The best Adam Sandler movies, ranked

A sort of hard-rock take on Dog Day Afternoon, in which a band of headbanging dunces take a radio station hostage and demand to have their demo played on the air, this ’90s relic has Sandler in a rare supporting role, stealing the show as the power-trio’s dopey drummer. (His bandmates are Brendan Fraser and Steve Buscemi. Pretty good cast, no?) Critics hated it, but it’s since found a worshipful audience – a trend that would come to define Sandler’s run throughout the decade.

The actor-comedian gets his answer to Casino Royale and his answer to Shampoo in this deeply silly comedy about an Israeli special forces soldier who follows his Paul Mitchell dream and becomes a hairdresser in New York. The romance with a Palestinian-American (Emmanuelle Chriqui) and the optimistic message of peace that ensues may not heal a troubled world, but there’s some pretty solid jokes and a commitment to the bit that delivers cinema’s first (and only) piranha-off.

This Judd Apatow tears-of-a-clown dramedy was the nail in the coffin for Madison 23, the production arm Sandler set up to give himself more weighty dramatic work. Audiences, it turned out, found the idea of him playing a legendary comedian who loses his desire to tell jokes in the face of terminal illness to be, well, a bit of a bummer. But while Funny People has its self-indulgent streak, Sandler’s willingness to send up his own public image as a Hollywood-minted movie star with a few dodgy comedies to his name is fun to behold and his hangdog charm fits the role to a tee.

Bogie and Bacall, Tom Hanks and Meg Ryan… Sandler and Barrymore? Six years after The Wedding Singer, the pair reunited for this silly-sweet romantic comedy about a career womaniser who falls in love with an amnesiac schoolteacher, and manages to tap into a similar broadly appealing chemistry. Lightning would not strike thrice with 2014’s Blended, unfortunately.   

As a big-time basketball fan, getting cast alongside a bunch of real-life ballers in this Netflix sports dramedy must’ve seemed like fantasy camp for Sandler, but he doesn’t treat the role as another vanity project. His every-schlub charm is in full effect as an NBA talent scout who has grown sick of the grind before the discovery of a young phenom (Spanish star Juancho Hernangómez) reignites his passion for the game. 

Fun fact: Sandler has played Dustin Hoffman’s son twice on screen. If you’ve only got time to witness one dose of fidgety, deeply awkward dad-son dynamics, skip 2014’s lamentable The Cobbler and head for the Jewish family squabbles of Noah Baumbach’s comedy-drama. Sandler is great as single dad Danny, moody but mostly well-intentioned and incredibly bemused by his bohemian family. If someone parachuted Billy Madison into the middle of The Royal Tenenbaums, it might look a bit like Sandler wrestling with the pain of his father’s casual neglect. A bit of a heart-breaker, all in all. 

If you’d suggested in the ’90s that Adam Sandler may win an Oscar one day, well, the title of a certain comedy album comes to mind. But collaborating with Paul Thomas Anderson has a way of shifting perceptions. For the director, his followup to Magnolia qualified as a toe-dip in the waters of romantic comedy. For Sandler, it was a stark departure, you have to wonder what Anderson saw that others to that point didn’t. As Barry Egan, a bathroom supply salesman with crippling social anxiety, Sandler turns the volume all the way down, save the occasional burst of rage. Whatever Anderson perceived in him, he was right: it’s an affecting yet still funny performance that still seems like an outlier even now.

If you weren’t a teenager in the ’90s, Sandler’s wilfully annoying onscreen presence is hard to feel much affection for, but the persona he began cultivating on Saturday Night Live and his comedy albums arguably reached its ideal form as a failed hockey player who brings his athletic goonery to the mannered world of golf. No wonder it’s getting a legacy sequel. Say it with us: ‘The price is wrong, bitch!’

Critics didn’t start taking Sandler seriously as an actor until he hooked up with Paul Thomas Anderson, but in this sweetly crowdpleasing romcom, he proved he could do something other than yell in silly voices. As a bemulleted ’80s rock frontman hopelessly in love with an already betrothed Drew Barrymore, he showed he could play a leading man worth rooting for, rather than simply laughing at.  

Adam Sandler has made plenty of movies that’ll make you cringe, for one reason or another, but none will have you hyperventilating into a paper bag like this feature-length panic attack from the Safdie brothers. Most of the time, when Sandler takes on a dramatic role, he plays it quiet and mumbly. As Howard Ratner, a Diamond District jeweler with severe risk addiction, he is every bit the obnoxious manchild he’s most famous for playing, except he hides his deep insecurities behind a conman’s perpetual grin. He pulls off a tough feat, making you tie your guts in knots over a character who’s not even worth all the stress.