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
“Big Daddy”
You might be hard-pressed to find many critics who were willing to call Sandler’s 1999 blockbuster “Big Daddy” a step in a more mature direction, but in hindsight, it was the first sign of more emotionally mature work from the Sandman. Sure, there were plenty of the usual broad jokes (Leslie Mann’s character’s arc is pretty much defined by her one-time employment at Hooters), but the underlying emotional arc of Sandler’s bachelor Sonny Koufax is one that felt like Sandler coming to terms with his own maturation into his 30s. And yes, it’s another Sandler film that, with a few tweaks to the logline, could be considered a disturbing drama: emotionally stunted 30-something poses as his more successful, mature friend and claims custody of a 5-year-old boy who shows up on his doorstep. But that’s sort of the magic of Sandler, especially in the first stage of his career. He’s able to take otherwise insane plots and unlikeable protagonists and bring warmth to them, making them accessible to young audiences, while still giving older fans some darker jokes to enjoy. “Big Daddy” has all the hallmarks of classic Sandler – the strangely relatable meltdown he has in a McDonald’s when he discovers they stopped serving breakfast earlier than he was led to believe, or breaking into an exceptionally unfestive prick’s house on Halloween when he denies the 5-year-old adoptee candy – but the last act, in particular, showcased some of Sandler’s hidden gifts for drama. His courtroom plea for acceptance from his cold, unloving father felt oddly cathartic for a Sandler film, once again proving that, beneath the juvenile veneer, there was a fascinating character actor waiting to be unleashed. – MR
“Punch-Drunk Love” (2002, Paul Thomas Anderson)
What separates Paul Thomas Anderson from many of his fellow auteur directors is that he openly goes to bat for actors and films that are often considered “guilty pleasures.” He’s an unabashed fan of Tom Cruise (who is hands down one of our finest actors and movie stars) and most notably, the ’90s comedies that made Sandler a star. Following up on his 1999 magnum opus “Magnolia” with a love story starring the unimaginable pairing of Sandler and Emily Watson, PTA introduced the world to what would be known as “dramatic Sandler.” As Barry Egan, the lonely plunger salesman who discovers a marketing error in a Healthy Choice airline miles give-away that sees him stocking up on pudding in order to retrieve infinite travel miles, Sandler is quite simply a revelation. Much in the same way Anderson broke down the archetypal Cruise persona in “Magnolia,” the director augmented the kind of rage-prone protagonists Sandler was known for playing, and married it with his own deep-seated insecurities. The result was a character that honed in on the most human and recognizable qualities of Sandler’s past characters, giving us a rare glimpse at the underlying sadness of Sandler, the thespian. There might not be a more painfully realistic portrayal of social anxiety than the sequence when Barry goes to one of his seven sisters’ birthday party, which begins with his sisters antagonistically ganging up on him, calling him “gay boy,” and ends with him taking a hammer to their sliding glass door. It ends up being some of the most emotionally affecting work that Sandler has ever done. The way he jolts slightly upon being snuck up on, or stumbles over his nephews’ toys, or awkwardly tells his brother-in-law “business is very food,” is all in service of an incredibly detailed portrayal of trauma-induced anxiety. Barry Egan is the result of a brilliant director mining the psychological depths of a comedic superstar’s persona, giving us Sandler’s most nuanced and deeply felt performance to date. – MR
“Spanglish” (2004, James L. Brooks)
There are a few different categories of James L. Brooks movies, and his 2004 dramedy “Spanglish” ultimately falls somewhere in the middle of the spectrum. It’s a middling, baggy, occasionally quite moving familial drama where contrived scenes stand right next to moments of real power and insight. In other words, it’s no “Terms of Endearment,” but it also certainly isn’t “How Do You Know.” And yet, “Spanglish” contains yet another revelatory dramatic performance from Sandler, this one hot on the heels of his career-redefining turn in “Punch-Drunk Love.” Brooks was allegedly inspired to cast the onetime Waterboy after seeing his brilliant, emotionally exposed turn in Paul Thomas Anderson’s hallucinatory love