. The Wedding Singer (1998)

Adam finds his equal and a more mature version of himself.

When Adam Sandler appeared on Norm Macdonald Live, the host posited a theory about why Sandler and Drew Barrymore were so good in romantic comedies together. “You are both children,” he said in his signature deadpan. “You are both ageless, so you seem like a little boy and she seems like a little girl.” I wouldn’t say the phrasing is ideal, but it is insightful. Sandler and Barrymore share a similar childlike innocence that can be very useful for this particular genre. Traditional romantic comedies simplify what it’s like to fall in love, trying to capture the feeling without getting bogged down by adult obligation. It’s exciting to see people who just dive in wholeheartedly, free of neurosis. When Sandler and Barrymore fall for each other, no matter how old their characters are in the given movie, it feels like young love. And The Wedding Singer, opposed to their other collaborations, doesn’t put as much plot in the way of their chemistry. Even years later, it’s hard to not be charmed watching these two sweeties at the height of their powers.

Ironically, this was Sandler’s most mature work to date, if not ever. Comedically, he’s strong, but instead of his lowbrow/annoying instincts, you get clever ’80s jokes (pioneering a cottage industry of ’80s reference comedy). And it’s incredible how good he is in this. It’s our first glimpse of him as an actual actor. He’s particularly good at being present with Barrymore and having the story play on his face. It helps, of course, that Barrymore is great and is given a ton to do. Carrie Fisher famously did a major rewrite of the original script (Sandler and Apatow eventually did a similarly uncredited pass afterward), which was based on Sandler’s idea of wanting to make a movie set in the ’80s and to play a wedding singer who got left at the altar. Fisher beefed up the female lead’s part, and its apparent onscreen, where Barrymore feels like her own person with agency, as opposed to a prop for Sandler’s story (something that has held true for all of Barrymore-Sandler movies).

It’s the only other movie I considered to top this list. When you watch those three breakout films in a row, Wedding Singer feels like the fully evolved form. Even the way the character grows up feels more complicated, more subtle. Over the course of the movie, Sandler and Barrymore must both overcome their naïveté while also not being corrupted by the cynicism of the real world. To take this a step further, the movie is about rejecting what you’re told you’re supposed to want for what really matters. Arguably, the film is a sly satire of ’80s yuppies and the baby-boomers who abandoned their values to chase the stock market.

But it still didn’t feel right to put it at No. 1. I remember going to see The Wedding Singer in the theaters, as a bit of a relief from the pressures of studying for my bar mitzvah. Of course, I was excited. This was an Adam Sandler movie! I never told anyone this, because I guess I didn’t know if it was okay to not like movies you paid to see, but I was sort of meh on it — rapping granny be damned. Now, over the years of rewatching and getting older, I’ve grown to love it; however, I can’t help but think there’s something to little baby me’s reaction. You watch every Adam Sandler movie and there is a clear value system. And Wedding Singer, when judged by that measurement, comes up a tiny bit short. There ar