10 of Adam Sandler's Best and Worst Movies

Script written by Mark Sammut

Top 10 Best and Worst Adam Sandler Movies

There are few stars more divisive than this guy! Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 10 Best and Worst Adam Sandler Movies.

For this list, we’ll be looking at Adam Sandler’s greatest films, along with his most terrible.

#5 WORST: “The Ridiculous 6” (2015)

This limp attempt at a Western comedy marked the dawn of a new era for Adam Sandler; "The Ridiculous 6" was the first movie to come out of the comedian's collaboration with Netflix. While arguably better shot than some of Happy Madison's lesser films, "The Ridiculous 6" finds Sandler at his most checked-out, with the actor bringing little to no energy to the lead role and rarely cracking anything resembling a joke. Not even the addition of Terry Crews can save "The Ridiculous 6"! The film meanders along in a way that makes its two hour runtime feel interminable. From one poorly conceived sketch about donkey feces to the next, plus ill-conceived caricatures and random baseball games, very little material lands.

#5 BEST: “The Wedding Singer” (1998)

After two movies that stressed Sandler's angry-man shtick, "The Wedding Singer" shifted focus to the comedian's softer side. Cast alongside the infallible Drew Barrymore, Sandler's Robbie Hart is genuinely kind and sympathetic, even if being left at the altar left the singer somewhat broken. As a rom-com, "The Wedding Singer" gets by on the chemistry between its two leads, while also using Sandler's trademark outbursts as part of the protagonist's growth rather than just a quick and identifiable gag. While Steve Buscemi might steal the biggest laugh in the movie, Sandler delivers an earnest and warm performance that has stood the test of time.

#4 WORST: “Bedtime Stories” (2008)

In "Bedtime Stories", Sandler stars as a handyman who tells stories to his niece and nephew that begin to affect real-life. It’s not the most aggressively terrible Adam Sandler film, but it represents many of the actor's worst traits. In a story that would have felt tired in 1988 let alone 2008, Sandler - as always - plays a passive-aggressive man-child who weasels his way into the role of a hero without much of the prerequisite character depth or sacrifice. "Bedtime Stories" saw Sandler trying his hand at a family picture, which might explain why the movie feels so neutered compared to the comedian's other projects.

#4 BEST: “Uncut Gems” (2019)

Given the right material, Adam Sandler can deliver one hell of a gripping performance, and "Uncut Gems" finds the actor at the height of his powers. The Safdie brothers' anxiety-inducing crime thriller casts Sandler as Howard, a jewelry store owner with a gambling addiction that’s left many people vying for his head. Delusionally optimistic and obnoxious yet likeable, Howard isn’t that far removed from many of Sandler's comedic personas. The difference is that "Uncut Gems" drops the character in a world that has consequences and does not reward faux-bravado. "Uncut Gems" is not the easiest of films to sit through, but it is one of Sandler's crowning achievements as an actor.

#3 WORST: “Grown Ups” (2010)

During the 2010s, quite a few of Sandler's films have felt like little more than an excuse to get the gang back together for a well-paid vacation. But the "Grown Ups" movies are the worst offenders. While the cast probably had a great time, none of that translates into the final product. What cinemagoers got is two movies that are devoid of tension, drive or any sense of rhythm. With talents like Chris Rock and Selma Hayek, "Grown Ups" is blessed with a solid cast but refuses to do anything with it. Adam Sandler's "Grown Ups" character can be summed up as "nice" or "good;" unfortunately, he doesn’t come anywhere close to "funny."

#3 BEST: “Happy Gilmore” (1996)

A quintessential Sandler flick that would encourage many of his subsequent characters, "Happy Gilmore" embodies the actor's trademark brand of comedic violence without constraints. As an explosive hockey player who ends up taking the golf world by storm, Happy is a truly strange beast of a personality, one who is pretty awful but still somehow endearing. Of course, partial credit for Happy’s hero status must go to Christopher McDonald's turn as the cartoonishly sinister main villain. "Happy Gilmore" is an unhinged force of a movie that - while not to everyone's tastes - played a crucial role in cementing Sandler as comedy royalty.

#2 WORST: “That's My Boy” (2012)

Branded with an R-Rating and co-starring another "SNL" alumni in Andy Samberg, "That's My Boy" should have been better than many of Adam Sandler's insomnia-curing later day vehicles. Even though Donny Berger is a more vigorous character than Sandler's typical popular outcasts, in general, "That's My Boy" is insufferable and lazily crude. It blatantly regurgitates the same tired punchlines without trying to deliver anything new besides just being a lot more vulgar. The exhausting humor alone is enough to sink "That's My Boy," but the film also tackles sensitive topics with all the nuance of, well, a bottom-of-the-barrel Happy Madison production.

#2 BEST: “Billy Madison” (1995)

Even after more than two decades of Sandler, "Billy Madison" still stands out as a refreshingly silly comedy that makes the best out of the actor's adolescent humor. Billy is an emotionally stunted and penguin-hallucinating man-child who must go back to school to inherit his father's company. Otherwise, it will go to the evil vice president. "Billy Madison" is one of Sandler's most surreal movies, one that distills the comedian's brand of entertainment to its purest and most unfiltered form. Like most of the comedian's earlier flicks, "Billy Madison" is a love-it or hate-it affair, but it does capture Sandler at his most honest and exuberant.

Before we unveil our top picks, here are a few honorable and dishonorable mentions.

WORST: “Pixels” (2015)

BEST: “The Meyerowitz Stories (New and Selected)” (2017)

WORST: “The Cobbler” (2015)

BEST: “The Waterboy” (1998)

WORST: “I Now Pronounce You Chuck & Larry” (2007)

BEST: “Big Daddy” (1999)

#1 WORST: “Jack and Jill” (2011)

"Jack and Jill" is a marvel to behold. The 2011 comedy - a phrase to be used lightly - is so completely incompetent, unabashedly grating, and insultingly formulaic that it seems to exist solely to elevate Sandler's other films by association. Sandler works double-duty as an executive with a nearly perfect life and his sister who ruins it. The star plays Jill as an unlikeable caricature whose comedic depth never rises above the level of crude fart dispenser and an annoying voice. Even with Al Pacino giving a bizarrely committed performance, "Jack and Jill" is an abomination on a scale seldom seen in cinema.

#1 BEST: “Punch-Drunk Love” (2002)

Even in the dumbest of comedies, Adam Sandler's characters usually have an element of tragedy and frustration to them. In Paul Thomas Anderson's "Punch-Drunk Love", however, these layers are brought to the forefront. Sandler's Barry is a lonely and beaten down man who sells novelty items, has seven of the worst siblings ever, and miraculously finds himself in a love story. Barry's many angry outbursts are not cathartic or done for laughs; they cumulatively serve as a cry for help that those around him choose to ignore or aggravate. "Punch-Drunk Love" is a film that could only have come to be with Adam Sandler in the lead role, and the world is better off for it.