Adam Sandler’s Movies, Ranked Worst to Best

It takes a special kind of shitty movie to sweep the Golden Raspberry Awards by winning all 10 categories, a feat no other film has matched to date; receive the prestigious “Worst Movie of the Year” award at the Golden Schmoes; and be viciously mocked on not one but two separate episodes of South Park. A work like that would have to be the cinematic equivalent of belly-flopping into an empty pool from the high dive, right? Adam Sandler’s 2011 movie, where he portrays his own twin sister, is such a film. The thin story revolves around a successful man, Jack, who suffers through a seemingly endless visit by his twin sister, Jill. And despite bering the most annoying human being on earth, she somehow finds herself caught up in a romance with Al Pacino. (The screen legend plays himself, and later admitted he only took the role because he was dead broke at the time and had no other offers.) It’s fun to watch bad movies like Manos: The Hands of Fate or The Beast of Yucca Flats for camp value and ironic enjoyment. But it’s impossible to derive any pleasure from Jack and Jill. It’s an abomination. —Andy Greene

Sandler was 21 and on the verge of breaking big on Saturday Night Live when he made his big-screen debut in this “no-budget” indie — that’s his descriptive, by the way; he regularly breaks the fourth wall to comment on how shitty the production values are — about a waiter on a cruise ship who yearns to be a stand-up. In between Sandler mugging for the camera and acting like Jerry Lewis’ bratty nephew after a sugar binge, the movie cuts away to testimonials from beauty-pageant contestants and shots of models in bikinis. An extremely young Peter Berg and Billy Bob Thornton show up as the managers of a rock star and a heckler, respectively. Milton Berle inexplicably shows up as Milton Berle. To call this unwatchable is too kind. It’s understandable that Sandler later disavowed any knowledge of it after he became famous. We don’t blame you, Sandman. —David Fear

Back in 2014, Sandler signed a multimillion-dollar deal with Netflix that would more or less make the streaming service his production company’s home base for the next decade or so. This Western comedy was his first movie for them, and let’s just say the relationship did not start out on a high. Having been raised by Apache, Sandler’s White Knife is surprised to meet his biological father (Nick Nolte), a notorious bank robber. When Dad goes missing over some hidden loot, he and five of his stepbrothers, a.k.a. the Ridiculous 6 — because, y’know, The Hateful 8! Do you get it? — go in search of their M.I.A. pops. Blazing Saddles this is not, to put it mildly; while we don’t usually place much stock in Rotten Tomatoes scores, the fact that this painfully unfunny film is one of the few to maintain a zero-percent score on the site makes complete sense. We’ll put it to you this way: At one point, a character is hit with a projectile geyser of donkey shit. And by the end of watching this Sandler joint, we knew exactly how that guy felt. —D.F.

After years of seducing women by wearing a fake wedding ring, a plastic surgeon (Sandler) finally meets his soulmate (Brooklyn Decker). She won’t have anything to do with a married man, however, which means the doctor has to convince his single-mom assistant (Jennifer Aniston) to pretend to be his soon-to-be-ex–wife. Then everyone goes to Hawaii, the people who are truly meant to be together finally get together, and many jokes about breasts and weiners are made. The end. This truly awful redo of 1969’s Cactus Flower was the first pair-up of the Sandman and Aniston, and we’re now convinced that the sole reason it exists is to retroactively make the Murder Mystery movies look better. That, and to provide Pizza Hut with a free product-placement ad and underwrite a tropical vacation for the whole cast and crew, which, y’know — mission accomplished on that front. Also, we can’t emphasize enough how a little of a horny Nick Swardson screaming lines in a faux-German accent goes a long way. Not even Dave Matthews picking up a coconut with his butt can save this. —D.F.

