Adam Sandler is many things to many people – a comedy icon, writer of "The Chanukah Song," star of Netflix’s upcoming Murder Mystery 2 – but he has rarely been a critical darling. Sandler’s lucrative comedies have consistently struck out with critics, the exception being when the onetime SNL phenom veers into the realm of drama with the likes of Uncut Gems, Punch-Drunk Love, or The Meyerowitz Stories. His recent foray into the Netflix drama Hustle is more evidence of that.
The truth, however, is that not every Adam Sandler comedy is created equal. Some are transcendental, others are merely passable. Some are forgettable and benign, others are accidentally fascinating (Sandy Wexler and Jack & Jill both come to mind in this specific regard). Sandler is not only one of our more popular funnymen: he’s also a rather prolific movie star, period, giving audiences a star vehicle every year or two, in addition to the Happy Madison flicks that feature pals like David Spade and Kevin James. With a body of comedy work this extensive, it only stands to reason that there would be some duds in the mix.
This is not a list of Adam Sandler’s worst movies. This is a list of Sandler’s best and funniest movies: the all-timers, the hall-of-famers, the ones that make you cry laughing when you quote the best lines to your friends. As the Sandman himself might say, these movies are “not too shabby.”
10. Little Nicky
The plot synopsis for Little Nicky – the slack-jawed son of the devil teams up with a talking bulldog and two metalheads to thwart a plan that involves his evil brothers seizing control of their father’s throne and destroying New York City – sounds like it was dreamed up on a stoned dare between overstimulated 16-year-old boys. Steven Brill’s unhinged, expensive, critically-loathed cult classic is certainly not the most polished Sandler comedy, and yet, it’s difficult to concede that this giddy Satanic jape is as much of a blank-check indulgence as anything its star has made since. Plus, compared to some of today’s more timid studio comedies, this thing actually has a comedic point-of-view! Given Sandler's rash of sports movies and love of the game, this one had to make the list.
9. Hubie Halloween
The anarchic and uproarious Hubie Halloween is as close as Sandler has gotten to the inspired madness of his early work in a long time. What’s more is this thing is downright wholesome: Hubert Schubert Dubois is another one of Sandler’s unforgettable, mush-mouthed, small-town folk heroes, a victim-turned-savior who single-handedly protects his Salem hometown from spooky Halloween forces with nothing more than some practical know-how and his trusty, multipurpose Thermos. Hubie is so unaffectedly pure and is such a good time – not to mention, really, truly funny, in the way that Caddyshack or The Zucker Brothers are funny – that it managed to win over even those who normally consider themselves averse to Sandler’s charms.
8. The Week Of
One of the loveliest surprises in Sandler’s entire body of work, The Week Of is the genial, relaxed Happy Madison version of a Mike Nichols or James L. Brooks slice-of-life dramedy. The movie sees Sandler beautifully playing an overcompensating, over-leveraged Long Island family man, who is desperate to impress his wealthy and emotionally distant in-laws, the patriarch being Sandler’s former SNL pal, Chris Rock. Directed by frequent Sandler collaborator Robert Smigel, The Week Of is a subdued, character-focused gem that occasionally throws in jokes about drunk old men and giant burlap sacks filled with bats to please day-one Sandler devotees. But it is largely content to unfold as a wistful and soft-tempered meditation on family and commitment.
7. You Don’t Mess With The Zohan
Adam Sandler’s answer to the Israel/Palestine conflict is one that involves hacky-sack played with a live feline, inventive use of hummus (pro-tip: you don’t always have to eat it), a fictional, wildly addictive soft drink called “fizzeh bubbeleh,” and the Sandman himself as a buff, seemingly unkillable ascendant hairdresser named Zohan Dvir. You Don’t Mess With The Zohan is also a sweet movie in its own goofball way and without question the loopiest Sandler comedy since Little Nicky. What’s more, is that the film’s villain is a Trump-style white nationalist tycoon: it’s a curious narrative decision that calls the famously Republican Sandler’s political leanings into question.
6. Big Daddy
It’s not hard to see why Big Daddy remains one of Sandler’s most beloved movies. Here, once again, in the wake of The Wedding Singer, there was a shift in focus: away from Sandler’s goonier side and towards his more quietly implosive, fascinatingly passive-aggressive tendencies as a screen performer. Could Happy Gilmore director Dennis Dugan be the one to successfully mine Sandler’s soft sensitivity, buried deep as it was beneath an avalanche of fury? We’d say so. Big Daddy is slaphappy, shameless, and heart-warming, and the movie’s occasionally saccharine tone is compellingly offset by an insistent mean streak, and also hard-won wisdom about what it means to actually grow up and leave childish things behind.
