Whoopity doo!: The best and worst Adam Sandler movies

Adam Sandler as the lead in a romantic comedy? One where he’s actually kind of sweet and not a lunatic or a moron? In 1998, that was practically unheard of, but in “The Wedding Singer” he’s pretty perfect as Robbie Hart. It helps that he’s playing off Drew Barrymore as his romantic interest. They would run it back with “50 First Dates,” which wasn’t quite as successful. Maybe it needed more Billy Idol?

OK, the time for praising Sandler is over. We’re talking “Jack and Jill” now, and there is nothing good you can say about this movie. It’s arguably the worst thing Al Pacino has been a part of, and he’s in “The Devil’s Advocate!” Sandler’s dual-role performance is awful, especially when he plays Jill, one of the more grating characters ever committed to celluloid.

Somehow, this almost feels like cheating, because “Punch Drunk Love” isn’t your typical Sandler movie. It’s a Paul Thomas Anderson movie that Sandler stars in. It’s also pretty clearly the best movie that he’s even been in. After all, P.T. Anderson is one of our greatest living filmmakers, and he got a truly great performance out of Sandler that makes you wish he’d spend a little less time mugging in goofy costumes.

Hot take: “Big Daddy,” which came out between “The Waterboy” and “Little Nicky,” is a bad movie. Many will disagree, but basically everybody agrees that “Little Nicky” was a severe misstep. Sandler stars as the son of the devil, and this movie feels like a torture implement straight from the depths of hell. It’s profoundly unfunny and is basically Sandler at his worst.

This film is a remake of a Burt Reynolds vehicle about a group of inmates who take on the guards in a football game. The original is solid and so is the remake, which doesn’t try and reinvent the wheel. Now, is Sandler believable as a former NFL quarterback? That’s iffy, but the movie is just fine anyway.

“Grown Ups” is the movie that spawned the theory that Sandler just makes movies to hang with his friends and goof around. Also, he cast Salma Hayek as his wife. It’s wish fulfillment masquerading as a movie, and that makes it boring to watch even if it was possibly fun to film.

By the time he made “Click,” Sandler’s stardom was already on the wane thanks to some lackluster comedies. However, it’s actually a bit of a diamond in the rough in his filmography. The premise of a magical remote that controls time is silly, but there is a bit of heart, and some genuine insights about the march of time, at its core. Nobody should rush out to see it, but if it’s on TV, maybe consider checking it out.

The sequel to “Grown Ups” is more of the same. By writing multiple sentences about the film, we’ve arguably put more effort into discussing this movie than the people who made it put into producing it. At least Sandler probably had fun, and he got to give Shaquille O’Neal a cameo for some reason.

“Billy Madison” is dumb. It’s sophomoric. So much of it does not stand the test of time. On the other hand, a handful of bits and comedy set pieces are still genuinely laugh-out-loud funny. There are dozens of comedies that come out every year that fail to do that, so Sandler deserves some credit in his first real starring role for making that happen.

Like many men of a certain age, Andy Samberg grew up on Sandler’s comedies. He was probably happy to get to make a first with the Sandman. Unfortunately, the result is truly atrocious. Everything about this movie is a misstep, and the genuinely talented and funny Samberg is pulled down into the mire. Thankfully we will always have “Brooklyn Nine-Nine.”

Did we need three “Hotel Transylvania” movies? No, not really. One was enough. But that one, the first “Hotel Transylvania,” is actually a solid little animated family film. It’s kind of a spiritual successor to something like “The Munsters,” only with Sandler voicing Count Dracula and some of his other buddies adding in their voices as well.

If you think we’re just razzing on Sandler’s lazy post-2000 comedies, that is not the case. This was one of Sandler’s attempts to make something more serious and dramatic. Tom McCarthy, who made “Spotlight,” co-wrote and directed it. From this pairing we got a movie about Sandler as a man who can inhabit somebody else’s body by wearing their shoes. Seriously. It’s insane.

“The Waterboy” is the tipping point for Adam Sandler’s comedies. The characters started to get insanely broad, the strains started to show, and in time the whole concept would collapse in on itself. That being said, even with the ridiculous mannerisms of Bobby Boucher, there is some fun in this film. Watching Boucher tear it up on the football field can be delightful, and let us not forget national treasure Henry Winkler is in this movie. That alone earns it several points of merit.

