If you grew up watching movies in the mid-to-late-’90s, you inevitably had a favorite Adam Sandler movie. Few actors have become comedic superstars the way Sandler did in his heyday. While the broad physical comedy of Jim Carrey began to wane into the new millennium, Sandler’s star status has continued to grow – he’s simultaneously one of the world’s most popular and contentious performers. From the immature, anger-prone protagonists of his early efforts like “Billy Madison” and “Happy Gilmore” to the genial-schlub leading men of “50 First Dates” and “Grown Ups,” Sandler’s persona has endured through every transition in the comedy world of the last 25 years.
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What is it about Adam Sandler that stands the test of time? Most critics use him as a punching bag, writing off even his most enjoyable movies, essentially turning him into the poster boy for cash-grab, brain-dead comedies. Even when he reminds us of what a fantastic dramatic actor he can be by working with heavyweight auteurs like Paul Thomas Anderson, Noah Baumbach, and, most recently, The Safdie Brothers, people act like it’s a shock that the real Sandler is more than just fart jokes and silly voices. After all, audiences far and wide still love the Sandman – even for his less-than-great Netflix outings (“The Do-Over,” anyone?)
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Sandler is not only one of our most reliable and unusual leading men: he’s also a great character actor and a legend in the comedy landscape. With this week’s anticipated release of the Safdie’s electrifying new film “Uncut Gems,” it feels like the perfect time to look back at the decade-spanning career of not only one of our most vital, influential comedic voices, but one of our most underrated actors, period. – Max Roux
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“Billy Madison” (1995, Tamra Davis)
“Billy Madison” was sort of the genesis for what would become the Sandler archetype: angry, unhinged, but ultimately loveable man-child who succeeds against all odds. In retrospect, “Billy Madison” is insanely dark. It’s essentially an underdog story about a deranged grown man who uses his family’s wealth to go back to school in order to prove he can successfully run his father’s multi-million dollar business. In today’s market-tested-to-death studio system, it’s hard to imagine a film this absurd getting bankrolled. Tamra Davis clearly had an understanding of Sandler’s gifts and played to them beautifully, evoking the kind of absurdist spirit of the Marx Brothers or the Zucker Brothers in their heyday. “Billy Madison” honest-to-God feels like Sandler’s lowbrow approach to a Luis Bunuel film. It’s that fucking bonkers. What’s always been present in Sandler’s work is his humanity, and that’s what makes his characters so relatable and deeply likable. Effortlessly watchable and charismatic, his performance in “Billy Madison” is truly underappreciated for how well he can balance the physical and emotional demands of playing a combustible combination of deep-seated male rage and insecurities, all under the guise of a broadly funny goofball. – Max Roux
“Happy Gilmore” (1996, Dennis Dugan)
Anyone who’s not very good at golf but tried to play a round anyway can tell you that it can be an intensely frustrating, even infuriating experience. It can make you want to pound your club into the grass, or throw it into a nearby body of water, or even clobber Bob Barker if he just so happens to be standing nearby. The brilliance of “Happy Gilmore” is that it encapsulates the impotent fury of a crappy golf game better than just about any other mainstream comedy we can think of, “Caddyshack” included. Indeed, Happy (Sandler) is not a good golfer. He’s not even really a good person. He’s a hockey goon with a hair-trigger temper whose only redeeming quality is that he dearly loves his sweet grandma and wants to keep her out of a terrible retirement home run by a sinister, mustachioed orderly (played an uncredited Ben Stiller). For all the film’s endearing, albeit sophomoric humor and grade-school silliness, there’s a real, palpable anger in Sandler’s performance here: it’s there in the scene where he starts screaming at a golf ball can’t make contact with, or in another sequence where he breaks a beer bottle in half and starts brandishing at his smug rival, Shooter McGavin (Christopher McDonald). Bearing witness to these loopy moments, you can see why Paul Thomas Anderson wanted to cast Sandler as desperation-choked loner Barry Egan in “Punch-Drunk Love” (this and “The Waterboy” are Sandler’s unofficial Angry Sports Movies). Of course, “Happy Gilmore” is also possessed by the lunatic weirdness of early Sandler gems like “Billy Madison”: Dennis Dugan’s movie is aggressively absurd, instead of pandering and lazy in the way that “Jack and Jill” and the “Grown Ups” movies are content to be. If nothing else, “Happy Gilmore” contains a scene where Sandler’s fuming hooligan pries a golf ball from the iron jaws of a, particularly nasty alligator. What else do you need to know? – Nicholas Laskin
“The Wedding Singer” (1998, Frank Coraci)
Even those who don’t tend to go for Sandler’s broad early comedies can agree that “The Wedding Singer” is one of the better ones. Frank Coraci’s rom-com is both totally charming and unaffectedly sincere and good-hearted: a winning trifle that employs its star’s signature penchant for gross-out humor in the right (which is to say, measured) doses, and mostly relies on the considerable chemistry between Sandler and co-star Drew Barrymore to carry it through its more conventional passages. Sandler plays Robbie Hart: a curl-sporting singer-for-hire who falls into a deep depression after his girlfriend stands him up on their wedding day. Naturally, this leads to a lot of inimitable Sandman meltdowns, including a scene where our hero belts out the lyrics to a furiously bitter ballad titled “Love Stinks” before suffering an on-stage temper tantrum (a later number, titled “Somebody Kill Me,” is as darkly funny as anything in Sandler’s early filmography). As always, Sandler makes time for his pals in glorified cameo roles: this time, it’s Happy Madison stalwart Allen Covert as Robbie’s horny pal, Steve Buscemi as a sozzled maniac who gives what might be the worst wedding toast in movie history, and Jon Lovitz, who mostly just shows up to sing “Ladies Night” and be creepy. However, Sandler has always had a gift for playing nicely alongside certain female co-stars (Jennifer Aniston is another example, in spite of the fact that the two movies they’ve starred in together are pretty terrible). In that regard, Barrymore is still the actor’s most ideal match. Sandler’s big-screen persona could be described as an adult version of the kid who made you giggle at dirty jokes in Hebrew school class, and there’s something sweetly innocent about his scenes with Barrymore that makes “The Wedding Singer” one of the Sandman’s most pleasant and rewatchable comedies. – NL