From high comedy to low, there’s more variety than you think in the actor’s filmography.
Advertisement

No actor has been harder to pin down in his post-Saturday Night Live career than Adam Sandler. After breaking out by transferring his SNL work (described, not without admiration, by former SNL colleague Bob Odenkirk as "kind of dicking around") to the big screen, Sandler went on to not only found a hugely successful production empire for himself and his comic pals, but also turn in compellingly complex performances in films from major directors. 

The temptation is to undervalue Sandler's self-produced comedies while holding aloft Sandler films made by "real" directors. The reality is, like Sandler, more complex however, as auteurs from Paul Thomas Anderson to the Safdie Brothers to Noah Baumbach and James L. Brooks all saw the comic and dramatic potential in Sandler's stunted manchild schtick.

So, without further ado, here's our list of the 10 best Adam Sandler movies to watch for a full sense of his unique talents.

Best Adam Sandler Movies BILLY MADISON, Austin Pool, Adam Sandler,
Credit: Everett Collection

10. Billy Madison (1995)

Sandler's first proper post-SNL success set the character template he and others would mine, with greater or lesser success, for the next three decades. In Billy Madison, Sandler plays the titular spoiled and childish (or childlike, if you're generous) hotel heir whose anticipated elevation to head of his father's company becomes contingent upon him going back to school. Specifically, upon finding out that his father's wealth and power allowed the now-grown Billy to skate by unearned, Sandler's shenanigans-prone character must repeat—and pass—grades K-12 in six weeks.

As setups go, it's a fine vehicle for the immature  Billy to (often with comical roughness) interact with actual children, and for Sandler to sow the seeds of the evolving but similar character arcs to come. An Adam Sandler character is usually , if belatedly, all about growing up — and changing for the better. Even if, as with Billy's journey, that process comes yoked with streaks of hair-trigger hostility and self-doubt. Along with its vein of absurdist and juvenile humor, there's a core of sweetness and dawning decency that will mark much of the Adam Sandler canon. 

Available to buy on: Amazon

You'll also love: Arthur (1980). Dudley Moore plays a libertine heir to a massive fortune who must follow his father's orders in order to inherit the cash. Sounds familiar, although Moore's Arthur is less a slobbish manchild than a drunken but good-hearted British wastrel, and his task involves a loveless marriage to cement a business deal. Still, fans of talented comic actors begrudgingly growing up a little will find common ground.

Best Adam Sandler Movies
Credit: Bob Marshak/Columbia Pictures

9. Spanglish (2004)

Sandler's beleaguered husband in James L. Brooks's uneven family dramedy Spanglish often looks like an early Adam Sandler protagonist playing dress-up as an adult. A successful and talented chef, Sandler's John Clasky, in his rumpled clothes and conflict-averse mumble, navigates his troubled marriage to Téa Leoni (sourly written as the stereotypical rich shrew) and his growing relationship with the family's new Mexican maid (Paz Vega) and her teenage daughter in a culture clash comedy from the acclaimed writer-director of Broadcast News and As Good As It Gets

The split between a Sandler movie (as represented by those made by Sandler's Happy Madison Productions) and outside films by big name directors is a deceptive one. Here, Brooks casts Sandler because of his Happy Madison persona, as John's increasingly desperate attempts to hold his family together are imbued feelingly with the actor's perpetual, overmatched arrested adolescence. Brooks's script is overwritten and conspicuously clever, with Sandler affectingly channeling the filmmaker's many speeches through his signature sentimental silliness to eye-opening effect. As we'll see later on this list, Sandler's work with name directors invites accusations of underachieving in his own, often underwhelming Happy Madison films. Spanglish is just one example of a good director seizing on, and expertly deploying, the strengths Sandler routinely shows there. 

Available on: Starz

You'll also love: Down and Out in Beverly Hills (1986). Culture clash among the rich gets a raucous and insightful airing in Paul Mazursky's comedy. Rich and unhappy Richard Dreyfuss and Bette Midler take in a homeless but cultured Nick Nolte, and everything from their marriage, to their relationship with their grown kids and their exploited Mexican maid, are all thrown into chaos. 

