Adam Sandler Movies Ranked

Adam Sandler has been headlining movies for decades now. The former "Saturday Night Live" cast member and head of Happy Madison Productions has proven to be one of the most enduring comedy lead actors of all time. Even after starring in a slew of movies that were mostly drubbed by critics and in some cases box office flops, Sandler's still recognized as a titan of comedic filmmaking. This man manages to keep himself in the pop culture zeitgeist and create new things that bring amusement to moviegoers all over the world.

Sandler's career as a leading man has spanned everything from some of the worst-reviewed comedies of all time to acclaimed dramas that broke new ground for what Sandler could accomplish as a performer. Ranking all of Sandler's movies (which here entails films he plays the lead role in) from worst to best, one can appreciate the sheer volume of his output and his recurring deviations from what would be considered his norm, even if one doesn't necessarily enjoy all the films. Plus, everyone's bound to have at least one of Sandler's goofy comedies that struck a chord with them, and it's always good to be reminded of those immature yet entertaining projects.

"Jack and Jill" was the perfect storm of bad movie elements. Not only was it an Adam Sandler comedy, but it was an Adam Sandler comedy where the actor plays two characters, one of whom is an over-the-top woman named Jill. Such a concept sounds like a recipe for gratingly broad comedy and, it turns out, that's just what the final film delivered. On top of that, "Jack and Jill" also bombarded moviegoers with product placement, racist gags, and a plethora of hollow celebrity cameos. Sure, the closing Al Pacino Dunkaccino commercial scene is so surreal you can't believe it actually exists, but it's not worth sitting through a movie this bad to get to.

With "Hot Rod," "Palm Springs," and "Popstar: Never Stop Never Stopping," Andy Samberg has starred in some truly impressive comedies, but his 2012 Adam Sandler vehicle "That's My Boy" is not one of those titles. One of Sandler's rare 21^st-century outings with an R-rating, "That's My Boy" fills the screen with lazy attempts at being provocative where other Sandler comedies pack the frame with schmaltzy sentimentality. All kinds of taboo subject matter, including incest and statutory rape, get brought up as cheap gags in "That's My Boy," but none of it's funny or saying anything interesting. Shock value comedy that's neither shocking nor amusing, "That's My Boy" is a blight on the careers of both Sandler and Samberg. At least its total failure made for an amusing punchline in a "Saturday Night Live" music video.

In 2015, Tom McCarthy's "Spotlight" hit theaters before going on to win the Academy Award for Best Picture. The same year, McCarthy directed Sandler in "The Cobbler," a high concept comedy whose jokes were stale and whose instances of poignancy came off as forced. In other words, this movie was as uncomfortable to watch as wearing a pair of shoes three sizes too small.

For his first decade or so as a leading man, Adam Sandler's PG-13 live-action comedies were guaranteed box office hits — well, almost all of them. The exception to this phenomenon was "Little Nicky," which failed to draw a crowd and for good reason. For one thing, of all the funny voices Sandler's used in his film career, the one he employs for the titular lead of "Little Nicky" may be his absolute worst. For another, the convoluted premise, involving the spawns of Satan, lacks the everyman aesthetic that attracts general moviegoers to Sandler's works. Oh, and "Little Nicky" is also about as funny as a funeral, which couldn't have helped either.

In the years since "I Now Pronounce You Chuck and Larry," there have been many strides made for the rights of queer individuals in the United States of America. However, this story about two male firefighters who forge a marriage for personal gain remains as terrible as it did back in 2007. Kevin James doesn't make a great case for why he because a Happy Madison leading man with his forgettable work here, and the attempts at sincere attitudes towards queerness are as strained as the tired gay panic jokes. Viewers will need to immediately watch something on par with "But I'm a Cheerleader" to wash out the repugnant taste of "I Now Pronounce You Chuck and Larry."

After working together on "50 First Dates," Adam Sandler and Drew Barrymore reunited for this comedy about two single parents who end up going on the same exotic African vacation together. What sounds like the set-up for a disposable sitcom is the basis for a movie that runs too long and can't wring as many funny situations out of its central set-up as it should. Worse, Sandler and Barrymore just don't have engaging chemistry here and the supporting cast is forgettable. "Blended" isn't the worst film ever, but its banal nature means it may be one of the most forgettable Sandler vehicles. At least the likes of "Jack and Jill" gave you horrendous moments you couldn't remove from your brain.

"Grown Ups" is the cinematic equivalent of tossing a bunch of things at the wall and seeing what sticks. In this case, a slew of comedians and famous faces were assembled for what amounts to glossy home video footage in the hopes of securing a consistently funny comedy. There's enough talented people on hand that a handful of gags do land, but for the most part, "Grown Ups" just isn't all that funny and mostly a reminder of how much better folks like Kevin James have been elsewhere. Sometimes, sheer quantity is not enough to make a movie hysterical.

Chris Rock and Adam Sandler reunited once again in 2018 for a middling wedding comedy called "The Week Of." Rock and Sandler have done plenty of funny movies over the years, but "The Week Of" isn't one of them thanks to its generic wedding-themed gags. There's also an overdose of sentimentality that just doesn't work with these characters. The only memorable part of the proceedings is Steve Buscemi showing up in an amusing supporting turn. Otherwise, this is one comedy you shouldn't RSVP to.

A remake of a 1970s Burt Reynolds movie, "The Longest Yard" saw Sandler playing some prison yard football. Despite featuring performers such as James Cromwell and William Fichtner in supporting roles, "The Longest Yard" can't rise above feeling like an obligatory remake. It's a film whose creative process seems to have began and ended with the concept of pairing Sandler up with the title of a familiar 1974 feature. The only truly notable part of the proceedings is, in the context of history, it did end up being one of the last appearances of Reynolds in a theatrically released live-action film. Aside from that trivia, "The Longest Yard" is a forgettable fumble.