5. 50 First Dates
50 First Dates wasn’t just a bounce back after the wonky Anger Management. This Groundhog Day-inspired rom-com is easily the breeziest and most charming Sandler comedy since the star’s terrific mid-90s run. Sandler is almost doing a Walter Matthau riff here, playing a slick, cynical, Hawaii-bound womanizer whose cold heart is inevitably thawed by his old Wedding Singer co-star, Drew Barrymore. Sandler and Barrymore are brilliant as a screen couple because they share the chemistry of dorky adolescents who are just beginning to learn how much they like each other; what’s more is that the movie showcases a softer, more compassionate Sandler without sacrificing any of the bizarre gross-out humor (hello, steroid-abusing Sean Astin) that his fans love him for.
4. The Waterboy
Sandler inched dangerously close to mainstream respectability with The Wedding Singer, so it only stands to reason that The Waterboy is the dumbest and most puerile of his early run of slob comedy milestones. It’s almost as if Sandler and his cohorts wished to make something explicitly for the fans of the actor’s insane, pre-fame comedy records, which make no attempt to cross over to a non-Sandman audience. It helps that The Waterboy is also incredibly funny: an affable underdog-pigskin saga with one of Sandler’s trademark warbling nerd kings, Bobby Boucher, at its mushy center. And like all the great Sandler movies, The Waterboy is resoundingly good-natured: the tale of a sheltered, yet valiant, mama’s boy and the physically dangerous things he’ll do for his mother’s love.
3. Happy Gilmore
This is the blockbuster wherein Sandler’s volcanic temper made him one of Hollywood’s most in-demand comedy stars. The character Happy Gilmore is, by any metric, a psychopath with serious rage-control issues. However, because Happy is channeling his latent capacity for violence in order to win a golf tournament – thus getting one over on the 1%’er elite and saving his sweet grandmother’s house from foreclosure in the process – we come to love him. It certainly doesn’t hurt that Sandler plays Happy with a kind of bruised puppy-dog integrity. Sandler has given us bawdy sports romps before, but never funnier than this, and Happy’s frightening game-day meltdowns are the stuff of comedy legend, while the savagely protracted fist fight with Bob Barker is inarguably one of the greatest things that Sandler and his team of collaborators have ever filmed.
2. Billy Madison
Here it is, folks, the first canonical Sandler work: a trailblazing progenitor that’s so fearlessly immature and over-the-top ridiculous that it ends up transforming a fairly stock comedic scenario into something deranged and very nearly avant-garde. Billy Madison’s entirely nonsensical setup at once allows the Sandman to indulge in his nostalgia for vaguely aspirational 80s comedies like Back to School (starring his hero and comic forefather, Rodney Dangerfield), and yet Billy, in spite of its air of juvenile, surreal, nose-thumbing offensiveness, allows for a sneaky critique of upper-crust white privilege that belies Sandler and Tim Herlihy’s screenplay’s proudly doofy frat-boy façade. There are jokes about flaming bags of dog poop, hallucinated penguins, Norm Macdonald, Chris Farley as an out-of-control bus driver, and a cameo from a murderously unbalanced Steve Buscemi. Are you sold yet?
1. The Wedding Singer
This one remains one of the most radiant love stories of the 90s, despite being very much set in a delirious, hilariously heightened version of the 1980s. To this day, this contemporary classic about an underappreciated cocktail waitress and a moody wedding singer, who fall in love in small-town suburban America, bonding over silly sing-a-longs, heart-to-hearts, and gawky middle-school intimations, remains one of the most purely likable movies of its decade. This is the one that even Sandler haters seem to make excuses for, that’s how downright Old-Hollywood wonderful it is. Frank Coraci’s official directorial debut, which is as disarming as The Philadelphia Story, if not quite as elegant (psh, elegance), also proved that Sandler possessed the chops to be a bonafide romantic lead without sacrificing the lowbrow frivolity (horny rapping grandmas, volatile outbursts, Steve Buscemi being a drunken lout) that ultimately made him a star.