The Five Absolutely Essential Adam Sandler Movies
Welcome to “Five Absolutely Essentials,” an overview of the greatest comedians’ most memorable moments. Mind you, these aren’t necessarily their “best” movies — rather, these are the five films that best represent different aspects of their talent, their ambition, their persona and the artistic risks they’ve taken along the way. If you’re looking for a sense of a comic in all his or her complexity, here’s where to start.
Adam Sandler doesn’t do a lot of interviews. They’re not how he likes communicating with the world. “I decided I wanted to talk through what I like to do,” he recently explained to The Washington Post, which was profiling him in preparation for his receiving of the Mark Twain Prize for American Humor. “I like to do my stand-up. I like to do my movies. I was just happy doing that.” Starting out on Saturday Night Live and then making the jump to movies, the 56-year-old is beloved by audiences and, belatedly, by journalists and critics who were once chilly to his antics. But Sandler ignored the haters and just kept doing his thing, letting the work speak for him. He got the last laugh.
His stardom has been different from those of other former SNL figures. Unlike Mike Myers, he doesn’t have a blockbuster franchise. (The Hotel Transylvania series is probably the closest he’s gotten?) Unlike Will Ferrell, his mainstream comedies weren’t trying to comment on larger themes. Quite simply, Sandler’s movies are just funny, and his instincts for what a large audience craves in a comedy have been fairly unerring. Add to the fact that he cultivates a creative family of directors, writers and co-stars who keep popping up in his films, and you can understand why he’s viewed so warmly. Maybe he hasn’t made a slew of masterpieces, but anytime one of his flicks is on cable, it’s hard not to watch until the end. They reward endless revisits.
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What’s challenging about selecting five essential films for Sandler is that he has occasionally ventured far from his comfort zone, resulting in some of the finest work of his career. You can’t pigeonhole the Sandman, who can go incredibly broad but also be incredibly moving depending on the character he’s playing. Frankly, five films aren’t enough to encapsulate the impact he’s had on Hollywood and comedy fans. But these are a good place to start.
Billy Madison (1995)
Sandler had been in movies before this 1995 breakthrough, but here’s where he delivered his first proper starring vehicle. Billy Madison successfully transplanted Sandler’s Saturday Night Live persona to the big screen, letting him play a goofy overgrown kid whose utter stupidity made younger viewers laugh while their parents and critics just shook their heads. Sandler wasn’t expecting the negative reviews that came his way.
“When Billy Madison came out, me and my friend who wrote it, we were just like, ‘Oh yeah, they’re going to write about this in New York!’” he recalled last year. “We grew up reading the papers, we were going to NYU. And then we read the first (review), and we were like, ‘Oh my god, what happened? They hate us.’ And then we were like, ‘It must have been this paper,’ but then 90 percent of the papers are going, ‘This is garbage.’”
Sandler quickly learned to stop reading reviews, and he refused to “grow up” to please his naysayers. A few decades later, Billy Madison’s juvenile worldview is embraced as cockeyed genius, the movie responsible for launching dozens of memes. What’s no doubt helped is that, with hindsight, we can see the clear intelligence at work behind all those super-silly gags — and the absolute joy Sandler had portraying an idiot.
Happy Gilmore (1996)
The best of Sandler’s early broad comedies, Happy Gilmore came out just a year after Billy Madison, but you could already notice his confidence growing as a movie star. And while no one would describe Happy Gilmore as “sophisticated” — after all, this is a film in which Sandler gets in a fistfight with Bob Barker — the jokes are sharper and more plentiful. Plus, the volatile Happy Gilmore, a failure at hockey who discovers he’s got a gift for golf, was an even funnier character for Sandler to play. And if all that wasn’t enough, this film gave the world Shooter McGavin (Christopher McDonald), one of the best sports villains ever.
“Being in an Adam Sandler movie is such a joy, because everything is light, funny and improvisational,” McDonald said in 2021. “He surrounds himself with his boys and his friends. … He really wanted to put a spin on the sports genre. Happy hates the game and the jerks playing with plaid suits, so he comes out with his combat boots and hockey T-shirts.”
The film’s slob-versus-snob dynamic between Sandler and McDonald was superbly executed, and Sandler even managed to come across as a believable romantic foil once Happy woos Julie Bowen’s friendly PR director. Happy Gilmore was before mega-hits like The Waterboy and Big Daddy, but its inspired strangeness makes it still one of his highwater marks. And c’mon: That fight with Barker is pretty great.
