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Adam Sandler Movies Ranked

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.

39. Going Overboard

Never heard of this Adam Sandler comedy? You’re not alone. “Going Overboard” was released in 1989, before Sandler was even hired to work on “Saturday Night Live,” let alone before the days of “Happy Gilmore.” It registered so little of an impact that there aren’t any reported box office figures for the film. There’s a reason for that: “Going Overboard” is sloppily-assembled fare even by the standards of Sandler comedies, with little in the way of energy or creativity in its filmmaking. The only saving grace of this feature is that many of its cast members at least went on to lucrative careers, including Billy Bob Thornton and future “Phineas and Ferb” creator Dan Povenmire.

38. Jack and Jill

“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.

37. Bulletproof

Just after Sandler established his credibility as a leading man with “Happy Gilmore” and “Billy Madison,” the “Saturday Night Live” alum headlined the action-comedy “Bulletproof.” It’s a wonder this title didn’t derail his leading man career, considering just how poorly it turned out. Special criticism was directed at the lack of chemistry between Sandler and co-star Damon Wayans, a critical flaw for what’s supposed to be a buddy cop movie. One of Sandler’s earliest star vehicles, “Bulletproof” is also one of the most listless features in the actor’s filmography.

36. That's My Boy

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 21st-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.

35. The Ridiculous 6

With “The Ridiculous 6,” Sandler ventured into new territory by headlining a movie made for a streaming service (in this case, Netflix). Unfortunately, the film was extremely familiar in basically every other way, a Western that attempted to be wacky but mostly just came off as desperate for laughs. The worst part of the production was how little chemistry the members of the titular group had with each other. With actors like Taylor Lautner and Rob Schneider failing to play amusingly off each other, Sandler’s first Netflix movie was a wild, wild bust.

34. The Cobbler

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.

33. The Do-Over

Reportedly, Adam Sandler turned down the lead role of “Knight and Day” because he was uncomfortable with the idea of playing a character who wielded a firearm. He apparently got over that trepidation when it came time for the 2016 comedy “The Do-Over,” where he’s the gun-toting guy that David Spade’s protagonist idolizes. There’s little to recommend and plenty to avoid in this terrible comedy, with the biggest victim of the proceedings being Paula Patton as the project’s female lead. “The Do-Over” concludes with Spade just beating Patton up in a moment meant to elicit cheers. Patton deserves better roles than this and moviegoers deserve better comedies than “The Do-Over.”

32. Little Nicky

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.

31. Eight Crazy Nights

Adam Sandler’s first foray into feature-length animation was “Eight Crazy Nights,” which did not make the best case for Sandler regularly exploring this medium of storytelling. What’s especially strange about this cartoon Hanukkah comedy is how it doesn’t take much advantage of any unique comedic opportunities present in either its central holiday or by being an animated film. Instead, it’s a lazily assembled work that often feels more like a commercial for various brands than a movie. If the producers thought the “shock” of seeing generic bathroom humor exist in a hand-drawn animated cartoon could carry this movie to being a hit, they were mistaken.

30. I Now Pronounce You Chuck and Larry

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.”

29. Grown Ups 2

In 2013, Adam Sandler and his buddies once again hung out and partied and then filmed the results, though this time the project was entitled “Grown Ups 2.” Rob Schneider may have been absent this go-around, but otherwise, “Grown Ups 2” was more of the same. Fat jokes, bathroom humor, obvious pop culture references, they’re all here and none of it’s amusing. It also continues to be puzzling how the four leads of the “Grown Ups” movies are real-life friends yet have so little chemistry together on-screen. The only entertainment to be gleaned from “Grown Ups 2” is pondering how on Earth Salma Hayek was coerced to do not one but two of these movies.

28. Blended

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.

27. Pixels

Video game movies are usually bad. Adam Sandler comedies are also typically subpar. An Adam Sandler comedy centered on vintage video game characters was probably destined to be awful. But “Pixels” proved especially anemic, thanks to a bunch of especially uninspired gags and director Chris Columbus’s equally unimaginative approach to filming big VFX-heavy action sequences. “Pixels” ended up as one of those movies that was just as bad on screen as it sounded on paper.