story, and while Sandler’s work in “Spanglish” is less explosive – and, ultimately, less memorable – than that earlier film, his work for Brooks offered further proof that the Sandman possessed the chops necessary to deliver a credible dramatic performance in an auteur-helmed prestige project. Here, Sandler plays John Clasky: an easygoing chef and committed family man whose amicable, schlubby surface demeanor disguises a roiling sea of insecurity and inadequacy. The scene where John’s wife Deborah (Téa Leoni, excellent) confesses her infidelity to her visibly crushed husband showcases some of the most delicate screen acting that Sandler has ever done – in fact, the entire movie is worth watching for this scene alone. Sandler is also convincingly manic in the scenes where he’s cooking gourmet food under a considerable degree of pressure, and similarly persuasive in his more serene and suggestive domestic scenes with Flor (Paz Vega), who plays the family’s housekeeper. Brooks’ screenplay sometimes feels worked-over and the film’s insights into upper-middle-class malaise are not quite as cutting as they should be, but if nothing else, “Spanglish” offers a kind of connective thread for those who were wondering how the great Cloris Leachman ended up in Sandler’s football yukfest “The Longest Yard.” – NL
“You Don’t Mess With The Zohan” (2008, Dennis Dugan)
Sometimes, a man just gets tired of all the aggression, the warring, the blood on his hands and the lives lost in the cycles of endless perpetuating violence. Written by Judd Apatow, Robert Smigel (Triumph The Insult Dog) and Sandler himself (not a rare occurrence, but not a super frequent one either), “You Don’t Mess With The Zohan,” is this American Jewish comedy trios’ attempt to tackle the Israeli/Palestinian conflict with humor and as you’d expect, the results are mixed, but it’s also one of the more inspired and hilarious Happy Madison Productions of this century (there’s not many of them) Sandler plays Zohan Dvir, a misunderstood elite Israeli counter-terrorist who yearns to fulfill more meaningful dreams. Sick of the bloodshed, shamed by his parents for harboring secret hairdressing dreams, Zohan fakes his death and moves to American to realize his desire to be a hairstylist for Paul Mitchell. It’s silly as hell, stereotypical, sometimes problematic and admittedly, painfully juvenile at times. But when it works, oh boy, it works, and one suspects the inclusion of Apatow and Smigel make this one kind of salvageable/kind of amazingly hysterical at times. Featuring incredible supporting turns by John Turturro (as a Palestinian terrorist named Phantom), Emmanuelle Chriqui, Nick Swardson, Ido Mosseri, and Lainie Kazan as the mom Zohan loves to “make sticky with,” ‘Zohan’ is very wrong at times. But Sandler is just so damn good at playing his interpretation of a very Israeli soldier with a sensitive side— super confident, somewhat thoughtful, despite being an arrogant, clueless womanizer and an elite killer to boot. ‘Zohan’ is absurdist, sometimes stupid, and yes, cringe-worthy at times, but it’s dumb gags about Israeli disco-pop, hummus, Israeli soft drink Fizzly Bubbly, and, Zohan’s outrageous libido and cocksmanship make for a film some of us love more than we may want to admit. – Rodrigo Perez
“Funny People”
After the success of “The 40-Year Old Virgin” and “Knocked Up,” veteran comedy writer/director Judd Apatow was in the coveted position of being able to do whatever he wanted next. At the time, it made sense that he would want to cash in that blank check with something more personal and in 2009, he did just that thing with“Funny People.” On paper, it sounded like another hit with crossover potential for awards recognition. Veteran comedy superstar Sandler teaming up with new-school stars like Seth Rogen and Jonah Hill to make a dramedy in the vein of vintage James L. Brooks. But add in the fact that Sandler’s George Simmons – a clear stand-in for the real-life Sandler – is a morose, jaded comedian who gets diagnosed with cancer, and spends the last 45 minutes of the film with Apatow’s real-life family at their beautiful home in Marin County, and you see why “Funny People” ended up being the box office disappointment it was. So yes, Apatow’s self-reflective ode to the world he loves was undeniably baggy and flawed, but it had glimmers of what could have been the best film of his career, and most importantly, it provided Sandler with his best dramatic role since “Punch-Drunk Love.” If Paul Thomas Anderson gave us the first real dissection of the on-screen Sandler persona, then Apatow gave us the most raw dissection of the man himself. There’s no way to not associate this role with the real-life Sandler cashing in on lazy studio projects and the scarily similar studio comedies Simmons mounts his success on. The film offers Sandler a chance to reckon with his own career trajectory, as well as the potentially alienating, flawed aspects of his own personality. “Funny People” is most successful when it allows Simmons to be unlikeable, and Sandler is always up for the challenge. He embraces every aspect of the challenging role, offering one of his most vulnerable and unapologetic performances yet. – MR
