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Adam Sandler’s Movies, Ranked Worst to Best

From ‘Happy Gilmore’ to ‘Uncut Gems,’ the greatest (and most grating) films of the star we call the Sandman

Adam Sandler in various film roles

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He goes by many names: Billy Madison, Happy Gilmore, Zohan Dvir, Canteen Boy, Opera Man, the Sandman. But ever since the mid-1990s, Adam Richard Sandler has put his God-given moniker above the title of his movies and established himself as one of the major screen comedians of the past 30 years. You may love his angry, abbie-doobie man-children and every-guy heroes, and consider him a comic genius. You might think most of his work is juvenile and ridiculous. You could even make a case for his lack of an Oscar nomination for his role in Uncut Gems qualifying as a prosecutable crime [raises hand]. Regardless, Sandler’s ability to go from standout Saturday Night Live weirdo to human hit factory whose Happy Madison production company netted a multimillion-dollar deal with Netflix has established him as a reliable, consistently bankable superstar.

In honor of fans finally — finally! — getting the long-awaited Happy Gilmore 2, we’ve ranked all of Adam Sandler’s movies to date. Well, most of his movies: We’ve left out the ones in which the Sandman shows up for what’s basically a credited (or uncredited) cameo, so no Coneheads and none of the movies where he lends his mug to a fellow famous actor’s project for a single scene. Ditto the animated movies that just use Sandler’s voice, with one very notable exception. From Billy Madison to Punch-Drunk Love, here are our picks for the best and the worst of the cinema dú Sandman.

8

‘The Meyerwitz Stories (New and Selected)’ (2017)

Sandler’s character in writer-director Noah Baumbach’s brilliant dramedy about a family of artists is the first of the adult Meyerwitz offspring we meet — he’s Danny, a recently unemployed guy with a college-age daughter, a bum foot, a nice singing voice (especially when it comes to crooning Lisa Lisa and Cult Jam’s hit “Head to Toe”), and major father issues. And though the Sandman is part of an ensemble that includes Ben Stiller (playing his brother), Dustin Hoffman, Adam Driver, Elizabeth Marvel, Judd Hirsch and a truly daffy Emma Thompson, he’s the real key to Baumbach’s look at how the ties that bind can also suffocate you to death. This is truly one of the hidden gems in Sandler’s back catalog, tapping into his facility for physical comedy, his often underutilized acting chops, and his ability to go from zero to “Shut the fuck up!!!” rage in an instant. —D.F.

7

’50 First Dates’ (2004)

Given the chemistry they showed in The Wedding Singer, it’s a wonder it took six years for Sandler and Drew Barrymore to reunite in this sweet ice cream sundae of a rom-com. Sandler plays Henry Roth, a womanizing marine-park veterinarian in Hawaii. Barrymore is Lucy, a local art teacher who lost her short-term memory in a car accident and has been reliving the same day ever since. When they meet-cute at the diner where she goes for breakfast each morning, it’s love at first sight for Henry. But he has to find a way to re-meet, and re-charm, Lucy every 24 hours. There’s a signature Sandler guitar song, Rob Schneider playing a goofy, racially insensitive caricature, and a walrus named Jocko as an adorable second banana. What more could you ask for in exchange for 90 minutes of your time? —M.F.

6

‘The Waterboy’ (1998)

In Adam Sander’s breakthrough movies (Billy Madison, Happy Gilmore, The Wedding Singer), he plays zany, over-the-top goofballs living in relatively staid, recognizable worlds. He flipped the formula around in this 1998 comedy, where he plays a dim a dim, soft-spoken, football team waterboy in a twisted, cartoon version of Louisiana, where barbecued anaconda snakes are served for dinner and nobody flinches when a college professor looks exactly like Colonel Sanders. Sandler’s character becomes a star football player after discovering very unlikely running and tackling skills, but he has to hide his success from his religious mother, played by Kathy Bates. Critics loathed it (“[Sandler] creates a character whose manner and voice has the effect of fingernails on a blackboard,” wrote Roger Ebert in a scathing, one-star review). But there’s a reason that it’s become a cult classic that plays in constant rotation on basic cable. —A.G.