Punch-Drunk Love (2002)
“It felt like a free gift from a guy who called me up and said, ‘I wrote you a movie,’” Sandler said in 2022 while looking back at the film that first demonstrated his potential as a dramatic actor. “When that happens, it’s incredible. You’re just like, ‘Okay, man, thanks.’ I knew it was different. But I just followed what the man told me to do. I was excited.”
He, of course, is talking about Paul Thomas Anderson, who was convinced that the Sandman was the right man to play Barry, a lonely, troubled Angeleno who falls for shy, sweet Lena (Emily Watson). Sandler didn’t have anything on his résumé to suggest he’d have the depth for such a tormented character, except for one thing: His comedies often capitalized on his ability to go from calm to ultra-angry in seconds flat. But where that ability had been used for laughs in the past, Punch-Drunk Love channeled Barry’s rage and self-loathing into something incredibly touching but also frightening. Sandler had never been so vulnerable or poignant.
In subsequent years, the comedian has occasionally returned to serious fare, such as Spanglish or Reign Over Me. But none of those movies proved as comfortable a fit as Punch-Drunk Love — well, except for another film that’s coming up later on this list.
You Don’t Mess With the Zohan (2008)
By the mid-2000s, now one of Hollywood’s most bankable comedians, Sandler had mostly stopped playing zany characters, shifting to more-or-less ordinary guys. But then came this truly bizarre action-comedy about an elite Israeli commando named Zohan who always just wanted to be a hairdresser. And so, he does what anyone would do in his situation, which is to fake his own death, assume a new identity and move to New York City to pursue his dream. Unfortunately, his violent past comes looking for him.
At this stage of his career, Sandler could have made just about any movie and it would have been a hit, but although You Don’t Mess With the Zohan was another smash, it seems somewhat underrated in his canon of classics. Long in development, and co-written by Sandler and his buddies Robert Smigel and Judd Apatow, Zohan connected to his Jewish heritage in a way that makes the film’s eccentric humor unexpectedly personal.
“When I was a kid I always heard about the Israeli army,” he has said, “and you always heard about this tiny little country and how everyone around them wants them gone and every time somebody comes after them they take care of business. As a Jewish kid you were proud of that.” That said, Sandler’s principal inspiration was the hilarious juxtaposition of this assassin’s dangerous, high-octane life and his secret desire. “I always thought it was funny that he is a hairstylist and that someone would come in and make light of what he does and think there is no possible way he could kick his ass as much as he could.”
Zohan proved that Sandler was still willing to get weird in his mainstream comedies, relishing in the material’s sophomoric slapstick nuttiness. In the next few years, he’d occasionally try similarly oddball comedies like Jack and Jill, but Zohan’s wall-to-wall silliness was its own peak.
Uncut Gems (2019)
Before Uncut Gems, we all knew Sandler could do drama. But I’m not sure any of us were prepared for his performance as Howard Ratner, a small-time New York jeweler who’s drowning in debt because of his crippling gambling addiction. Fast-talking and morally slippery, Howard hopes to sell a precious opal so he can pay back a nasty loan shark, but there are plenty of twisty complications, pushing him into a desperate life-or-death situation.
Remarkably, Sandler seemed to access something deep inside him for the role, crafting a character who’s all sleazy swagger and self-delusion. It was revelatory, but it was also exciting: Uncut Gems’ crushing tension and reckless forward momentum made this the most thrilling film of Sandler’s career, and he was more than equal to the challenge.
“We were all kinda goin’ at it together,” Sandler recalled in 2020. “I think that (writer-directors Josh and Benny Safdie) have more energy than Howard. We were just thinking this movie night and day. … We kept it cookin’ the entire time.”
Uncut Gems was also the first time he got significant awards buzz, with his friend and Murder Mystery co-star Jennifer Aniston giving him a shout-out from the stage at the SAG Awards when she won for The Morning Show: “Oh, Adam Sandler, your performance is extraordinary and your magic is real, buddy.” A few years later when he got his first SAG nomination, for the basketball drama Hustle, it wasn’t that surprising. It took some people a while, but Sandler’s talent was finally being properly appreciated.
