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Nothing divides an audience like Adam Sandler: there are those who regard him as a Chaplinesque comedic genius, and those who think his very existence is an insult to the craft of filmmaking itself. Almost every time he makes a film (and he does so more often than many other famous folks), we're reminded that the man responsible for Happy Gilmore and Punch-Drunk Love might just...not be all that interested in making movies like those anymore. That was the case until this week’s Uncut Gems (a Safdie Brothers instant classic), which relies on Sandler’s talent for playing underdogs—his Howard Ratner is scrappy and resilient, cracking jokes and taking punches on the chin. And like the very best films he’s made, this one understands his knack for absolutely committing to the absurd.
But that doesn't change the fact that Sandler's career is long and...varied, full of great films, mediocre films, and a few outright terrible ones. Hell, this very magazine took his filmography to task not five years ago. Sandler being Sandler, that list has grown, and it's time for a reassessment, so I sat down for a very long trip through the Sandman's filmography. Time has not been kind to some of his earlier work, and some of his later work for that matter, but any child of the '90s knows that Billy Madison is not to be trifled with.
NB: I’ve excluded all short films, documentaries and uncredited cameos, mainly for my own sanity.
48. The Animal
You know what is categorically, unequivocally worse than any Adam Sandler film? Any Rob Schneider film.
47. The Zookeeper
Trivia time: Adam Sandler has played characters called Donald three times. In The Zookeeper, he voices a capuchin monkey called Donald.
46. Going Overboard
This was Sandler's first film, in which he combined a cruise ship full of scantily-clad women, stand-up comedy, and terrorism. It is extremely unfunny but did at least bring him to the attention of the Saturday Night Live team, so it was good for something, I guess.
45. The Ridiculous 6
Puerile and offensive in its outdated stereotypes, this is quite easily the worst movie Sandler's made under his (since-2014) Netflix deal.
44. Eight Crazy Nights
An animated, Hanukkah-themed musical comedy sounds cute! Unfortunately, it's not—probably because Adam Sandler decided to voice just about every character, for reasons I do not fully understand.
43. Men, Women & Children
Jason Reitman said “We live in a society” with this 2014 cynical reflection on how modern technology has shaped human interaction. Everyone ignored him.
42. Mixed Nuts
Sometimes at night, I lie awake thinking, “How did Norah Ephron go from making Sleepless in Seattle to this?”
They really were just letting SNL do anything they wanted in the early ‘90s.
For anyone who’s ever wondered why Adam Sandler didn’t make more action movies, here is your answer.
My least favorite of the Sandler romcoms, if only because of how old-fashioned it is. Sandler and Drew Barrymore aren’t even pretending to not phone it in, but at least they got a South African vacation out of it.
38. That’s My Boy
In a rather serious disappointment, Andy Samberg and Adam Sandler made a film together and all we got were jokes about statutory rape.
It’s mind-blowing this film was made in 2015, because it ripples with such powerful mid-'90s vibes. The casual sexism, the aggressive Gen X nostalgia, the off-putting bro-centric humor… none of it makes for particularly exciting viewing, even to someone who loves video games.
36. The Longest Yard
Even if you're a football fan—I'm British, and not—there are enough off-color prison jokes to push this into don't-watch territory.
35. 50 First Dates
A plot that seemed romantic upon release has curdled into something closer to creepy.
34. Grown Ups 2
The best thing about this film is the poster. Is Kevin James…hot?
33. I Now Pronounce You Chuck & Larry
A compelling argument for universal healthcare, if not for cinema.
32. Bedtime Stories
Weirdly, Adam Sandler and fellow SNL alumnus Eddie Murphy released films with very similar premises in 2008, about men whose lives are changed due to imaginary children's stories coming to life. Bedtime Stories isn’t whimsical enough to be charming, and despite being pitched as a kid’s movie, goes surprisingly heavy on the contrived romance subplot. At least Keri Russell and Sandler are good together.
31. Grown Ups
It’s the middle-aged adaptation of Jackass that no one asked for, but I respect the hustle of making a feature film so you get to hang out with your friends for a few weeks.
30. Hotel Transylvania 2
I remember very little about this film other than the fact Mel Brooks plays Dracula’s father, Vlad.
29. Hotel Transylvania 3: Summer Vacation
That said, my secret pleasure is the Hotel Transylvania series, and while this isn't a Godfather Part II situation, I did enjoy Joe Jonas's role as a singing Kraken. Pirates of the Caribbean could never.
28. Sandy Wexler
There’s a great premise at the heart of Sandy Wexler: a well-meaning but failing Hollywood talent agent finally lands a client with actual talent (played by none other than Jennifer Hudson) and goes to great lengths to get her the recognition she deserves. It’s let down by a bloated script and Sandler’s most irritating on-screen accent to date—quite an achievement in such a crowded field.
27. Shakes the Clown
Martin Scorsese called this "the Citizen Kane of alcoholic clown movies," which cannot be improved upon.