Look, Sandler didn’t invent quasi-problematic film premises. However, “Just Go With It” is about Adam Sandler asking his employee Jennifer Aniston to pretend to be a woman he is divorcing so that he can sleep with Brooklyn Decker. That’s bad enough as it, but on top of that there’s nothing really funny in it.

Noah Baumbach tried to pull a trick out of P.T. Anderson’s playbook by casting Sandler in a bit of indie prestige fare. Though Baumbach has made some fine films alongside Greta Gerwig, left to his own devices he isn’t quite on Anderson’s level. However, this movie features Sandler, Dustin Hoffman, Emma Thompson and Ben Stiller. You can’t argue with a cast like that.

Damning with faint praise: “I Now Pronounce You Chuck and Larry” isn’t as bad as you might imagine a comedy about Sandler and Kevin James as straight men pretending to be a gay couple to be. They manage to avoid some of the casual homophobia and gay panic you fear. However, it’s just kind of blah and not funny, because while Sandler can act when he feels like it, James simply cannot.

“The Do-Over” is the kind of movie people feared when Sandler signed his Netflix deal. It’s him and his buddy David Spade making a bad action comedy together. If Spade isn’t paired with the late Chris Farley, he just simply can’t hack it on screen (and “Black Sheep” wasn’t really all that good, anyway). Even though you can just throw it on Netflix whenever you want, give it a hard pass.

Adam Sander’s Netflix deal has mostly churned out mediocrity and outright dreck, but “The Week Of” manages to rise above that. Sandler and his running buddy, Chris Rock, star as fathers navigating an upcoming wedding. It’s less crazy than most of Sandler’s recent comedies. People actually act like humans at times. This was a refreshing blast from the past in many ways and showed that Sandler still has it in him to make a decent comedy.

An animated film about Hanukkah, from the man who brought us the “Hanukkah Song,” could have been good. It wasn’t, though. The voice work is obnoxious — you can thank Sandler for that — and the animation is just unpleasant to look at. Certainly “Eight Crazy Nights” isn’t ready for the holiday film pantheon. It belongs with Jim Carrey’s “How the Grinch Stole Christmas” and failures of that ilk.

“Happy Gilmore” was the second Adam Sandler-starring vehicle, and it’s probably the silly, Sandler-esque comedy that holds up best. The actor stars as a failed hockey player who turns out to have a powerful drive off the golf tee, and he manages to join the PGA tour and find success. It’s an insane premise, but there are quite a few funny moments, including when Bob Barker beat up Happy at a golf event.

After a couple notable, quality performances, Sandler went back to his Netflix comedy well and his "a funny voice qualifies as a character, right?" schtick. "Hubie Halloween" is about an odd, Halloween-loving guy who...ends up trying to solve a kidnapping? Now, it's not the worst Sandler comedy, but it's definitely lackluster and utterly forgettable.

Part of what made "Hubie Halloween" feel so flat and uninspired? It came in the wake of perhaps Sandler's best acting work ever. "Uncut Gems" is an incredibly intense, claustrophobic drama from the Safdie Brothers, who specialize in movies of that ilk. Sandler plays Howard Ratner, a compulsive gambler who just can't quit the rush he gets, even as it threatens to destroy him. There was talk Sandler would get an Oscar nomination, and while that didn't happen, he did win Best Actor from the National Board of Review and the Independent Spirit Awards.

Once upon a time, Mel Brooks made the iconic comedy Western, "Blazing Saddles." Since then, most attempts to make a Western funny have flopped. "The Ridiculous 6" is a riff on "The Magnificent Seven," and it stars an eclectic bunch of actors which actually draws from outside Sandler's usual cronies (give or take a Rob Schneider). That doesn't make it any funnier, though.

Sandler loves basketball. He finally made a basketball film in 2022, but it isn't a comedy. Instead, "Hustle" is a drama about a burnt out veteran scout who stumbles upon a young player he thinks has star potential. Actual NBA players, and teams, are in the mix, which helps take "Hustle" to another level thanks to the authenticity.