26. Grown Ups

“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.

25. Just Go With It

“Just Go With It” is supposedly a romantic comedy, but where’s the romance or the comedy? The story here is full of schemes and gratuitous male-gazey camerawork that ogles Brooklyn Decker. However, it’s notably short on laughs despite lead performers Adam Sandler and Jennifer Aniston having flashes of decent comedic chemistry with one another. Nick Swardson being on hand as an obnoxious comic relief sidekick just makes things extra hard to endure. Perhaps the most notable part of “Just Go With It” is that it actually involves a brief cameo from Nicole Kidman because, well, just go with it.

24. The Week Of

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.

23. Bedtime Stories

Adam Sandler and family-friendly Disney entertainment crossed paths with “Bedtime Stories,” which fixated on Sandler as a guy who finds that the bedtime stories he tells his nephews keep coming true in some form. Many big-screen comedians (like Robin Williams or Ben Stiller) have also worked well as family movie headliners. Sandler is not one of those comedians, as he doesn’t prove very interesting in his role here. The story itself, meanwhile, is never as fun or as creative as it should be, and there’s too many wasted opportunities for actual entertainment here to count. Grounding “Bedtime Stories” in the real world proves to be a fatal flaw, as does a dearth of laughs.

22. The Longest Yard

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.

21. Mr. Deeds

There aren’t many filmmakers or actors that would be properly up to the task of remaking a classic film by Frank Capra. Adam Sandler and company are certainly towards the bottom of the pack of artists who should even attempt a satisfying redo of a Capra film. A re-imagining of the 1936 film “Mr. Deeds Goes to Town,” “Mr. Deeds” doesn’t get many successful jokes out of the concept of Adam Sandler playing an everyday guy who suddenly gets saddled with elaborate riches. Even if there wasn’t a superior classic comedy to compare it to, “Mr. Deeds” would still register as underwhelming.

20. Click

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.”

19. Sandy Wexler

The strangest part about Adam Sandler’s comedies is how long they are. You’d think his juvenile efforts would never run over 80 minutes. Instead, many of them exceed over 100 minutes, including the 137-minute long “Sandy Wexler.” Despite such a hefty length, this 2017 showbiz satire features little to remember beyond a deluge of 1990s pop culture cameos and Sandler’s grating voice for the titular lead. Worst of all, this particular Sandler vehicle opted to drag in Jennifer Hudson and her beautiful voice. Even for someone who was in “Cats,” Hudson deserves better than “Sandy Wexler.”

18. Big Daddy

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. 

17. Murder Mystery

Adam Sandler and Jennifer Aniston reunited on Netflix for the comedy “Murder Mystery,” whose premise should be self-evident by its title. This comedy would’ve been average by any standards, but coming out the same year as “Knives Out” only reinforced that this was a meager take on the murder mystery comedy genre. At least Sandler and Aniston have passable chemistry, while the supporting cast largely eschews Sandler’s usual collection of Happy Madison regulars in favor of fresher faces, like Luke Evans and John Kani. Those details lend a layer of distinctiveness, albeit a thin one, to “Murder Mystery,” one of Sandler’s better forays into Netflix comedies.

16. The Waterboy

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.

15. 50 First Dates

One of Adam Sandler’s more well-regarded romantic comedies, “50 First Dates” partnered up this funnyman with Drew Barrymore for the second time in a high-concept comedy involving a woman who wakes up every day with total amnesia. The unique possibilities of this premise got diluted by hackneyed slapstick humor and an odd tendency to dilute the agency of Barrymore’s character. There’s a touch more effective tender sweetness here than in other Sandler vehicles, but otherwise, “50 First Dates” is one movie you can skip out on.

14. You Don't Mess With the Zohan

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.”

13. Hotel Transylvania 2

The high-concept premise of “Hotel Transylvania 2,” concerning a hotel for monsters, would seem to offer up limitless possibilities for gags and storylines. So it’s puzzling to see “Hotel Transylvania 2” center itself on generic gags like overly-safe playgrounds or tense interactions with one’s in-laws. Those could appear in any animated movie; why waste them in such a unique backdrop? These grounded gags also don’t play to the franchise’s best strengths, which are the zany animation and character designs. When the storyline of “Hotel Transylvania 2” does play into those qualities, it regains some footing, though it still can’t help but avoid being the weakest entry in the series.

