The best movies of Adam Sandler, the Sandman himself and the fashion prince trying to single-handedly bring gigantic basketball shorts back into the world, see him wear a lot of hats. After cutting his teeth as a musical weirdo on SNL, he went on to forge a unique on-screen identity as a surreal and fratty man-baby in a string of hit lowbrow comedies. Happy Madison Productions would never reclaim the novelty of Sandler’s weird voices or its ‘90s power, but Sandler would—by going dramatic. His underrated acting abilities (even in films like Reign Over Me) would serve him well, leading to a critical career revival in Uncut Gems. This countered an increasingly tepid series of comedies that involved the same group of actors failing to convince us that they give a damn in a variety of exotic locales. Sandler seems just as happy making both kinds of movies, but we’re mostly happy he’s willing to take any risks at all considering how stable his comic formula seems to be. We’re still hoping for more of those envelope-pushing roles from the performer, especially after seeing what he’s really capable of. In the words of Rob Schneider’s various characters, “You can do it!”
Today we take a look at the 10 best Adam Sandler movies:
10. Hubie Halloween
Year: 2020
Director Steven Brill
Stars: Adam Sandler, Kevin James, Julie Bowen, Ray Liotta, Rob Schneider, June Squibb, Kenan Thompson, Shaquille O’Neal, Steve Buscemi, Maya Rudolph, Tim Meadows, Karan Brar, Paris Berelc, Noah Schnapp, China Anne McClain, Michael Chiklis
Rating: PG-13
Runtime: 102 minutes
Perhaps apocryphal, Adam Sandler’s promise/threat to follow up an Uncut Gems Oscar snub with a new movie “so bad on purpose just to make you all pay” (as he told Howard Stern a year-or-so ago) may have come to collect with the ostensibly dumb Hubie Halloween. After all, if this is punishment, we deserve this, right? But somehow, despite history and common sense demonstrating otherwise, Steven Brill’s seasonal ode to the Sandman’s baby voice is as much a disarmingly, genuinely sweet endeavor as it is a rehabilitation of Sandler’s earliest successes—Billy Madison and Happy Gilmore especially, what with the cameos by a McDoyle and Ben Stiller as a vindictive orderly—once-beloved movies that haven’t so much aged poorly as just feel like they belong to a different lifetime entirely. Nostalgia may make for cheap bait in a pandemic, but amidst the predictable appearance of all of Sandler’s friends and the insistence that no matter how pathetic a titular Adam Sandler character can get, many wonderful women will always, against all odds, love him fiercely, Hubie Halloween exorcises many of the mean-spirited ghosts that have haunted his canon. So goes the story of a grown man named Hubie (Sandler) who lives with his mother (June Squibb, lovely) and, obsessed with Halloween, takes it upon himself to make sure the denizens of Salem, Massachusetts celebrate safely every year, even though they resent him so much they throw increasingly unwieldy objects at him wherever he goes. The movie’s bloated with physical gags, often at the expense of Hubie’s face, nards and/or dignity, and flush with character actors seemingly having a blast. There’s Ray Liotta, game for getting typecast as “loudmouthed lech”; there is Michael Chiklis, his head a thumb. Shaq is here, and so is Steve Buscemi, and Maya Rudolph, and Kevin James; even Rob Schneider, typically execrable, is used sparingly, responsible for one of the movie’s funniest lines, a line that is about peeing himself. All are deployed throughout a thoroughly low-stakes plot, in which everyone learns to treat Hubie with a modicum of dignity, but rather than ring as trite and unearned, Hubie Halloween’s got 25 years of similar movies behind it—two and a half decades of cinema whose worst sin is giving all of Adam Sandler’s friends an excuse to celebrate their friendship. You may have reached your limit with that voice, and no one would blame you, but it’s hard to deny that a sweetly dimwitted movie with a simple message about taking care of one another is probably more than we deserve in 2020. —Dom Sinacola
9. Anger Management
Year: 2003
Director Peter Segal
Stars: Adam Sandler, Jack Nicholson, Marisa Tomei, Luis Guzmán, Woody Harrelson, John Turturro
Rating: PG-13
Runtime: 106 minutes
Adam Sandler’s steady downward slide was momentarily halted almost entirely because of Jack Nicholson. The Hollywood legend unleashed his malevolent side as an unconventional therapist helping Sandler overcome his rage issues. Nicholson’s charisma—and the perverse appeal of seeing him in such a low stakes, low brow comedy—is a fine antidote to the increasing laziness of the Sandler formula. Nichoson’s not the only legitimately great actor in this movie—in addition to talented Sandler regulars like John Turturro and Luis Guzman, the cast also includes Woody Harrelson, Harry Dean Stanton, John C. Reilly, and, in a true coup, acting legend Rudy Giuliani.—Garrett Martin
8. Hotel Transylvania
Year: 2012
Director Genndy Tartakovsky
Stars: Adam Sandler, Andy Samberg, Selena Gomez, Kevin James, Fran Drescher, Steve Buscemi, Molly Shannon, David Spade, CeeLo Green
Rating: PG
Runtime: 91 minutes