26. Little Nicky
This was the first Adam Sandler film I ever saw, and I watched it so much I broke the VHS tape. It hasn't aged well (Hitler jokes, a terrible talking dog, that particularly awful Sandler haircut) but personal bias requires me to show it some affection. Harvey Keitel as the Devil? Perfection.
25. The Cobbler
Features a very handsome Dan Stevens, but I couldn’t stop thinking about the fact that the year after Tom McCarthy made this (quite bad!) film, he won an Oscar for Spotlight.
The concept of Brendan Fraser, Adam Sandler, and Steve Buscemi in a rock band together exudes a powerful chaotic energy.
23. The Do-Over
Contains a through-line about how American pharmaceutical companies conspire to keep effective drugs off the market if they threaten profits, which is a wild plot point for a Sandler movie, but one I totally respect.
22. You Don't Mess with the Zohan
A film in which Adam Sandler—playing a member of the IDF turned renowned hairdresser—solves the Israeli/Palestine conflict. Sure!
21. Happy Gilmore
Men love quoting this film to me and I’ve never fully understood why.
20. The Week Of
Adam Sandler and Chris Rock team up for this low-key culture-clash comedy, playing the fathers of a young couple about to get married. I very much enjoyed seeing Sandler and Rachel Dratch yell at each other for two hours.
19. Jack and Jill
Routinely dismissed as the worst Adam Sandler film due to Sandler’s cross-dressing and how irritating his Jill character is, but Jack and Jill actually features Al Pacino giving the most Al Pacino performance of all time, so it's good. I’m happy to die on this hill alone.
James L. Brooks cast Sandler in this romantic drama about literal and metaphorical failure to communicate after watching him in Punch-Drunk Love. Sandler is charming enough as the easygoing albeit clueless chef John Clasky, but the real star is 12-year-old Shelbie Bruce, playing the daughter of Paz Vega’s nanny/housekeeper Flor. Bruce absolutely shines in a scene where she has to act as a translator for her mother and John during an argument.
17. Hotel Transylvania
It’s no Shrek, but like I said, this kids' movie is pretty cute. I particularly enjoy Steve Buscemi as perpetually harried werewolf Wayne. The Sandler/Buscemi friendship is one of Hollywood’s most enduring; after hitting it off on the set of Airheads back in 1994, they’ve gone on to make 13 more films together, and he’ll pop up again in next year’s Hubie Halloween.
16. The Waterboy
I still don’t understand football, but I do understand that this is possibly the most earnest film ever made—a classic Revenge of the Nerds-style underdog story, in which he plays stuttering, socially-inept Bobby Boucher, who’s promoted from waterboy to linebacker, channeling years of pent-up aggression into his game. The biggest coup was getting Academy Award-winner Kathy Bates to play Sandler’s overbearing mother—the story goes that she wasn’t interested, and her agent didn’t want her to take the role, but Bates’s niece (a Sandler fan) convinced her to reconsider. Thank you, Kathy’s niece, for your service.
15. Top Five
Sandler has a small cameo as himself in his buddy Chris Rock’s movie about a New York comedian and actor who begins to reevaluate his career and life choices after an encounter with a journalist. A stellar cast, quick-fire pace and sense of self-awareness about Top Five make it a genuinely great film, meditative on the nature of fame, love, and selling out without being self-indulgent. Plus, it confirms who Jerry Seinfeld’s favorite hip-hop artists are. Finally.
The popular critique of Click upon release was that it was emotionally manipulative. They were just mad Adam Sandler made them cry. Yes, it's shamelessly cribbed from It's A Wonderful Life, and yes, the fat suits were completely unnecessary, but Sandler is surprisingly effective as an overworked father struggling to remember what’s important in life – and Jake “Son of Dustin” Hoffman is hot, so I'm giving it a pass.
13. Reign Over Me
Mike Binder’s drama saw Sandler play a grief-stricken man who lost his entire family on 9/11 and turns to an old college friend (Don Cheadle) for support. It’s often overlooked in his oeuvre, which is a shame given that Sandler puts his all into the performance, trading his usual gurning and shouting for abject sorrow as a man whose world has totally collapsed. Many films that deal with the aftermath of the Twin Towers attacks feel exploitative (looking at you, Remember Me), Reign Over Me is sincere and genuinely moving, in no small part thanks to Sandler’s committed performance.
12. Murder Mystery
Murder on the Orient Express (2018) wants what Murder Mystery (2019) has. Glamorous location? Check. Beautiful, terrible characters being dicks to each other? Check. Jennifer Aniston in a red dress and Adam Sandler with a tiny mustache, riffing on all the classic tropes of Agatha Christie and Alfred Hitchcock? Kenneth Branagh could never.
11. Just Go with It
Jennifer Aniston and Adam Sandler have great chemistry together—so much so that they elevate this otherwise cliche rom-com about realizing the person you’re meant to be with has been in front of you the whole time. Aniston plays the long-suffering assistant to Sandler’s womanizing plastic surgeon, and in the film’s best scene, recalls with ease all the small details about him she’s gleaned from years working together. All the small details you only really notice when you care about someone. Aw. It also features Nicole Kidman doing a hula dance, which is a delightful sight.