It starts with a stag pissing all over Sandler, and only gets more groanworthy from there. (Please do not ask what a “burpsnart” is.) The Sandman gets most of the Grown Ups gang (Chris Rock, Kevin James, David Spade) back together for a sequel, which finds them dealing with their kids getting older, a former bully played by Stone Cold Steve Austin, and a bunch of frat bros led by a backflipping Taylor Lautner. The whole thing ends with a big fight at a 1980s-themed costume party where the old guys kick ass, which pretty much tells you everything you need know. All of the camaraderie that made the first movie work has been leeched out here, and not even the IRL friendship between these comedians can keep it from feeling like one long slog. The best thing you can say about this is that Sandler threw a lot of work to an insane number of SNL alums. The worst thing you can say is that the addition of a twitchy, shrieking Nick Swardson — filling in for an AWOL Rob Schneider as the resident freak — is that he actually makes you miss Rob Schneider. —D.F.

Once upon a time, a cobbler on the Lower East Side comes into the possession of a magic stitching machine. Decades later, his great-grandson Max (Adam Sandler) discovers it in the basement of the family business, and realizes that if he uses the machine to stich up a pair of shoes, he takes on the appearance of their owner. You’d think the combo of the fantastical premise, the indie-film pedigree (director Tom McCarthy also made The Station Agent and Spotlight) and Sandler in serious-yet-whimsical mode would have made this a winner. You’d be wrong in too many ways to count. Even before the movie pits the shy, schlubby cobbler against gangsters and has him killing someone with a stiletto heel while impersonating a transexual — we couldn’t make this up if we tried — the whole thing feels like a huge wrong turn. And despite technically being the lead, the star ends up playing more of a supporting part so that everyone from Method Man to Dustin Hoffman gets to showcase how well they can pretend to be Sandler pretending to be someone else. Nope. —D.F.

Sandler is Jakub, a cosmonaut in the midst of a lengthy solitary space mission who starts to grapple with the personal problems he left behind on Earth. Much to his surprise, however, he receives unlikely counseling from an ancient alien (voiced by Paul Dano) who’s snuck on board. Although Sandler maintains a decent Czech accent throughout — the existential sci-fi film is based on Jaroslav Kalfař’s 2017 novel Spaceman of Bohemia — he doesn’t have the chops to pull off his character’s growing melancholy as he becomes convinced that his emotionally distant wife (Carey Mulligan) has fallen out of love with him. The movie is an intriguing, introspective one-man show, further proof that Sandler (as he neared 60) was still up for risky projects. Even ones that turned out to be noble failures. —Tim Grierson

In the Nineties and early 2000s, Sandler earmarked Drew Barrymore as his go-to romantic comedy partner. For the next two decades, however, he’d turn to his friend Jennifer Aniston whenever he needed a rom-com co-star, starting with this film’s antecedent, Murder Mystery. The two reunite for this Netflix sequel, which continues the adventures of unlucky travelers Nick and Audrey Spitz. After catching a killer in the first film, they’ve traded in their lives as a cop and a hairdresser to become full-time private detectives, and their skills are put to the test when an old friend is kidnapped during his extravagant wedding. Murder Mystery 2 ups the action and adds an intriguing supporting cast — including Mark Strong, Mélanie Laurent, and Jodie Turner-Smith — but forgets that the most important ingredients for a comedy and mystery are… comedy and mystery. In the end, the chemistry of Sandler and Aniston can only solve so much. —Derek Lawrence

The kindhearted, accented simpleton that Sandler mastered in movies like The Waterboy returns in this mostly limp Halloween-themed film whose main fun is a game of “Spot the celebrity!” (Shaq! Buscemi! The Commish! Stiller!!) Blessed with the name Hubie Dubois — because “Bobby Boo-chez” was presumably too obvious — Sandler’s title character is his town’s local self-appointed “Halloween monitor,” tasked with ensuring everyone stays safe until a series of kidnappings rock the community. Like the film itself, no one really asked for Dubois to create anything more than a mildly pleasant distraction. Still, the script, written by Sandler with frequent collaborator Tim Herlihy, does add “horror comedy” to Sandler’s oeuvre. Now parody Cannibal Holocaust, Sandman. —Jason Newman