“Men, Women & Children” (2014, Jason Reitman)
Let’s get this out of the way immediately: Jason Reitman’s “Men, Women & Children” is not a good movie. It’s essentially “Reefer Madness” for the era of online over-saturation: an unexpectedly shrill alarmist dud from the otherwise perceptive filmmaker who gave us humanist jewels like “Thank You For Smoking” and “Young Adult.” And yet, if “Men, Women & Children” can be said to possess one overriding redeeming factor, it’s Adam Sandler’s quiet, observant, and ultimately devastating supporting performance as Don Truby: a despondent sad sack trapped in a frigid, loveless marriage with his equally unsatisfied wife Helen (Rosemarie Dewitt, bless her heart). At a certain point, it can seem like literally every character in “Men, Women & Children” is addicted to online pornography, but Sandler is the only member of the cast who manages to authentically sell his character’s ethically compromised relationship to tech. It’s not nubile flesh and cheap, lurid thrills that this perpetually depressed middle-aged dad is after: like Barry Egan in “Punch-Drunk Love,” Don is simply looking for some kind of human connection, however, he can get it. He’s just more prone to moping and less prone to punching out sliding glass doors. This leads to a mind-boggling plot development where both the Trubys begin to use Ashley Madison as a means for engaging in extramarital affairs, although Sandler is so good in the scene where he tracks his wife to a bar where she’s meeting her new suitor that he almost makes you forget how contrived the scene’s basic setup is. If nothing else, “Men, Women & Children” proves that not all “serious” Adam Sandler movies are created equal – and that, in spite of how low Reitman’s film goes (and it does go low), Sandler never allows himself to sink into the muck. – NL
“The Meyerowitz Stories: New and Selected” (2017, Noah Baumbach)
Watching Adam Sandler absolutely lose his shit over his inability to find a decent parking spot on a residential street in New York City has got to be one of the more relatable moments in Noah Baumbach’s oeuvre. Quick show of hands: who’s been there? What’s so brilliant and heartbreaking about Sandler’s turn in “The Meyerowitz Stories: New and Selected” is how it embraces the more recognizable characteristics of Sandler’s comic iconography (his frightening, furious outbursts, his hangdog line readings, his talent for goofy sing-a-longs) along with the more soulful side of the actor that we only occasionally get a full glimpse of. Sandler plays Danny Meyerowitz: the depressed, recently-divorced oldest child of the dysfunctional Meyerowitz clan. Sandler is the least accomplished of the Meyerowitz siblings, the others being his glum sister Jean (Elizabeth Marvel) and the aggressively type-A Matthew (a tightly-wound Ben Stiller), with whom he has a complicated relationship. Like all of Baumbach’s films, “The Meyerowitz Stories” is marvelously acted all around, but it’s arguably Sandler who all but walks away with the movie. Watching him fret over the prospect of sending his aspiring filmmaker daughter to college, or a scene late in the film where he must come to terms with the prospect of his thoroughly difficult father’s lingering mortality, is enough to bring a tear to your eye (the set-piece in which Sandler and Stiller break into a cringingly awkward middle school-level fight on the lawn of a college campus is the rare moment that will unite fans of both “The Squid and the Whale” and “Happy Gilmore”). Ultimately, Sandler acclimates himself so deftly to Baumbach’s preferred ecosystem of neurotic New York Jews that we can only hope that the two work again at some point in the future. – NL
“Uncut Gems” (2019, Josh & Benny Safdie)