Best Adam Sandler Movies
Credit: Tracy Bennett/Columbia Pictures

8. You Don't Mess With the Zohan (2008)

Written by Sandler, Smigel, and Judd Apatow, this knockabout action comedy's politics may not have aged all that well. (Planned before 9/11, the long-delayed film still traffics in regrettable Arab terrorist stereotypes played by the likes of John Turturro and Rob Schneider.) But You Don't Mess With the Zohan features one of Sandler's most confidently atypical performances. Getting himself into action-hero shape to play the effortlessly deadly Mossad officer-turned-high-fashion hairstylist of the title, Sandler creates a slapstick Israeli superhero that sees him abandon his usual bag of schlubby comic tricks for an effortlessly silly and sexy portrait of absurdist badassery. 

Whether battling waves of assassins (catching bullets in his nostril or dealing street corner justice with improbably quick and nimble feet) or happily servicing his elderly, eternally smitten salon clientele, this is Sandler at his most relaxed and amusingly authoritative. While there's always plenty of physical comedy in a Happy Madison joint, here, Sandler is the delightfully serene center of the gag-storm, which only makes you wish he'd gone outside his usual stable of workmanlike directors (here Dennis Dugan) to truly choreograph the comic action. 

Available to buy on: Amazon

You'll also love: OSS 117: Cairo Nest of Spies (2006). Future Best Actor winner Jean Dujardin and The Artist director Michel Hazanavicius first teamed for this loopy French satire of 1960's-era James Bond. Dujardin is a Peter Sellers-worthy marvel as the preening, often accidentally heroic Hubert Bonisseur de La Bath (alias OSS 117), channeling early Sean Connery with a knowing/clueless smirk.

Best Adam Sandler Movies
Credit: Tracy Bennett/Universal

7. Funny People (2009)

Sandler allowed lifelong friend Apatow to craft this tale (of a successful star of lowbrow comedies facing a grave illness) around him. The bankable lead in such critically lambasted comedies as MerMan and Astro-Not, Sandler's George Simmons is a canny analogue of Sandler himself. The ailing Simmons's post-diagnosis journey of personal and professional discovery takes digs both at Sandler's Happy Madison output and the public perception of Sandler as coasting on concept comedies and silly voices. 

Teaming with Seth Rogen (himself a sly deconstructor of audience expectations) as the young comic hired on as the lonely George's companion and writer as the movie star goes back to his stand-up roots, Sandler creates a rueful portrait of the isolated, talent-betraying star the actual (universally well-liked and apparently stable) Sandler might have become. Despite a third-act attempt by George to reconnect with the woman who got away (Apatow's wife Leslie Mann), Funny People allows Sandler to portray one of the least sympathetic and most layered iterations of his signature persona. Apatow rounds out Sandler's usual themes by suggesting that growing up late doesn't always mean getting everything you want.

Available to buy on: Amazon

You'll also love: My Favorite Year (1982). Before Perfect Strangers, Mark Linn-Baker perfected his exasperated double-takes as worshipful sidekick to alcoholic movie idol Peter O'Toole in this comedy set in the golden age of television. Booked to revive his waning career (and dodge the taxman) on a Your Show of Shows-style live sketch show, O'Toole's Alan Swann does his dapper, drunken best to ditch his designated minder, with the ailing star and the Brooklyn schnook affectingly bonding along the way. 

HAPPY GILMORE, Bob Barker, Adam Sandler, 1996, (c) Universal/courtesy Everett Collection
Credit: Everett Collection

6. Happy Gilmore (1996)

Anger is at the core of this knockabout take on the sports movie, with Sandler's titular would-be hockey star turning to golf to make bankable use of his undeniable skills in beating the bejesus out of things with a stick. Happy Gilmore is another of Sandler's emotionally stunted Gen-X underdog heroes, his thwarted dreams and gnawing self-doubts seeing him alternate between sappy sentiment (his golf quest is spurred by his love for his broke and beloved grandmother), and a seething, "You think you're better than me?" inadequacy that endangers both his plan and anybody who remotely crosses him. 

Only slightly less reliant on anything-for-a-laugh gags than 1995's Billy Madison (there's still room for a cursed alligator and a fistfight with game show host Bob Barker), Happy Gilmore introduces shades of the sweetness warring with the typical Sandler character's boorish clowning. As satisfying as it is for Happy to one-up sneering golf nemesis Shooter McGavin (Christopher McDonald, creating an all-time comic villain), we still root for Sandler's unstable but lovestruck goofball to win over love interest Julie Bowen by engineering an ice rink doubles' skate to "Endless Love."