Adam Sandler and a magical remote that can control time. That single sentence describes all of what "Click" is, save for a third-act detour into heavy emotion that's tied to Sandler's protagonist accidentally skipping over so much of his life. Neither the extreme schmaltz nor the derivative gags tied to the remote will prove memorable long after you stop watching "Click." One bright spot is Christopher Walken as the man responsible for bestowing Sandler's character with that remote. Unfortunately, this legendary performer isn't around nearly enough to make much of a difference and salvage "Click."

Adam Sandler in man-child mode gets saddled with an actual child to take care of in "Big Daddy." The results of such a premise are about what you'd expect, right down to the requisite sight of a young child spouting off profane dialogue and forced attempts at sentimentality. None of it reaches the depths of "Jack and Jill," but little of it proves altogether effective since director Dennis Dugan executes both the vulgarity and the poignancy with equal levels of noncommittal energy. However, it's worth noting that "Big Daddy" does have its fans, including Oscar-nominated director Paul Thomas Anderson. 

If you're of a certain age, several quotes from "The Waterboy" are likely imprinted on your brain, the same way other generations latched onto key moments from comedies like "Airplane!" and "Anchorman." However, a movie cannot get by on a few memorable comedic zingers alone, and Sandler's attempt at a wacky sports movie ends up overstaying its welcome even with a 90-minute runtime. Part of the problem is Sandler's character — yet another performance brought to life with an aggravating voice — while further holding the movie back is its rigid adherence to blandly executing formulaic storytelling. Some memorable pieces of dialogue can't keep "The Waterboy" from being less than the sum of its parts.

In the 2000s, Adam Sandler largely played everyday people who then got themselves into larger-than-life situations. In "You Don't Mess with the Zohan," Sandler eschewed that template to play Zohan, an Israeli counterterrorism agent who comes to the U.S. to cut and style hair. There's at least three tired gags for every successful laugh here and its approach to the Israeli-Palestinian conflict is, unsurprisingly, heavily problematic. However, the more high-concept nature of the proceedings at least makes "You Don't Mess with the Zohan" a touch more interesting than, say, "Grown Ups."

Perhaps it was aided by the fact that it came out during the COVID-19 pandemic, when everyone was desperate for any new movies, but "Hubie Halloween" is a better than average installment in the Adam Sandler comedy canon. The worst kind of cheap jokes, like farts, are kept to a minimum, the autumn Massachusetts backdrop is pretty look at, and a running gag involving T-shirts worn by June Squibb's character proves surprisingly amusing. Unfortunately, Sandler's titular character isn't all that funny, especially with his annoying voice. If only this protagonist had been fine-tuned, "Hubie Halloween" could have really been a comedic treat.

Upon its theatrical debut, "Billy Madison" wasn't just panned by critics; it was outright decimated by them, with Gene Siskel and Roger Ebert, for example, both severely disliking the project. It's not hard to see why, given that "Billy Madison," Sandler's first star vehicle after hitting the big time on "Saturday Night Live," is only intermittently amusing. The titular lead of "Billy Madison" may be somebody who has contempt for the rules, but the movie he inhabits is largely content to hit familiar narrative and comedic bits. 

On the plus side, the fact that it's a step up from other 21st-century Sandler fare, especially in terms of filmmaking ("Billy Madison" was shot on 35mm film, unlike the flat digital camerawork of modern Sandler works like "The Do-Over"), does make it easy to see why "Billy Madison" has developed its share of modern defenders.

"Funny People" doesn't entirely work like it should. For one thing, like all Judd Apatow directorial efforts, it runs too long and has a tendency to rely on shockingly conventional storytelling conceits for a supposedly "edgy" R-rated comedy. But Apatow does provide some surprisingly thoughtful moments throughout the production and his personal connections to leading men Adam Sandler and Seth Rogen lend a sincerity to those elements of poignancy. It's messy for sure, but "Funny People" is a welcome deviation from the norm in Sandler's comedy filmography.

"Happy Gilmore" isn't a total hole-in-one as a comedy, thanks to rampant product placement and certain juvenile gags missing the mark. But there's a reason even prestigious websites like Vulture have come around to praising this particular Sandler comedy in recent years. Juxtaposing Sandler's brash antics with the refined game of golf yields more laughs than one might expect, plus making the main character's impetus for engaging in a golf career — that he wants to help his grandma out financially — gives this one a better narrative thrust than most Sandler comedies. Throw in committed supporting performances from the likes of Christopher McDonald and Carl Weathers and "Happy Gilmore" becomes a surprisingly affable comedy.

The thought of Sandler portraying someone with a mental health issue, recovering from a tragedy connected to the September 11 attacks, sounds like a recipe for a disaster. Luckily, "Reign Over Me" is a drama, not a juvenile comedy. Pairing Sandler up with Don Cheadle, "Reign Over Me" does tend to dip its toes into schmaltzy waters, but Sandler lends welcome authenticity to his challenging role. He also has a believable rapport with Cheadle, which makes the complicated friendship that "Reign Over Me" chronicles all the more interesting to watch unfold.

Paul Thomas Anderson, the director of such weighty films as "The Master" and "There Will be Blood," apparently likes Adam Sandler comedies. His knowledge of this subgenre was put to good use on "Punch-Drunk Love," which was basically a dark version of such films. The basic premise could have easily been an upbeat Happy Madison production, but emphasizing the realism in the proceedings made Sandler's riveting performance disturbing rather than hysterical. It's a fascinating translation of a familiar formula, made all the more compelling by Anderson's masterful direction and a killer's row of supporting performances, including an unforgettable turn from Phillip Seymour Hoffman.