In films like “Punch-Drunk Love” and “The Meyerowitz Stories: New and Selected,” directors Paul Thomas Anderson and Noah Baumbach managed to harness the power of Adam Sandler’s oft-remarked-upon sense of sadness. These films weren’t reinventions of the Sandler persona – just nuanced and sympathetic interrogations of it. Sandler isn’t leaning on the weight of any of his past performances in “Uncut Gems”: this performance is much of a reinvention as anything we’ve seen from any actor, ever. Of course, it helps that Howard Ratner – a loose cannon Diamond District jeweler beset by heedless aspirations and a series of escalating debts, a schmuck with a knack for self-preservation who is hopelessly addicted to sewing the seeds of his own destruction – is being played by an actor who knows how to make fine use of a volcanic temperament. With “Good Time,” Josh and Benny Safdie staked their claim as directors who take recognizable marquee movie stars and plunge them headfirst into their ruthlessly frenetic and thoroughly streetwise world. The brothers make use of Sandler’s gifts in a similar fashion to what they accomplished with “Good Time” star Robert Pattinson: in both cases, the brothers successfully weaponize familiar elements of their respective lead’s public identities. Sandler’s Howard Ratner is, among other things, greedy, maniacally focused, romantically unfaithful, and prone to both spectacularly ill-conceived schemes and also embarrassing exhibitions of childish rage. Howard is also a man with a dream, and Sandler’s ability to ground even this unremitting caper’s most unhinged plot developments (just wait until you see how he ends up bound and butt-naked in the trunk of a Mercedes) in something emotionally real is astonishing. There is also something poignant about the act of casting one of the world’s most recognizable Jewish movie stars in a film that manages to brilliantly catechize many of the inherent paradoxes and cultural particulars of modern Judaism through the prism of the crime genre. Sandman: this is how you win. – NL
Honorable Mention
To this day, the purest and most uncut (if you’ll forgive us the Safdie-related pun) distillation of Sandler’s comedic ethos can be found in his first two comedy LPS. “They’re All Gonna Laugh At You” and “What The Hell Happened To Me?” summon the nostalgic, aggressively R-rated aura of juvenile middle-school hilarity, hearkening back to a time when you and your friends would stay up all night binging comedy albums and try to brainstorm the funniest and filthiest jokes. To those who value civility and good taste in their comedy, look elsewhere. To those who want to hear Sandler impersonate hateful New England toll booth attendants, foul-mouthed goats, shrill Jewish mothers, someone named “Fatty McGee,” and an early version of “The Waterboy’s” Bobby Boucher, these albums are a veritable treasure trove.
As far as the rest of Sandler’s cinematic body of work is concerned: “Airheads” is a solid ’90s crudball comedy, and Sandler gives the film’s most appealing performance as the pea-brained drummer of a Sunset Strip metal band who is an inexplicable babe magnet. The Sandman also does his “Midnight Run” thing in the Ernest Dickerson-directed buddy comedy “Bulletproof,” where he makes a fine, fast-talking foil for his more cool-headed co-star Damon Wayans.
Sandler reunited with Drew Barrymore for the adorable rom-com “50 First Dates,” which is one of the better mid-period Happy Madison vehicles in spite of the questionable nature of its plot and a few pointlessly tasteless gags. While it’s very hard to defend the slapdash laffer “Little Nicky” as an empirically good movie, Sandler’s bizarre, mush-mouthed performance as the slacker son of Satan is… well, it’s nothing if not committed.
Sandler mined the darker, more dramatic side of his screen persona once more in the Mike Binder-directed male-bonding weepie “Reign Over Me,” giving a performance that, to this day, divides fans of both Happy Madison and his arthouse work.
The Sandler-starring “The Cobbler” is unquestionably the worst movie Tom McCarthy (“Spotlight,” “Win-Win”) has ever directed: an appalling, rancid fantasy that traffics in more racism, stereotypes, and narrative tropes than “That’s My Boy.” That said, Sandler is fairly good in the film – he’s doing the best he can given the material he’s working with. Sandler also pops up in a memorable cameo in his pal Chris Rock’s “Top Five,” where he evinces more zeal and genuine screen presence in less than five minutes than he does throughout the entirety of “Bedtime Stories” or “The Ridiculous 6.”
“Uncut Gems” is in select theaters now. Trust us, you won’t want to miss it. – Nicholas Laskin