Where Did Adam Sandler Go Wrong?

I grew up thinking Happy Gilmore was the funniest movie I’d ever seen. I must have been five or six when my dad first popped it in the VHS player, and, in my ignorant kindergarten brain, that ridiculous golf comedy was everything. Despite a decent amount of raunch and cussing, I was allowed to rewind and replay as much as my little heart desired. By 1997, that tape had surely seen better days. I thought Adam Sandler was downright hysterical — a loon for the everyman. A comedic god among all men. And he very well might have been for a brief, brief moment in time, but then something went really wrong.

Out today is part-live-action, part-computer animated action comedy Pixels, starring Sandler, Kevin James, Josh Gad, Peter Dinklage, and Michelle Monaghan as alien-fighting arcade gamers. The verdict seems to already be in (re: it stinks), reaffirming yet again that the one-time funny man hasn’t starred in an acclaimed comedy in about fifteen years. No way, you say? I contest that Sandler’s last solid role, honest to goodness funny was Sonny Koufax in Big Daddy, which came out in 1999.

During his successful five-year stint on SNL, Sandler starred in Dan Aykroyd’s Coneheads, followed by Airheads, Nora Ephron’s Mixed Nuts, and Billy Madison — another movie I find myself absent-mindedly quoting at least once a day. Then came Happy Gilmore. Between Happy Gilmore and The Wedding Singer, however, was Bulletproof, a crapshoot starring Sandler and Damon Wayans as common crooks. “It’s okay,” Sandler fans thought, “Just a hiccup, right? Plenty of great comedians have starred in something unwatchable.” Then The Wedding Singer happened and we were given the go-to film for all syndicated networks and plane rides for years to come. After that, Sandler revisited the comedic skill that made him famous in The Waterboy, got uncomfortably weird in Little Nicky, and then shocked us all by starring in Paul Thomas Anderson’s Punch-Drunk Love — an dramatic acting feat for the comedian overshadowed by the fact it’s PTA’s most lackluster endeavor to date. After tapping into his dramatic side, Sandler starred in Mr. Deeds and, for retrospective purposes, that seems to be where it all went downhill.

Punch-Drunk Love was the best transition Sandler could have made at that point in his career, had he only stuck to it. He was phenomenal as Barry Egan, a down-on-his-luck novelty item salesman who’s relentlessly abused by all of the women in his life until he meets The One (played by a lovely Emily Watson). He was poignant, genuine, heart-breaking, and most of all, funny in the kookiest way that made us fall in love with him in the first place. Some comedians transition into drama so smoothly and believably that the audience hardly notices. Sandler could have been one of those comedians, yet like all of his characters, he just refuses to grow up, inevitably retreating back to man-child tendencies.

Punch-Drunk Love was a career-boosting opportunity for Sandler, yet the film came and went in the eyes of Sandler fans, because that same year, the stupidity of Mr. Deeds and its redundant humor overshadowed it. There’s nothing wrong with making movies with your pals — if you have the money and time, more power to you. Lord knows Rob Schneider and Kevin James aren’t doing much else these days. But there comes a point when you wonder if he’s aware that comedy has evolved since his peak or of the kinds of projects piling up on his IMDb page. It’s not looking too hot.

As someone who grew up with Billy, Happy, and Scuba Steve; I’d love to see a legitimate Sandler comeback. We got a taste of it a few years ago with Judd Apatow-backed Funny People, in which Sandler played a cancer-ridden dramatized version of himself, forced to reconcile with his bitterness. But the ongoing stagnancy caused by middle-of-the-road indies like Jason Reitman’s Men, Women & Children and supernatural dramedy The Cobbler, and now, the imminent blockbuster dud Pixels, still makes it an ongoing wish for fans who grew up laughing with him, not at him.

A previous version of this piece was published here last September. 

Like what you see? Follow Decider on Facebook and Twitter to join the conversation, and sign up for our email newsletters to be the first to know about streaming movies and TV news!

Photos: Paramount/Everett Collection