Available to buy on: Amazon 

You'll also love: Slap Shot (1977). Speaking of brutish athletes who love to bash things, this ramshackle depiction of the disreputable world of minor league hockey stars Paul Newman (in one of his most relaxed and funny performances) as the player-coach of the basement-dwelling Charlestown Chiefs. If ever a team had a spot for Happy Gilmore, it's the Chiefs. 

THE MEYEROWITZ STORIES Dustin Hoffman and Adam Sandler
Credit: Atsushi Nishijima/Netflix

5. The Meyerowitz Stories (New and Selected) (2017)

Noah Baumbach, like Brooks and Apatow, made expert use of both Sandler's public and onscreen persona, casting him as Danny Meyerowitz, the ever-slighted son of pompous artist Dustin Hoffman. Danny, the downtrodden, soon-to-be divorced father of a cherished, college-bound daughter, is another Sandler character marked by loss, disappointment, and a pressure-cooker of self-loathing. Except Danny is stunted this time not by his lack of accomplishment and ambition, but through his single-minded dedication to being the good father Hoffman's imperious patriarch wasn't.

With Ben Stiller matching him as Hoffman's favored son from a later marriage, Baumbach pairs the two tentatively loving estranged siblings (and their equally damaged sister, played with heartbreaking restraint by Elizabeth Marvel) in a delicately realized portrait of enduring, bracingly comic family dysfunction. (The film plays like the Stiller-starring The Royal Tenenbaums, minus Wes Anderson's formalistic whimsy.) Sandler's Danny, with his neglected limp and his penchant for silly songs and occasional strangled and angry outbursts, derives dramatic power from essentially transplanting one of Sandler's half-formed comic characters into a prestige family dramedy. Some critics claim that Sandler is overrated in departures like this, suggesting that many better actors could play his role just as well. But Baumbach knew that Sandler's skills at underachiever pathos would make Danny Meyerowitz uniquely resonant. 

Available on: Netflix

You'll also love: Five Easy Pieces (1970). The Meyerowitz's art world family dysfunction owes a lot to Bob Rafelson's tale of a former piano prodigy turned rapscallion (played by an Oscar-nominated Jack Nicholson) whose return to his eccentric family's home after his father falls ill dredges up a lifetime of pain. 

Hustle
Credit: Scott Yamano/Netflix

4. Hustle (2022)

Sandler's latest vaults close to the top of his collected filmography — clearly, he's in some kind of post-Uncut Gems golden moment, in which his ambitions as a dramatic actor have taken the wheel. As NBA recruiter Stanley Sugerman, Sandler, a longtime hoops fanatic, is a natural at studying the on-court moves of the players, and communicating coaching tips. (To say he was born for this role is almost an understatement.)

But he truly blooms in his quieter scenes with wife Queen Latifah, expressing the twin desperations of middle age and career inertia. ("Guys in their 50s don't have dreams," Stanley says. "They have nightmares and eczema.") Of course, the movie has a playbook, the same one as Rocky and Hoosiers, but as with any inspirational sports film, a commanding central performance can often elevate things. Sandler seizes the opportunity and goes hard to the net. 

Available on: Netflix

You'll also love: Moneyball (2011). Brad Pitt pulled off a similar maneuver in this underseen sports drama, doubling down on seasoned instincts and quiet charm. A distinctly Redfordian performance, Pitt's turn as an innovative coach trying out a new method is a role the actor should be remembered for, and the beginnings of real onscreen maturity, a phase that climaxed with Once Upon a Time in Hollywood

UNCUT GEMS
Credit: A24

3. Uncut Gems (2019)

"You're just about the most annoying person I've ever met." That's Idina Menzel, playing the fed-up wife of Sandler's Howard Ratner in Benny and Josh Safdie's nerve-shredding Uncut Gems. She's not wrong. Sandler's Howard, an inveterate and impulsive gambler, disreputable New York jeweler, and womanizer, is a motormouthed, immature risktaker. He's also the gem in Sandler's acting crown, largely by virtue of the fact that, while Howard's brashness and boorishness sound like Adam Sandler, Howard Ratner is the least Sandler-like character he's ever played.