A second attempt to recreate the chemistry between Adam Sandler and Drew Barrymore from The Wedding Singer. The pair do have an authentic rapport — Sandler’s stunted-adolescence masculinity pairs well with Barrymore’s ditzy charms — but their banter isn’t enough to save this movie’s tortured conceit. After a bad blind date, a widowed family man (Sandler) and a single mom with a lousy ex (Barrymore) find themselves accidentally sharing the same luxury trip to Africa. Yikes. Sandler is at the top of his sensitive every-bro game here, and no one does exasperated like Barrymore, but nothing can save this will-they-won’t-they rom-com-meets-The Lion King debacle. Speaking of: The African scenes are impressively cringe. —John DeVore

Sandler is actually one of the few bright spots in Jason Reitman’s well-meaning yet inert ensemble drama about the perils of our internet-obsessed culture; he’s an unhappy husband looking for human connection via online escorts. It’s mildly fascinating to watch him play a different kind of socially awkward beta-male with a penchant for sex workers more than a decade after Punch-Drunk Love. And indeed, a sad-sack character who could have been played for laughs is, instead, humanized by the sadness and gentle awkwardness the star brings to the role. But his best efforts are wasted in a film that’s too invested in viewing all of its characters as tragic symbols of online addiction, sucking the spark out of Sandler in the process. —T.G.

The end of this Sandler melodrama finds a psychiatrist noting his character’s “incapability to function in anything resembling a normal, adult manner.” Sure, that describes 90 percent of the man-boys Sandler plays. But in this gripping character study-cum-tonal mess, exclamations like “Stop looking at me, Swan!” are replaced with [checks notes] Sandler choking back tears as a 9/11 widower wracked with PTSD, memory loss, and delusional tendencies five years after his wife and three kids were killed. When his college roommate (Don Cheadle) — who’s also going through an exponentially less severe, if equally existential, life examination — reconnects with his old friend, the duo embark on a buddy film that mixes untold wellsprings of tragedy with maudlin uplift and ludicrous subplots. There’s a fumbling clumsiness to director Mike Binder’s earnest attempt at navigating unimaginable grief, but it’s almost worth it to see Sandler’s early attempt to flex his range. —J.N.

In the first genuine live-action “family film” of his career, Sandler portrays a down-on-his-luck hotel handyman forced to watch his sister’s kids while she’s out of town. His luck turns around when he discovers the bedtime stories he tells the kids every night come true the following day, even if they involved gumdrops falling out of the sky or other magical elements. He attempts to manipulate this force for his own benefit, but in the grand tradition of The Monkey’s Paw, the wishes have a habit of backfiring in unpredictable ways. The cast is rounded by out by Keri Russell, Courteney Cox, and Russell Brand, and there a few genuine laughs. But most families are better off watching Billy Madison and Happy Gilmore if they’re looking for harmless entertainment. And it’s not surprising Sandler never again attempted a movie aimed entirely at children. —A.G.

They’re Saturday Night Live superstars with the same initials — it was only a matter of time before Adam Sandler and Andy Samberg did a father-son buddy comedy together, amirite? The Sandman is a former tabloid celebrity, having once had an affair with his eighth-grade math teacher when he was a teen; the Lonely Islander plays the offspring of that relationship, who’s now a financial-industry whiz and wants nothing to do with his deadbeat dad. Except Pops owes $43,000 in back taxes, and the only way he can get the dough in time is to crash his son’s wedding weekend and convince him to do a family-reunion TV special at Mom’s prison cell. Even by Happy Madison Productions’ standards, this gross-out comedy takes extra pride in being as crass and crude as possible, and the dynamic of Sandler in party-animal mode and Samberg’s dweebish beta dude wears out its welcome way too soon. Still, if you’ve ever wanted to see Luenell shoot baseballs out of her hoo-ha, Sandler masturbate to a picture of someone’s grandmother, or ride shotgun with the SNL veterans and Vanilla Ice on a drunken vandalism spree, this movie’s for you. —D.F.

