Adam Sandler's 10 Best Movies, Ranked
After winning legions of fans with his appearances on SNL at the beginning of the ‘90s, Adam Sandler’s ascendance to Hollywood star was incredibly smooth.
The actor’s early string of hits, a run that started with Billy Madison in 1995, quickly turned him into one of the most bankable comedy talents in the world. A few years later, after conquering that corner of the moviesphere, he started to take the occasional side quest into more dramatic roles and soon found critical acclaim while working with some of the best American filmmakers of his generation.
In more recent years, bolstered by a big-money deal with Netflix, the actor’s output has been streamlined into those two distinct categories: comfort food comedy (increasingly and touchingly featuring members of his own family) that lots of people see, and the occasional dramatic flourish to remind everyone what he’s capable of. His recent turn in Noah Baumbach’s Jay Kelly once again put him in the awards conversation, so it feels as good a time as any to round up the Sandman’s 10 best movies, which I’ve listed below in ascending order. Read on to discover more and use the guide below to find them on Apple TV, Netflix, Prime Video and elsewhere.
Grown Ups is the kind of Sandler movie that will either seem like a baffling mess or a nostalgic gem, depending on how old you were (or your kids were) when it came out. This old-dudes buddy-comedy saw Sandler reteam with his Happy Gilmore director Dennis Dugan and some of his oldest comedy pals—Kevin James (Paul Blart), David Spade (The Benchwarmers) and Chris Rock (The Longest Yard)—meaning the vibe could hardly be more relaxed and genial.
Released in 2010, this was Sandler’s first mega-hit comedy in a good few years, and even if the critics panned it at the time, it didn’t fail to deliver—earning four times its budget at the box office and prompting an equally successful sequel in 2013.
If you enjoy Sandler’s chaotic outbursts but appreciate his softer side, too, Big Daddy offers the best of both worlds. The story sees Sandler play Sonny Koufax, a thirty-something-year-old man who adopts a five-year-old boy in order to show his ex-girlfriend that he can be a responsible adult. Naturally, it doesn’t go to plan.
The movie came a year after The Waterboy, which was and still is the actor’s most successful movie by some metrics. Big Daddy didn’t quite hit those numbers (it wasn’t far off), but it’s significant in the actor’s career as, similar to The Wedding Singer, it showed he had the potential to play more sensitive roles.
Sandler had appeared in Coneheads in 1993, but his first big-screen success came a couple of years later. This is a movie that was so important to him that he literally named his production company after it—albeit combined with another movie on this list.
Billy Madison—in which Sandler plays a rich kid forced to re-sit every grade in school over the course of a month—is exactly the kind of fish-out-of-water comedy that would define the next decade of Sandler’s movie career. If you like his vibe on SNL or appreciate other back-to-school comedies like 21 Jump Street, you’ll probably dig it.
Given all his wealth and success, it’s remarkable how humble Sandler appears in interviews. That said, you wouldn’t hold it against him for wondering what he needs to do to get an Oscar nomination at this stage—something that’s been eluding him for the last 20 years now, despite a few more than worthy attempts.
Sandler’s latest swing for awards season recognition was a supporting role in Noah Baumbach’s slightly bumbling but mostly sweet Jay Kelly, in which the actor plays the long-suffering handler and manager of George Clooney’s titular star, who is (similar to movies like Somewhere and Birdman) presented as a heightened and slightly surreal version of Clooney himself. The film put Sandler in the running for a 2026 Best Supporting Oscar nod, which turned out to be a fiercely competitive category.
If you appreciate a good sports drama, Sandler’s 2022 movie Hustle ticks all the right boxes for the genre. The story follows an NBA scout (Sandler) who discovers a rough diamond in Spain (played by Juancho Hernangómez) and decides to bet his career on trying to nurture him for the big leagues—think recent B-ball movies like High Flying Bird or The Way Back, and you’ll get the idea.
Like a lot of Sandler’s dramatic work, Hustle is a labour of love, but it’s also backed by some of the most influential names in the sport—Lebron James is one of the producers, and the cast is littered with big-name cameos like Luka Dončić and Shaquille O’Neal.
The other movie that Sandler used to name his production company, Happy Madison, is the 1996 sports comedy classic Happy Gilmore. This is the one where Sandler plays a wannabe hockey pro who takes up golf in order to help his grandmother keep her home, becoming an unlikely fan favourite as a result. If you’re a fan of movies like DodgeBall or Blades of Glory, this one will be right up your street.
I’ve chosen this one as the best Sandler movie from that era because it’s still hilarious, but also because of its incredible legacy—just check out the number of famous people who agreed to cameo in the recently released (and actually half-decent) Netflix sequel, and you’ll see what I mean.
It’s fair to say that not everyone knew what to make of Funny People when it was released in 2009. The movie had promised the dream team pairing of the most influential comedy person of that decade, Judd Apatow (Anchorman, 40 Year Old Virgin, Superbad) and Sandler, the most influential comedian of the previous one. Instead, we got an almost surreal exploration of fame and a story about a man’s midlife crisis.
Since then, the movie’s reputation has only gone from strength to strength and is now rightly considered to be one of the best movies in both Sandler's and Apatow’s careers. If you want to see two artists so on top of their game that they almost seem to be on autopilot, this might be right up your street.
Like Jay Kelly, The Meyerovitz Stories (New and Selected) is not among Noah Baumbach’s best works. Also, like Jay Kelly, Sandler is the best thing about it. The actor plays one of three siblings (alongside Ben Stiller and Elizabeth Marvel) who reunite for a ceremony to celebrate their artist father’s work. The acting is top tier across the board, but it’s Sandler’s easy chemistry with Grace Van Patten—who plays his daughter Eliza—that gives the movie its beating heart.
The actor is now more known for his dramatic work, but at the time of Meyerovitz’s release, these kinds of roles were few and far between—which is why it felt so precious. If you liked Marriage Story or The Squid and the Whale, you’ll probably be just as into this one.
The last two titles on this list are both so different and both so good that it feels vaguely sacrilegious to choose between them. On another day, Paul Thomas Anderson’s Punch-Drunk Love could easily top the chart—especially given how Anderson was the first to spot Sandler’s untapped dramatic potential. It’s also not a stretch to suggest that the next movie on this list might not exist without it.
Regardless of all that, Anderson’s first movie post Magnolia remains a strange outlier in the director’s back catalogue—a genuinely sweet and unnerving romantic comedy that’s unlike any other movie in the genre. If you appreciate Anderson’s work pre-There Will Be Blood (think Hard Eight, Boogie Nights) and are also a fan of Philip Seymour Hoffman in full scumbag mode, you will absolutely love it.
You could hardly swing a cat at the cinema in the last few years without hitting a Safdie brother—Benny acted in both Oppenheimer and Happy Gilmore 2 before directing his first solo effort (the underappreciated The Smashing Machine) last year. Josh, meanwhile, is currently getting hyped to the heavens for his Chalamet-led Oscar hopeful, Marty Supreme. 2019’s Uncut Gems, however, remains the siblings’ greatest achievement—proof, perhaps, that they’re at their best when working together.
Uncut Gems wears its influences on its sleeve, but it is nothing but unique: an experience that’s nerve-shredding and cosmic in equal measure, and one that offers a thrilling mishmash of heist movie style and sports movie excitement. At its heart, however, it’s a character study about Sandler’s gambling addicted diamond trader, Howard Ratner—a role that would be hard to imagine without his explosive charisma. It’s still the best thing he’s ever done.