Though dismissed by some as yet another juvenile Adam Sandler vehicle (only this time with an eye towards kiddie audiences), Hotel Transylvania delivers to a surprising degree, displaying a buoyant giddiness and nonstop energy that is utterly infectious. Much of this could be attributed to the work of animation god Genndy Tartakovsky (he of Samurai Jack, Powerpuff Girls and Dexter’s Lab fame). The gags come as hard and fast as any Zucker-Abrahams-Zucker production, with many cast members doing some of their best comedic work in years. Though perhaps overly exhausting and annoying for some, Hotel Transylvania displays an ambition and dedication to its craft that feels sorely lacking in many mainstream theatrical movies aimed at children. —Mark Rozeman
7. Funny People
Year: 2009
Director Judd Apatow
Stars: Adam Sandler, Seth Rogen, Leslie Mann, Eric Bana, Jonah Hill, Jason Schwartzman
Rating: R
Runtime: 146 minutes
It’s gotten the reputation as the beginning of Judd Apatow’s overlong, navel gaze-y period, but Funny People is really him trying to step into the shoes of his hero James L. Brooks, making the kind of dramatic comedies that simply don’t get made anymore. Following a younger comic (Seth Rogen in a UCB shirt) assisting an Adam Sandler-esque movie star (…Adam Sandler) who is dying of cancer, Funny People is a meditative hang-out comedy that nails the clash between generations of comedians and the seeming futility of comedy in the face of death. It’s worth a second look.—Graham Techler
6. The Meyerowitz Stories (New and Selected)
Year: 2017
Director: Noah Baumbach
Stars: Adam Sandler, Dustin Hoffman, Ben Stiller, Elizabeth Marvel, Emma Thompson, Candice Bergen, Adam Driver, Sigourney Weaver
Rating: R
Runtime: 112 minutes
In maybe his most well-tuned chamber drama (let’s use this phrase loosely) since Frances Ha, Noah Baumbach takes time to observe the ways in which his characters run, their ambulatory gifts (or lack thereof) representing both their struggles to express their innermost selves and the ways in which they can’t escape the parents who must pass themselves—their failures, their quirks, their anger—to their offspring. One gets the sense that Baumbach wants to literalize the act of “running from” one’s deepest problems, but such tracking shots are largely played for laughs: Family patriarch Harold Meyerowitz (Dustin Hoffman), a sculptor seeking acknowledgement in his old age, shuffles dopily down New York’s streets; Matt Meyerowitz (Ben Stiller) possesses the grace of a well-used corporate gym membership; Danny Meyerowitz (Adam Sandler, deserving of an Oscar) hobbles around denying that he’s got a major medical problem; and Jean Meyerowitz (Elizabeth Marvel) just seems like she shouldn’t be running, Matt and Danny at one point consorting about how they’ve never actually seen her run before. In these moments, Baumbach allows the cerebral to awkwardly take on corporeal life, wondering aloud how the many themes and ideas we conceptualize (and thus internalize) break free in some sort of physical melee. It’s his tennis scene in The Squid and the Whale made feature length—and it may be the most viscerally moving film he’s ever made. —Dom Sinacola
5. Happy Gilmore
Year: 1996
Director: Dennis Dugan
Stars: Adam Sandler, Christopher McDonald, Julie Bowen, Frances Bay, Carl Weathers
Rating: PG-13
Runtime: 92 minutes
Adam Sandler could’ve retired in 1998, after his first three movies, and his comedy legacy would’ve been secured. (He maybe should’ve retired then, but let’s not get into that.) It’s hard to pick between The Wedding Singer, Billy Madison and Happy Gilmore, but let’s talk about that last one right now. The tale of a failed hockey player becoming a champion golfer is an ideal vehicle for Sandler’s inchoate frat boy rage, and the absurd streak that elevated Madison above most Hollywood comedies of the day is even more visible here. It has some of the same problems as most Sandler movies—an underwritten, unbelievable love interest (here played by Modern Family’s Julie Bowen), a bare bones story that’s little more than a launching pad for jokes—but Gilmore is an ideal character for Sandler, and a great supporting cast (including Carl Weathers, Ben Stiller, Richard Kiel, Joe Flaherty, and Christopher McDonald as the iconic villain Shooter McGavin) help turn this into a legitimate classic. Also there’s a great chance this is the main thing younger people know Bob Barker from, which is actually kind of sad.—Garrett Martin
4. Billy Madison
Year: 1995
Director: Tamra Davis
Stars: Adam Sandler, Darren McGavin, Bridgette Wilson-Sampras, Bradley Whitford, Norm MacDonald
Rating: PG-13
Runtime: 89 minutes
There’s a strong case to be made that Billy Madison is the best Adan Sandler movie. Sure, it’s not as human as The Wedding Singer, and it’s hard to vote against Happy Gilmore, but Madison so thoroughly exceeded the abominably low expectations I had for it in 1995 that it wound up being one of the most memorable movies of the decade. It’s still hilarious today, a perfect vehicle for Sandler’s man-child persona, and one that surrounds him with a fantastic supporting cast, including Bradley Whitford, Darren McGavin, Norm Macdonald, Chris Farley, and a giant penguin, among others. It’s not the story or even the jokes that make Billy Madison so funny—it’s the surreal flourishes, the way lines are delivered, how Tamra Davis (both a woman and an outsider to the small circle of men who have directed most of Sandler’s movies since) is able to contrast Sandler’s weirdness with a world that feels recognizable in its everyday mundanity. Later Sandler movies feel lazy and untethered from the real world, but Madison doesn’t suffer from either flaw. It’s dumb comedy done with enough weirdness and intelligence to become a true classic.—Garrett Martin