The Just Go With It duo of Aniston and Sandler reunited for what would turn out to be a Netflix franchise, playing a married couple named Nick and Audrey Spitz. They finally go on their long-promised European honeymoon, only to get more excitement than they bargained for. When Audrey meets a mysterious stranger (Fast & Furious star Luke Evans), she and Nick land in the middle of a whodunnit and rush to prove their innocence. The movie rests firmly on the shoulders of its two stars and their warm dynamic, and they’re almost enough to make this a worthy trip. Almost. —D.L.

Hot on the heels of the breakthrough blockbusters The Waterboy and Big Daddy, Sandler decided to unleash one of his weirdest mainstream movies. And really, there’s no way to defend this coarse, homophobic fantasy-comedy about Satan’s sweet misfit son Nicky (Sandler), who must travel to Earth to convince his evil brothers to return to Hell. To his credit Sandler (who cowrote the movie) certainly commits to the absurdity, playing Nicky as a wildly ineffectual, emo-hair-sporting weirdo with a speech impediment to boot. Tacky and tasteless — there’s a running joke involving Kevin Nealon’s Gatekeeper of Hell having boobs on his head — the movie deservedly bombed, temporarily stalling the Sandman’s superstar momentum. Still, the film has a cult following thanks to Sandler’s profoundly bonkers portrayal. He’s never been so consciously off-putting, which gives this comedic train wreck a strangely hypnotic pull. You can’t look away from its awfulness. —T.G.

Almost seven months to the day after Happy Gilmore promised great things for Sandler’s inspired style of oddball hilarity, this wan action-comedy (which he didn’t write) suggested that he still didn’t understand his own strengths. He and Damon Wayans play Southern California crooks, except Wayans is actually working undercover for the LAPD and arrests his buddy, setting in motion a Midnight Run-esque buddy film in which criminal and cop go on the road together to avoid a ruthless drug kingpin. At this early stage of his big-screen career, Sandler seems terribly uncomfortable portraying a normal human being, while his occasional forays into his trademark shtick get hemmed in by the derivative script. In hindsight, what’s most striking about Bulletproof is how boring it is — a criticism you could hardly level at Sandler’s ingeniously sophomoric comedies of the time. —T.G.

Sandler had never worked alongside an icon of Jack Nicholson’s stature when he signed up for this contrived comedy about a mild-mannered everyman who finds his life turned upside down by a heralded but unconventional therapist assigned to “help” him with his supposed anger issues. This team-up also represented a change of pace for Sandler in that, for once, he was the one playing the relatively reserved character, while his Oscar-winning costar hammed it up mercilessly. That such a strained premise ended up becoming a hit movie proved that Sandler had a future portraying regular, buttoned-down guys. But the lack of chemistry between the two leads and the increasingly stupid storyline left longtime fans wishing he’d cut loose like in the old days. —T.G.

Writer-director Nora Ephron’s Christmas movie about folks working at a suicide-prevention hotline on Christmas eve isn’t exactly essential holiday viewing, though it has its fans. And even though this ensemble comedy has a to-die-for cast — Steve Martin, Madeline Kahn, Juliette Lewis, Liev Schreiber, Parker Posey, Jon Stewart, Rita Wilson, Anthony LaPaglia, Robert Klein, Garry Shandling — you’d be surprised how few laughs there are in this overly sentimental, tinseled schmaltz. Sandler is actually one of the highlights, playing a wacky, ukulele-playing neighbor who’s a variation of the guy who’d show up on SNL‘s “Weekend Update,” singing about his red-hooded sweatshirt (with a bit of Canteen Boy and the house-sitting Herlihy kid thrown in for good measure). In some alternate universe, there are Christmas carolers singing about their deep love of grape jelly every December. —D.F.