10. Mr Deeds
Plenty of Sandler skeptics find it difficult to believe any of his films contain an ounce of social commentary, but Mr. Deeds perhaps comes closest. In this remake of Frank Capra’s 1936 Mr. Deeds Goes to Town, Sandler plays a small town everyman who inherits a vast fortune from a distant relative. There’s slapstick violence, John Turturro saying “Shneaky shneaky” and corny greetings card poems, but Mr. Deeds is one of Sandler’s sweetest, least outlandish turns to date. There’s no grating accent, a minimal amount of gross-out humor, and Sandy Cohen himself (Peter Gallagher) in top form as the nefarious businessman out to steal Deeds’s fortune.
9. The Meyerowitz Stories (New and Selected)
Noah Baumbach's film yielded one of Sandler's most traditional, regular-actor-actually-trying performances in recent years. The singer of "The Hanukkah Song" has the range!
8. Anger Management
Another widely-derided Sandler film which is more fun than people think: Jack Nicholson has a blast playing the most annoying therapist in the world, there's an adorable fat cat called Meatball who wears a hoodie, and at the end, Sandler sings “I Feel Pretty” from West Side Story. It's fun!
7. Funny People
Sandler plays a successful but disillusioned stand-up comedian/actor recently diagnosed with leukemia in Judd Apatow’s dramedy. It’s the rare instance of Sandler taking work that makes use of his reputation, and one that reminds us he's more than capable of performing dramatic roles. Also features an alarmingly funny moment between Sandler and Eminem, of all people.
6. Adam Sandler 100% Fresh
Sandler returned to stand-up for the first time in 15 years for this Netflix comedy special, and it was worth the wait. There’s jokes, there’s songs, there’s Rob Schneider dressed as an astronaut dangling from the ceiling while singing about fellatio. Most importantly, at a time when many old school comics have failed to move with the times, Sandler’s show doesn’t punch down. He’s the butt of most jokes, and combines lowbrow humor about bodily functions with wonderfully esoteric bits on a life-long desire to do a backflip and a revelatory trip to Disneyland. That’s without even mentioning his heartfelt tribute to Chris Farley.
5. The Wedding Singer
The first and undoubtedly best Sandler rom-com, with an extremely good Cure-heavy soundtrack and a very fun Billy Idol cameo. Drew Barrymore is adorable, Sandler is adorable, and the climactic rendition of “Growing Old With You” is so sweet it gives me cavities.
4. Billy Madison
The film that arguably started it all. Billy Madison is probably the best showcase of Sandler’s flair for the ridiculous. He faces off against a young and nefarious Bradley Whitford) in Tamra Davis’ comedy about an entitled slacker reentering the public education system to prove his worth. The most charming part of the film is seeing the way Sandler acts with kids—the old adage goes, "Never work with children or animals," but Sandler has turned both into an art form, more than willing to indulge in pratfalls and silliness in the name of performance. Billy Madison was the original man-child, and his transformation in the film might now be the stuff of Hollywood cliché, but at the time, Sandler was a renegade oddball. He did for silliness what Warhol did for soup cans.
3. Uncut Gems
Josh and Benny Safdie are serious Sandler fans, and spent 10 years trying to convince him to star in their movie. It was worth it: as Diamond District jeweler Howard Ratner, Sandler a ball of chaotic energy, pinging around the Big Apple wheeling and dealing as he attempts to keep various debtors at bay. He’s already won a swath of great reviews and prizes for his performance and might soon receive his first Oscar nomination, but anyone who knows Sandler’s back catalogue will be able to trace the path from his comedy origins to this extraordinary, exhilarating New York runaround.
2. Big Daddy
Yes, there’s toilet humor, and it’s not exactly an original premise, but Big Daddy combines Sandler’s talent for physical comedy with his sometimes forgotten softness. He plays a slacker who adopts an adorable child in a misguided effort to win back his girlfriend, but slowly becomes quite fond of the wee kid, played by Disney favorites Dylan and Cole Sprouse. It’s sweet, funny, and sometimes kind of gross—in other words, it's similar to both parenthood and the very best Adam Sandler movies.
1. Punch-Drunk Love
There was only ever one film that could top this list. Paul Thomas Anderson’s spin on the rom-com saw Sandler take his first dramatic role as harried salesman Barry Egan, who wears ill-fitting suits and obsesses over a scheme to turn chocolate pudding into airline miles. In a recent Actors on Actors conversation with Brad Pitt, Sandler credits Paul Thomas Anderson with making him believe he could pull off a dramatic role, but it’s impossible to imagine anyone else as the downtrodden, desperate Barry, channeling the impotent rage Sandler made his art into something more finessed. This tender exploration of love and loneliness is an ode to weirdos—which, when you really think about it, could be said of Sandler’s filmography more generally. He’s always marched to the beat of his own drum, happy to do what makes him happy. Sandler didn’t come here to win everyone over. He just came out to entertain.
Originally Appeared on GQ