Adam Sandler is responsible for a lot of iconic films — as well as a lot of iconic flops. With his production company, Happy Madison, Sandler has been acting in and producing films since 1999, to varying degrees of box office success. Money, however, definitely isn't everything when it comes to these screwball comedies.
While a lot of these films have aged pretty well, some of them have absolutely not, which can make a nostalgic rewatch turn sour pretty quickly.
Best: 'The Wedding Singer' (1998)
In this 80s themed movie, Adam Sandler plays the titular wedding singer, Robbie, who has to go back to work after being left at the altar and slowly falls in love with his new friend, a waitress named Julia (Drew Barrymore).
This was the first of three team-ups between Sandler and Barrymore and remains the absolute best. It's sweet, charming, has excellent side characters and comedy, and a love story that you truly root for. The soundtrack is also one of the best in any of Sandler's movies, with a lot of nostalgic hits including an excellent J. Geils Band cover as well as two original songs.
Worst: 'That’s My Boy' (2012)
That’s My Boy follows Sandler as an immature middle-aged man trying to reconnect with his similarly aged son to regain the fifteen minutes of fame that he had as a child (and also avoid prison after evading taxes).
This movie aged extremely poorly, and honestly wasn’t a good idea, to begin with. Sandler’s character is a victim of an abusive relationship with a teacher that resulted in a son (played by Andy Samberg, who went on to star alongside Sandler in the Hotel Transylvania franchise), which is presented by the text as an accomplishment rather than a horrifically traumatic assault. It is mishandled in every way.
Best: 'Happy Gilmore' (1996)
Maybe one of Sandler’s most iconic films, Happy Gilmore sees Sandler take the moniker of a hockey player who takes on a golf tour championship, using his slap-shot technique to win big and support his grandmother as she faces her home being repossessed.
There is a lot of fun to be had in revisiting Happy Gilmore, from Sandler’s classic over-the-top performance to the eccentric side characters that fill out the world around the story. The comedy holds up pretty well, and every other line is a well-known quote, which just goes to show that this film has a firm place in the comedy Hall of Fame.
Worst: 'Pixels' (2015)
This movie is all about retro games and the dudes that play them, following a group of middle-aged men who conquered the world of arcade games in their youth and have to use those honed skills to save the world from an alien invasion.
Pixels is a whole lot of “back in my day” and not much else. The story lacks any kind of substance, and while the visual effects are good it doesn't make up for the condescending tone that the movie poses. There's also a side plot where Josh Gad meets a video game girl he's been obsessed with since childhood, who eventually their sidekick Q*bert transforms into so that Gad's character can have a prize — which, needless to say, is wildly sexist.
Best: 'Click' (2006)
Click takes the concept of a "universal remote control" (very prevalent in the 2000s) to the absolute extreme when Sandler's character uses it to change the course of his life, before realizing that maybe it wasn't such a good idea to mess with time so frivolously.
The perspective a lot of people have of this film is that it was the first Adam Sandler movie to make them cry. In retrospect, it is anything but emotional, yet it's extremely fun to rewatch: you realize that this man doesn't use his new power effectively, but the movie continues to punish him even when he learns his lesson. Between the ridiculously on-the-nose plot and dialogue, the emotionally manipulative and melodramatic score, and the memorable performances from an excellent supporting cast, Click is the epitome of "so bad it's good".
Worst: 'I Now Pronounce You Chuck and Larry' (2007)
To ensure his children’s future, Larry (Kevin James) enlists his best friend and fellow firefighter Chuck (Sandler) to pretend to be a couple and file for domestic partnership, so he can receive benefits via insurance fraud and make sure those funds make it to his family.
Unsurprisingly, this is one of the most homophobic movies ever made. Chuck and Larry are just gay jokes, gay jokes about prison, gay jokes aimed at children, misogyny and sexual assault, arguably Rob Schneider's most racist character to date, and to top it off, a poorly aged shout-out to Rudy Giuliani (of Borat 2 fame). While it half-heartedly tries to send a message about acceptance by the end, the damage is well and truly done by that point.
Best: 'Hubie Halloween' (2020)
In a return to form for Sandler, Hubie Halloween follows Hubie Dubois (Sandler) as he tries to solve the mystery of who is kidnapping citizens in his town, despite the objections of the police and the disdain he receives from everyone around him.
Hubie is lots of fun! Sandler’s performance is very silly in a way that is reminiscent of his early work, and June Squibb co-stars as Hubie’s mother with delightful charm (and excellent wardrobe). There are tons of cameos in this movie, from both celebrities and previous Sandler characters — adding fuel to the fire of the long theorized Sandlerverse. It’s a joyful ride with a lot of physical comedy, ready to be watched by fans every Halloween.
Worst: '50 First Dates' (2004)
The second of the Sandler and Barrymore team-ups, 50 First Dates follows Sandler as Henry, a playboy veterinarian living in Hawaii who falls for a girl he meets in a diner one day, before finding out she has short-term memory loss from a previous accident. Lucy, played by actress-turned-talk show host Drew Barrymore, relives the same day over and over again and has no memory of every meeting Henry, despite his best efforts to implant himself in her brain.
This movie is universally beloved as a romantic comedy, but retrospectively it's about the manipulation of an extremely vulnerable woman. While it comes across as protective from the family, giving the audience pause to think about the morality of their actions, with Henry this is not the case. He lies to her, learns information about her and uses it to his advantage, and constantly ignores both her and her family’s boundaries, which definitely detracts from the romantic side of things.
Best: 'Jack and Jill' (2011)
Jumping onto the multiple-role film for the first time, Sandler presents Jack and Jill as a zany comedy about twins who reconnect over the holidays.
Jack and Jill is pretty widely agreed to be Adam Sandler’s worst film, and that is the very thing that makes it so good to rewatch. Sure, it’s not his best, but the preceding reputation of this movie to be awful makes way for it to be surprisingly entertaining in contrast. It’s got a lot of great jokes and bits, Al Pacino is fun, and there’s a small appearance from Ruben Rabasa, the breakout star of Tim Robinson’s I Think You Should Leave. All in all, it’s a fun rewatch if you turn off your brain and let the ridiculousness of it wash over you.
Worst: 'You Don’t Mess With the Zohan' (2008)
Israeli soldier Zohan Dvir (Sandler) fakes his death and moves to the big city to pursue his hairdressing dreams, before being dragged into a conflict in New York City itself.
There is a lot to unpack in Zohan. The film frames itself around the Israeli-Palestinian conflict, a topic it is not at all equipped to handle with any kind of tact and that uses an almost entirely white cast to portray. The absurdist physical comedy doesn't work in this context and is used so sparingly over the almost two-hour runtime that it just feels out of place. At best, this movie is too long and uneventful, and at worst it's extremely offensive.