Thirteen-year-old Sam Zimmer’s one talent in life was mastering the first generation of arcade games (your Centipede, your Galaga, your Donkey Kong) back in the summer of 1982. In the 21st century, however, that doesn’t mean squat. Except, for reasons that are too complicated to get into here, aliens have decided to destroy Earth via challenges based on those old video games. Now, at the request of his childhood best friend (Kevin James) — who happens to be the President of the United States — Zimmer (Sandler) and the sleazy felon (Peter Dinklage) who once beat Zimmer in the world arcade-game championship have become humanity’s last hope. You can see how the makers of this would-be summer blockbuster studied the Ghostbusters template in an attempt to sell Sandler as a Bill Murray-type action-comedy smartass hero. And you can also see how they totally manage to fall short of replicating that same formula with a recognizable bunch of old-school video-game characters instead of sliming paranormal spirits. If you’ve ever wanted to see a giant Pac-Man try to eat midtown Manhattan, this may be your jam. Otherwise: It’s game over from the get-go. —D.F.

This crude comedy hit a cultural sweet spot between post 9/11 first-responder worship and pre-Supreme Court ruling in favor of same-sex marriage. A widowed firefighter (Kevin James) asks his womanizing best friend (Sandler) to enter into a domestic partnership to circumvent the red tape of his pension. The movie is both homophobic and begrudgingly open-minded — an extremely awkward mix. Sandler’s character constantly asserts his masculinity, anturally, and boy, does this schtick gets tedious. Eventually, very light “love is love” lessons are learned. The two stars are funny together, with James doing the heavy lifting of delivering a semi-believable and likable performance. As for Sandler, he just keeps mugging. —J.D.

If you’ve ever wondered what Sandler translated through the lens of James L. Brooks would look like, here’s your answer. It’s a well-meaning if slightly offensive romantic comedy that sees Sandler playing John Clasky, a celebrated Los Angeles chef who’s married to a high-strung exercise-a-holic, and slowly falls for his Mexican immigrant housekeeper, Flor (a luminous Paz Vega, who steals the show). She’s a warm yet feisty single mom who comes to America to give her young daughter a better life, and whose parental authority is routinely undermined by her rich white bosses. Sandler is a bit constrained in a more conventional role, but the great Cloris Leachman steps up to provide comic relief as John’s live-in mother-in-law, Evelyn, never without a martini or bottomless glass of wine and a smart remark. —Maria Fontoura

Inhabiting the role originally played by Burt Reynolds, Sandler had big cleats to fill in this remake of the 1974 prison-football movie. But he pulls it off by mixing a little human heart with the humor. As Paul Crewe, a disgraced NFL quarterback who violates probation and ends up in the can, Sandler leads a team of inmates onto the gridiron to appease a sneaky warden. But before he can put a squad together, Crewe has to win over his fellow cons. As the convict says to one hulking inmate: “I’ll teach you to football.” It may not be the touchdown that Reynolds’ classic was, but it’s at least a two-point conversion. —Joseph Hudak

If you squint enough, this 2006 Sandler vehicle could be mistaken for a dirtbag Gen X remake of It’s A Wonderful Life — and the star is surprisingly good in the role of an ambitious middle-class workaholic who comes across a magical universal remote control that actually controls the universe. He uses the device to pause and fast-forward through his life, and it’s all fun and games until he starts missing important moments with his family. Supported by legends like Henry Winkler and Christopher Walken, Sandler really pushes the emotional boundaries of his frat boy persona in this Twilight Zone-y fantasy. Yes, of course there are sudden, unnecessary, off-color gags. But it’s also attempting to sell a pop meditation on regret in between the crass asides. Who knew Sandler could sob so believably? —J.D.