3. Punch-Drunk Love
Year: 2002
Director: Paul Thomas Anderson
Stars: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzman
Rating: R
Runtime: 95 minutes
It may be hard to recall now that we’ve all rallied around his talent—allowing him to transcend the stigma of his Netflix deal while he still profits ludicrously off it—but there was once a time when the world doubted Adam Sandler. Long before the Safdies or even Noah Baumbach got their time getting tight with the Sandman, we have P.T. Anderson to thank for inspiring such hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, or the obsession and obfuscation of Phantom Thread, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize, and complicate, with Inherent Vice. A simple love story between a squirmy milquetoast (Sandler) on the verge and the woman (Emily Watson) who yanks him back to life, Punch-Drunk Love is as confounding as it is a delight, an expression of unmitigated, sputtering passion—sad and febrile and, most importantly, optimistic about what anyone is truly capable of doing. This might be as sincere as Anderson gets. —Dom Sinacola
2. The Wedding Singer
Year: 1998
Director: Frank Coraci
Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert, Matthew Glave
Rating: PG-13
Runtime: 96 minutes
Over 20 years removed, Frank Coraci’s vision of the mid-’80s by way of the late-’90s bears the pastel aesthetic and pop culture refuse of a parody of that decade more than a clear memory of what was actually going on, but all the better to ground the then-popular caricature of Adam Sandler in a tender role best suited to his natural baby-man weirdness. What Happy Gilmore and Billy Madison did for Sandler’s “stop looking at me swan” voice, The Wedding Singer did for every other aspect of the comic actor, not only mitigating all that past frat boy dipshittery, but demonstrating that he could be a quiet, lovable leading man—a persona he’d go on to hone with his best films (notably, Punch-Drunk Love and The Meyerowitz Stories). The story of a banquet hall’s in-house crooner, Robbie Hart (Sandler), suffering a broken heart (like his name!) to find his way to the true girl of his dreams (Drew Barrymore, simultaneously endearing and cloying) hits each rom-com beat so squarely it’s nearly impossible to not see where this thing is going, but its heady brew of ultra-nostalgia and surreal poptimism, as well as Sandler’s unforced hilarity, serves the genre beautifully. The movie’s only glaring miscue is the repeated lambasting of Robbie’s bandmate George (Alexis Arquette), who navigates an onslaught of audience booing every time he sings Culture Club’s “Do You really Want to Hurt Me?” Since the movie takes place in 1985, the song’s been a certifiable hit for more than two years. The audience’s revulsion is more of a cheap gag than a cultural reality, a misremembered joke from a manufactured history—like much of the ’80s of The Wedding Singer, as dated today as it was in 1998. —Dom Sinacola
1. Uncut Gems
Year: 2019
Directors: Josh Safdie, Benny Safdie
Stars: Adam Sandler, Julia Fox, Eric Bogosian
Rating: R
Runtime: 135 minutes
The proprietor of an exclusive shop in New York’s diamond district, Howard Ratner (Adam Sandler) does well for himself and his family, though he can’t help but gamble compulsively, owing his brother-in-law Aron (Eric Bogosian, malevolently slimy) a substantial amount. Still, Howard has other risks to balance—his payroll’s comprised of Demany (Lakeith Stanfield), a finder of both clients and product, and Julia (Julia Fox, an unexpected beacon amidst the storm in her first feature role), a clerk with whom Howard’s carrying on an affair, “keeping” her comfortable in his New York apartment. Except his wife’s (Idina Menzel, pristinely jaded) obviously sick of his shit, and meanwhile he’s got a special delivery coming from Africa: a black opal, the stone we got to know intimately in the film’s first scene, which Howard estimates is worth millions. Then Demany happens to bring Kevin Garnett (as himself, keyed so completely into the Safdie brothers’ tone) into the shop on the same day the opal arrives, inspiring a once-in-a-lifetime bet for Howard—the kind that’ll square him with Aron and then some—as well as a host of new crap to get straight. It’s all undoubtedly stressful—really relentlessly, achingly stressful—but the Safdies, on their sixth film, seem to thrive in anxiety, capturing the inertia of Howard’s life, and of the innumerable lives colliding with his, in all of its full-bodied beauty. Just before a game, Howard reveals to Garnett his grand plan for a big payday, explaining that Garnett gets it, right? That guys like them are keyed into something greater, working on a higher wavelength than most—that this is how they win. He may be onto something, or he may be pulling everything out of his ass—regardless, we’ve always known Sandler’s had it in him. This may be exactly what we had in mind. —Dom Sinacola