12. Hubie Halloween

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.

11. Hotel Transylvania

It’s strange to consider that it took nearly two decades into his career as a leading man before Adam Sandler starred in an animated family movie. The time finally came with 2012’s “Hotel Transylvania,” a movie that allowed Sandler and several regular actors from his live-action movies to inhabit the roles of various famous monsters. The film itself is a standard kid’s movie in many ways, though at least it’s more successfully humorous than the worst live-action Sandler fare. The most exciting flourishes emerge thanks to the most stylized aspects of the animation, although there aren’t quite enough of them to make Sandler’s inaugural run in the domain of animated all-ages fare truly exceptional.

10. Billy Madison

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.

9. Spanglish

In his time as a filmmaker, James L. Brooks has directed some of the most acclaimed comedy-dramas of all-time, including “Terms of Endearment” and “Broadcast News.” His 2004 effort “Spanglish” is not one of those movies. The film does have its moments, including a welcome turn from Sandler in a more restrained mode as the story’s male lead. If “Spanglish” struggled to balance its comedic and sentimental impulses, at least Sandler’s performance provided some consistent quality in the project. A shame such a turn couldn’t have found a home in a better Brooks project.

8. Funny People

“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.

7. Hotel Transylvania 3: Summer Vacation

With “Hotel Transylvania 3: Summer Vacation,” director Genndy Tartakovsky cuts loose and brings this franchise’s computer animation closer than ever to the fluid zany style of hand-drawn animation. As a result, some of the most inventive gags in the entire “Hotel Transylvania” series pop up here. Sandler’s voice acting chops as Dracula still aren’t as lively as they could be, but with a greater emphasis on sight gags and visual humor, “Summer Vacation” doesn’t need Sandler to be in top vocal form. The cartoony imagery is the real star of the show here and helps inform the creative peak of the “Hotel Transylvania” saga.

6. Happy Gilmore

“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.

5. The Wedding Singer

Sandler’s first foray into mixing childish comedy antics with romance, “The Wedding Singer” proved surprisingly successful in spite of some serious issues with its tone. Part of that was pairing Adam Sandler up with Drew Barrymore for the first time: the duo have such solid chemistry in their scenes together that it becomes easy to see why they’d reunite regularly in the years to come. The A.V. Club also astutely pointed out that the sincerity in the actors’ rapport, as well as in Sandler’s protagonist, also helps make “The Wedding Singer” work as well as it does. What a welcome departure from later Sandler vehicles, which largely leaned on mean-spirited humor.

4. Reign Over Me

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.

3. The Meyerowitz Stories

Adam Sandler returned to dramatic acting for the first time in a decade for “The Meyerowitz Stories,” a 2017 Noah Baumbach feature that brought out the best in the actor. Rather than hamming it up with an obnoxious voice, Sandler conveyed a down-to-earth quality in portraying one of the key members of the titular Meyerowitz family. Though he’s good throughout, including in his chemistry with co-stars Ben Stiller and Dustin Hoffman, Sandler proves especially poignant in a scene depicting his character belting out a tune with his fictional daughter on a piano. Rather than conjuring up memories of Opera Man, this musical moment sees Sandler crafting a totally new character and a distinct sense of pathos.

2. Punch-Drunk Love

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.

1. Uncut Gems

He’s not the only successful part of “Uncut Gems,” but this Josh and Benny Safdie directorial effort could not exist without Adam Sandler’s lead performance as Howard. Why else would so many of his lines from this movie have become ubiquitous internet memes if Sandler didn’t deliver something special here? The actor is pitch-perfect in capturing the propulsive desperation that drives and defines the movie’s sweaty, anxiety-laden atmosphere. With a fascinating turn that reaffirms Sandler’s chops at darker dramatic performances, Sandler is the compellingly dark heart of “Uncut Gems” that you can’t look away from. Even better, the movie he inhabits has countless other outstanding qualities even when divorced from Sandler’s performance.

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