High school reunions are hell — this is a scientific fact — and for a bank manager named Charlie (David Spade), a get-together with his former teenage peers is yet another reminder of his failed marriage, his failed career prospects and his overall failed life. Luckily for him, his old buddy Max (Sandler) has a solution: They both fake their own deaths and, courtesy of a key found up a dead man’s ass — don’t ask — the two men have new identities, access to untold riches and possession of a dream house in Puerto Rico. Unluckily for Charlie, they’ve taken the names of men wanted by some very bad people. Gymnastic assassins, gay bikers, the cure for cancer and Kathryn Hahn, respectively, all come into play as well. Sandler is the risk-taking alpha to Spade’s cowering beta, and though his character isn’t the brightest guy in the world, he’s way more of a badass than the star’s usual hedonistic every-bros. The whole thing feels like a transmission from an alternate universe in which Bulletproof is the biggest blockbuster ever made, and Sandler then spends the rest of his career doing nothing but action-buddy comedies. —D.F.

They were the “Ferdinando Five,” the teens who won the junior-high basketball championship back in 1978. Now, those five best friends are fortysomething adults with families, jobs and the responsibility of burying their beloved Coach Buzzer. But what is a funeral, if not a great excuse for a three-day reunion at the old lake house with their conspicuously gorgeous wives and spoiled offspring? The fact that Sandler surrounded himself with his actual buddies — Kevin James, Chris Rock, David Spade, and Rob Schneider — gives the whole film a sort of “how I spent my summer vacation filming a gross-out comedy with my pals” vibe. And the obvious sense of fun these guys are having together is contagious enough to counteract a lot of “these kids today!” griping and low-hanging-fruit slapstick. (We hope James got paid by the pratfall.) Bonus points for the dad-friendly classic rock soundtrack, Maya Rudolph slaying every one of her punch lines, and some first-rate trash-talking, especially about Schneider’s overly sentimental, creepy dude with the bad Elvis toupee and PDA with his much older wife. —D.F.

“The Citizen Kane of alcoholic clown movies” was a hell of a next-level marketing slogan in 1992, and Bobcat Goldthwait was years ahead of his time with this brilliant cult classic, directing and starring in the surreal comedy about a down-and-out clown with a nasty drinking problem. Shakes battles rodeo clowns, parties hard down at the Twisted Balloon, and hits bottom. But Sandler, still a virtually unnoticed ingenue on Saturday Night Live, is unexpectedly tender in a minor role as a fellow clown worried about his buddy Shakes. With great turns from Robin Williams, Julie Brown, and LaWanda Page, this remains a pioneering satire—it’s not often you can say that about a movie that opens with Florence Henderson brandishing a giant hickey on her throat. —Rob Sheffield

This lighthearted coming-of-age story is, like many of Sandler’s later films, a family affair. He stars as a Teddy Bear of a father whose youngest daughter is hurtling towards her bat mitzvah; she’ played by Sandler’s real-life daughter Sunny, who plays a perfectly charming, hormonal teen. Sandler’s wife, Jackie, and his naturally deadpan eldest daughter, Sadie, have smaller but memorable roles. It’s a heartfelt teen comedy with some genuinely funny moments, and Sarah Sherman stands out as a hip rabbi. This might be Sandler’s peak form: the adolescent rage fits are still there — in small portions — but The Sandman is firmly middle-aged now, with his share of patrernal wisdom and experience under his belt. — J.D.

Sandy Wexler may be a Hollywood agent whose clients range from ventriloquists to the world’s most accident-prone daredevil, but he’s also the type of Tinseltown legend beloved by everyone from Lorne Michaels to Vanilla Ice. After noticing a singer named Courtney Clarke (Jennifer Hudson) at at a Magic Mountain kids show, he convinces her to sign with him and promises to make a star. His discovery does indeed become the greatest musical sensation since Whitney Houston — which means it’s just a matter of when, not if she’ll become too big for Sandy. This is Sandler’s attempt to do his own version of Broadway Danny Rose, complete with a million cameos from his famous friends and peers. It’s one of his stronger Netflix films, to be sure, and you can tell the comedian has a real soft spot for old-school, larger-than-life types happy to wallow in the shallow side of the industry pool. Why Sandler and his cowriters decided to turn it into a rom-com (!?) in the third act is, frankly, a mystery. And if you’re allergic to sentimentality, you may want to cut out before the “There’s No Business Like Show Business” sing-along at the end. —D.F.