Shot with the Safdie's grungy, crackling style, Uncut Gems could have starred a 1970's Al Pacino, as Howard dodges loan sharks, romantic entanglements, and an all-or-nothing scheme involving a valuable opal that hinges, improbably, on the Boston Celtics 2012 playoff run. (Actual Celtic Kevin Garnett plays himself in a drolly effective comic turn.) Is Adam Sandler as good as Al Pacino would have been? Nobody's saying that, exactly. But Sandler disappears into Howard Ratner's self-destructive yet ever-hopeful and sweaty skin like he's never done in any film, and watching Howard's downward spiral evokes familiar and heightened undertones of the actor's career-long run of portraying immature men with outsized dreams. Except this time, there's no soft and silly place to land when things fall apart. 

Available on: Netflix

You'll also love: California Split (1974). The gambling addicts in Robert Altman's California-set comedy may not be as seemingly doomed as Howard Ratner — but then again, they may be. Elliott Gould and George Segal make a perfect pair of bantering, betting buddies, their quest for the mythical hot streak taking them through some very entertaining highs and lows. 

Adam Sandler
Credit: Everett Collection

2. The Wedding Singer (1998)

Robbie Hart is Sandler's early screen persona in whiplash-inducing perfection. A contented wedding crooner left at his own altar, Sandler's Hart underplays his broken heart when confronted by his sister carrying his runaway fiancée's Dear John letter. ("So, it's a bad note then," he processes in the church, countenance frozen in slowly dawning shock.) Then, when his ex returns to explain her reasons, Robbie screws his face into sudden rage, cadence building to inimitable Sandler fury as he booms, "Once again, things that could have been brought to my attention YESTERDAY!"

The thing is, while Robbie is shown as being content with his low-stakes career as the best wedding singer in Ridgefield, N.J., The Wedding Singer isn't about a Sandler character needing to aim higher, so much as a delightful rom-com between two made-for-each-other romantics. Teaming for the first time with eventual three-time screen partner Drew Barrymore, Sandler makes Robbie's mutual attraction to the already-engaged Barrymore a delightfully delicate dance of two eccentrics learning to get out of their own way when it comes to love and expectations. Sandler's gift for musical silliness has never been more effective or charming than in his final, grand gesture aboard an airplane, where his Barrymore-inspired ditty "Grow Old With You" is as irresistible to Barrymore as it's become to real-life wedding couples everywhere. 

Available on: HBO Max

You'll also love: The Awful Truth (1937). Mixing knockabout farce with romance is a tough trick, but this Leo McCarey-directed picture does it with giddy grace. Irene Dunne and Cary Grant are the married couple who, after a series of misunderstandings, head for divorce, only for Dunne to get hilariously creative in trying to win Grant back.

Best Adam Sandler Movies Punch-Drunk Love (2002) Emily Watson and Adam Sandler
Credit: Bruce Birmelin/Columbia Pictures

1. Punch-Drunk Love (2002)

The first director to intuit just what Adam Sandler could do with a character tailored to his raw comic energy, Paul Thomas Anderson wrote Punch-Drunk Love's main character Barry Egan for Sandler. Specifically, Anderson touted Sandler's performance as an on-the-edge rejected ex-boyfriend in SNL's "The Denise Show" sketch, claiming astonishment at the depths of rage and pain Sandler's seemingly mild-mannered character could flip on like a light switch. 

Sandler's Barry, a hustling inventor and socially anxious little brother to many domineering sisters, is — in Anderson's tight and tense, self-described "art house Adam Sandler movie" — all of Happy Gilmore's repressed anger, but none of his cathartic expressions of comic violence. At least until an unlikely love (played with exquisite vulnerability and charm by Emily Watson) comes into his life — and is threatened by an innocent indiscretion involving a phone sex worker employed by mattress store scammer Philip Seymour Hoffman. Anxiously pacing through his self-designed daily routine of loneliness and far-fetched aspirations (in addition to hawking novelty plungers, Barry has cooked up a scheme to get free airline miles via a company's pudding promotion), Sandler's Barry is a riveting portrait of how coiled and dangerous an Adam Sandler character would be without his comic explosiveness to protect him. A pitch-perfect teaming of director and star, Punch-Drunk Love represents Anderson pulling apart Adam Sandler's career and reassembling it as a tour-de-force showcase. 

Available on: HBO Max

You'll also love: Love Liza (2002). Jumping down Punch-Drunk Love's cast list, Philip Seymour Hoffman makes Sandler's Barry Egan look almost well-adjusted in comparison in this tragicomic character study of a man almost literally drowning in grief after the suicide of his wife.

Related content:


Comments have been disabled on this post