5

‘The Wedding Singer’ (1998)

This was a turning point for Sandler, an Eighties-themed romance that established him as a bona fide heartthrob, as he jumped into the Nineties’ obsession with the Hair Decade. His New Jersey wedding singer Robbie Hart is at the top of his game in 1985, crooning the hits from “True” to “You Spin Me Round (Like a Record).” Then he gets jilted at the altar, making him change his tune to “Love Stinks.” Can Robbie find true love with waitress Drew Barrymore? Maybe — with a little help from Billy Idol, who really deserved a Best Supporting Actor nomination for his star turn. The Wedding Singer lives up to the spirit of the music, as Sander’s gawky New Wave joie de vivre goes up against the angsty, no-fun Nineties, symbolized by Steve Buscemi as a cranky wedding guest. But it holds up as one of the era’s most evergreen rom-coms, thanks to Adam and Drew. You KNOW this much is true. —R.S.

4

‘Punch Drunk Love’ (2002)

When he was starting out, Paul Thomas Anderson demonstrated a genius for giving established stars uncharacteristic roles that surprised their fans. (Think Burt Reynolds in Boogie Nights or Tom Cruise in Magnolia.) But his masterstroke was suspecting that Sandler would be perfect to play Barry, a mentally troubled lonely guy in love; he’d providing the comic dynamo with an opportunity to access his untapped capacity for nuance. As the anxious Barry courts Emily Watson’s shy, sweet Lena, Sandler may evoke the raging man-children he’d portrayed in hits like Happy Gilmore, but never before had he allowed himself to be so vulnerable, daringly excavating real pain underneath the manic slapstick. At the time, Punch-Drunk Love seemed like a revelation. Now, it’s rightly regarded as merely the first of many brilliant, layered dramatic performances Sandler had in store. —T.G.

3

‘Uncut Gems’ (2019)

Longtime chroniclers of New York’s seedy underbelly and its shadier denizens, filmmakers/siblings Josh and Benny Safdie reached their apex by teaming up with Adam Sandler, who’s electrifying as Howard Ratner, a low-life jeweler and inveterate gambler on a losing streak trying to outrun the loan sharks who want their money. They somehow find room in this extraordinarily tense thriller for both pop star the Weeknd and Boston Celtics great Kevin Garnett, each playing ingeniously malicious versions of themselves. But Uncut Gems is turbo-charged by Sandler’s bravura performance, which encapsulates the fleeting euphoria and flop-sweat desperation of an addict chasing the rush of the seemingly perfect parlay. Howard drowns in front of our eyes, his fast-talking no match for the tidal wave about to crash on top of him. —T.G.

2

‘Happy Gilmore’ (1996)

There’s only one true debate among Sandlerphiles: whether this movie, about a hockey bruiser who becomes a PGA Tour golfer in a get-rich-quick scheme to buy his grandma’s house back, or Billy Madison is his best. The fact that Happy Gilmore birthed a sequel, which reprises not just the story line of Happy being a cash-strapped burnout but iconic characters — from Christopher McDonald’s tormented pro Shooter McGavin to Julie Bowen’s happy-place fantasy girl Virginia and Ben Stiller’s mustachioed villain Hal — surely gives it an edge, for some. The original was savaged by critics (this despite including a fist fight with Bob Barker!) but cemented the Sandler playbook: a sweet and slightly hotheaded idiot rises above his own failings to triumph over mean, pretentious douchebags. It’s a cinematic masterpiece that said, “You’re in Sandman’s world now, grandma!” —M.F.

1

‘Billy Madison’ (1995)

Before the cinema du Adam Sandler mostly meant bro-baiting, an excuse to showcase friends and family on the big screen, and Netflix-sponsored, phone-it-in paydays, the ex-SNL star gave us this genuinely weird, warped story of a spoiled rich doofus who, in order to stay spoiled and rich, must do the impossible: repeat kindergarten through high school in record time. It remains a masterclass in manchild comedy with Sandler in all his unhinged abbie-doobie glory, fighting off 10-foot-tall penguins and staging elaborate musical numbers that end with operatic pleas for gum. To merely hear someone say “Stop looking at me, swan!” or “That Veronica Vaughn is one piece of ace” or any of the dozens of other beautifully absurd lines is to instantly break into a fit of collective giggles. Not to mention that it features the greatest academic competition to ever end with the words, “I award you no points, and may God have mercy on your soul.” The Sandman had a whole career’s worth of misfits, lunkheads, everydudes and everydads ahead of him when he made this early star vehicle. But he’d never be this simultaneously over-the-top odd and out-and-out hilarious again. —D.F.