Sandler has always had a little metalhead in him and he played it to the hilt in this 1994 comedy about a hapless rock band — even their name, the Lone Rangers, is a contradiction — that inadvertently takes a local radio station hostage to get their demo played on air. As the group’s drummer Pip, Sandler (decked out in a purple beanie and cut-off flannel) is lovably clueless. In one of his best scenes, he tries to make a break for it to the band van, which allows him to show off his gift for goofy movement. When the cop cuts Pip off, he launches into an inspired dance and bolts back inside: “I don’t wanna go to jail,” the drummer cries, “I’m fragile.” —J.H.

Or: What if Father of the Bride starred the Sandman instead of Steve Martin? All Kenny Lustig (Sandler) wants is to marry his oldest daughter off in style, and prove that he doesn’t need any help, financially or otherwise, from the groom’s father Kirby (Chris Rock), a wealthy, philandering surgeon. Meanwhile, his house in Long Island is turning into a makeshift hotel for everybody’s relatives, and the “suite” where he’s set up his rich counterpart is constantly falling apart. Sandler cowrote this wedding comedy with director Robert Smigel, and you can feel the legendary SNL writer’s subversive sense of humor adding a nice edge to everything — especially when the films skirts right up to the line of good taste with jokes centered around Kenny’s legless uncle, played by the late actor Jim Barone. It’s also surprisingly sweet even at its raunchiest; Sandler’s screaming duets with Rachel Dratch are top-notch; and his polite yet on-the-edge dad feels like a kinder, gentler version of his powederkeg Punch-Drunk Love character. —D.F.

In December 1994, months before he was fired from Saturday Night Live for reasons to still remain very difficult to understand, Adam Sandler unveiled “The Chanukah Song” to the world during an appearance on Weekend Update alongside his good buddy Norm McDonald. He saw it as little more than a one-off goof, yet the tune has had an incredible afterlife — Sandler has re-written the song top-to-bottom four different times, and it gave him the inspiration to create the 2002 film. His character Davey Stone is an alcoholic loser who finds purpose in life when he’s forced to volunteer for a New Hampshire youth basketball league during the holidays; he also voices an elderly referee and his twin sister. By Sandler’s standards, the movie woefully under-performed at the box office, and though he’d lend his golden pipes to other animated films (Leo, the Hotel Transylvania series), this was the last time he attempted a cartoon based directly on his work and persona. —A.G.

For the first time, Sandler and his longtime collaborators — notably writer Tim Herlihy and director Stephen Brill — remade an Old Hollywood classic, the 1930s Frank Capra / Gary Cooper vignette Mr. Deeds Goes To Town. He plays Longfellow Deeds, a small-town New Hampshire pizza guy who suddenly inherits a billion bucks. It was also Winona Ryder’s last hurrah, released right after her controversial shoplifting bust, when she took a long hiatus from movie stardom after her unbroken 16-year run as America’s Gen X grunge-moppet sweetheart. (Free Winona, now and forever.) Steve Buscemi damn near steals the show as Mr. Deeds’ chaotic pal Crazy Eyes. But the Sandman swipes it back with arguably the finest deployment of a David Bowie song in any Hollywood movie, when Deeds celebrates his first helicopter ride by belting “Space Oddity.” —R.S.

Big Daddy takes a philosophy established in Billy Madison — “If peeing your pants is cool, consider me Miles Davis” — and essentially extrapolates it to an entire movie. It’s Sandler in dad mode, sort of, as Sonny Koufax, an unemployed law-school grad living off a pile of cash he got in an accident payout, who “adopts” a five-year-old kid named Julian to prove to his ex-girlfriend that he’s capable of being a grown-up. He lets the kid (played by twins Cole and Dylan Sprouse) eat 30 packets of ketchup for lunch, watch garbage TV, dress in crazy outfits, and call himself Frankenstein. But gradually, as the two wreak havoc around Manhattan, pissing in doorways and tripping roller-bladers, some lessons are learned, and actual growing up takes place. And though Sonny will never stop making fun of his buddy’s fianceé for that time she worked at Hooters, he’s still a nice enough guy to convince a cool new pretty lady (Joey Lauren Adams’ Layla) to fall for him. Who wouldn’t? —M.F.

Before either of them would revolutionize screen comedy in their own distinct ways, Sandler and Judd Apatow were just two struggling comics living together in North Hollywood. So when the filmmaker decided to make a film about a rich and famous movie star finding out he has a terminal disease, he called on his former roommate to play, yes, the rich famous movie star. It’s tempting to look for autobiographical details in Sandler’s character George Simmons, especially since the blockbusters that got him an the A-list — one about a merman, another about an adult who’s transformed into a wisecracking baby — are the kind of films that resemble those on the back half of this list. Regardless, you can feel Sandler leaning into the fact that Simmons is a narcissistic asshole, and the lack of sentimentality or touchy-feely life lessons makes it seem like you’re watching a game of celebrity chicken. There’s no flinching on his part. “You’re the only person I know who’s learned nothing from a near-death experience,” he’s told by Seth Rogen’s aspiring comedian-slash-joke-writer-slash-personal-assistant, and even when it seems like Simmons will find true romantic happiness in Funny People‘s sixth act (just sayin’, this movie is extremely long), Sandler doesn’t sand down the edges. Fans may have rejected this semi-sour look at Hollywood haves and have nots. But you have to admire what the star is doing here. —D.F.

It wasn’t like Sandler hadn’t done sequels before (you’ll notice a couple of movies on this list with a “2” at the end of their titles). But it took nearly 30 years to give fans the follow-up they truly, madly, deeply wanted. And trust us when we say the Sandman made this continuation of the Saga of Happy Gilmore — hockey lover, legend of the links, idol to golf bros around the globe — was made with the die-hards in mind. Virtually all of your favorite characters from the original are back, while a graveyard brawl doubles as a tribute to the ones (Barker, Grandma, the “Jackass!” guy) played by actors who’ve gone to that great fairway in the sky. Many of your favorite jokes and quotes get a shout-out or a reprise. It’s total nostalgia-bait, to be sure, but it’s also a sequel that harnesses in the good energy of HG 1 and blocks out the bad that usually accompanies number two’s. Harness. Good. Block. Bad. —D.F.

In this vastly underrated sports movie, Sandler plays Stanley Sugerman, a beleaguered scout for the Philadelphia 76ers who’s got about five minutes left on his lifelong dream to be an NBA coach. The owner (Robert Duvall) believes in him, making Sugerman an assistant. But his sniveling son (Ben Foster) takes over the team and sends Stanley back on the road. Luckily, Stan stumbles on Bo Cruz (NBA journeyman Juancho Hernangómez), a playground hustler in Spain. And a double-underdog story is born. The Sandman carries the movie on his back, playing Stan with a blend of serious-Sandler chops and the flat-voiced sarcasm we know and love. It’s Punch-Drunk Madison meets Jerry Maguire. —M.F.

Sandler enlisted Robert Smigel and Judd Apatow to write a film based on an Israeli Mossad agent with one real dream: to cut and style hair and “make people silky smooth.” After faking his death and moving to New York, Zohan lands in a Palestinian barber shop, where this virile hairdresser’s penchant for cutting bangs is rivaled only by his ability to bang his greying clientele. With an unhealthy obsession for hummus, comically oversized bulge, and a love of loud shirts that are allergic to closed buttons, Sandler attempts to bring levity to a perilous situation. Bonus points for the many cameos, including Chris Rock, Henry Winkler, Mariah Carey, and, most oddly, Dave Matthews as an inept white supremacist. —J.N.

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.

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.

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.

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.

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.

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.

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.

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.