Adam Sandler went from Saturday Night Live cast member to a movie mogul in his own right, but how do his films stack up? Delivering laughs and entertainment throughout his career, the actor and filmmaker is perhaps best known for slapstick comedy and rude humor, but Sandler has presented a wide range that extends beyond typical expectations of him. In fact, some of his finest work comes in more dramatic roles, even when they aren't as popular in box office terms.
Sandler continues to cater to both sides of his talents with him regularly turning out both the comedies that made him famous and more risk-taking roles. While many of his films were successes despite criticism, some have certainly held up better than others. There is a lot of nostalgia surrounding Sandler movies, particularly entries like Happy Gilmore and Billy Madison, but his newer films, though similar to the older ones, have been panned and ridiculed, even by his fans.
44 Going Overboard (1989)
Sandler's first major starring role was in Going Overboard and it was not a great start. Sandler plays an aspiring comedian who takes a low-level job aboard a cruise ship in the hopes of getting to be the cruise comedian. The film is decidedly independent and rough around the edges. The rhythm is jarring, and its use of fourth-wall breaks and quick cuts create a disorienting sense of mayhem. Sandler's charm is possible to see even with the weak material but thankfully his career only went up from here.
43 Jack And Jill (2011)
From Eddie Murphy to Robin Williams, many great comedic actors have attempted dressing up as a woman for laughs and it is always hit-or-miss. Jack and Jill is a decided miss with Sandler playing brother and sister in this uninspired comedy. A thin plot, crude, base humor, and limited comedy that did not keep up with modern sensibilities led to Jack and Jill earning dismal reviews. It also has the distinction of being the first movie in the history of the Razzie Awards to win every category it was nominated in.
42 The Do-Over (2016)
The Do-Over delivers a solid set-up with two old friends, Max (Sandler) and Charlie (David Spade), who run into each other at a high school reunion. Charlie is dissatisfied with his life, but seeing Max brings him joy, and so Max makes the brash decision to fake their deaths so they can start anew in Puerto Rico. The Do-Over starts to give out narratively somewhere in act two, and the tone is increasingly confused and muddled. Sandler and Spade are fun together but the movie loses steam quickly.
41 Pixels (2015)
The greatest disappointment about Pixels is that it's a worthy premise executed poorly. The movie follows an alien invasion with the extraterrestrial attackers taking inspiration from '80s video games which leads to Sandler and a band of arcade champions being called upon to save the day. The idea was sound—even exciting—but a visual grandeur and a healthy dose of 1980s nostalgia did not manage to pull Pixels out of the mire. Despite talented actors like Peter Dinklage, Sean Bean, and Brian Cox appearing, the movie failed to have much fun with all its potential.
40 The Ridiculous 6 (2015)
Sandler and his band of usual costars stepping into a Western comedy was another solid idea with poor execution. The Ridiculous 6 follows a ragtag collection of men, all sons of an outlaw who band together to find their long-lost father. The Ridiculous 6 cast of characters is entertaining enough but the humor feels especially lazy. Sandler also makes the strange decision to play his character as a stoic hero, which is not fun at all. One highlight featuring John Turturro as Abner Doubleday teaching the band of brothers about his new game of baseball is hilarious, though.
39 That's My Boy (2012)
As Donny Berger, Sandler reverts into his usual man-child ways in this film about Donny's grown son Todd (Andy Samberg) getting married. With That's My Boy, however, the film earns a hard-R rating, a departure from Sandler's PG-13 home base. Sandler seems to revel in the freedom the rating affords him, diving deeper into crass exploitation and debauchery. Sadly, the movie misuses Sandler's costar as Samberg is made to be a dull straight man to Sandler's antics. It would have been far more enjoyable seeing the SNL alums share the zaniness. The movie resulted in one of the worst financial bombs of Sandler's career.
38 I Now Pronounce You Chuck And Larry (2007)
Sandler and Kevin James team up in I Now Pronounce You Chuck and Larry as firefighters who pose as a gay couple to get the benefits. With a draft of the script written by Oscar-winners Alexander Payne and Jim Taylor, there was perhaps a good version of this story lost out there somewhere. Though the movie attempts a message of acceptance and inclusion in the end, it was deemed offensive by many, not only for its depiction of the gay community but also Rob Schneider's horribly inappropriate cameo as an Asian minister.
37 Grown Ups 2 (2013)
Sandler and his famous friends reunited for the buddy comedy sequel Grown Ups 2 and didn't find anything interesting to say the second time around. Those who enjoyed seeing the crew together the first time might have fun with this reunion which repeats the endless fart jokes and crude humor. However, like the first movie, it feels like a waste of having so many funny people assembled to do so little.
36 The Cobbler (2014)
This 2015 fantasy comedy The Cobbler takes the notion of walking a mile in someone else's shoes and runs with it. The premise is interesting: a shoe repairman suddenly gains the power to appear as other people when he dons their footwear. There is of course the silly "what if" fantasy that alights a bit of imagination in viewers, but it falters in trying to take something sincere and squish it into a blockbuster. It is one of the rare instances of Sandler's more dramatic fare feeling like a total miss.
35 The Week Of (2018)
Ever since appearing on SNL together, Sandler and Chris Rock have been close friends and frequent costars. The Week Of sets them up as two fathers leading up to the wedding of their respective children. The major problem of this wedding comedy is pacing, in that, like many of his films, Sandler repeats jokes and punchlines to the point that they become background noise. Time that should have been given to Rock went to unfunny side characters, and what might have been a heartfelt story turns into a surprisingly boring Sandler project.
34 Bulletproof (1996)
This obscure buddy action movie is a decent albeit forgettable entry into the genre. Bulletproof stars Damon Wayans as an undercover cop who must reunite with the criminal he betrayed (Sandler) who is now a witness to a criminal conspiracy. This comedy crime movie from 1996 received mixed to negative reviews. On the one hand, it was chaotic, violent, and unoriginal, but it is also tempered with genuine humor. Sandler and Wayans have fun chemistry and there is even some entertaining action to get audiences past the thin story.
33 Blended (2014)
Blended was an honest attempt to recapture the magical chemistry Drew Barrymore and Sandler had found in their previous two romantic comedies. There is something to be said of its tonal consistency. Where it perhaps doesn't shine in story or its utilization of Barrymore's undeniable charm, it manages to focus on the theme of putting things together once broken. The emotionality doesn't feel shoehorned in at the last minute, nor is it drenched in false sentimentality. If anything Blended makes the case for Barrymore and Sandler need to reunite for another movie.
32 Bedtime Stories (2008)
Bedtime Stories is Sandler's first foray into a family-friendly movie with not entirely successful results. Sandler plays a man whose bedtime stories to his niece and nephew start coming true. This fantasy comedy is another Sandler film an execution that doesn't quite live up to its premise. Nevertheless, Bedtime Stories is a perfectly sweet children's tale filled to the brim with surprising and enchanting visual effects and an easy, uncomplicated storyline that is perfectly sound if not memorable.
31 Grown Ups (2010)
The gift that Grown Ups offers is in its relaxed, easy pacing, a pleasant departure from a lot of Sandler fare. Its biggest problem is not in slapstick humor or overblown stereotypes, but in its bloated cast. There is a hefty amount of talent, but Maya Rudolph, Maria Bello, and Chris Rock are underutilized due to runtime. The overall tone, however, is a good-natured one, and it permeates the film. There is a lot of affection that comes through the screen, and it makes for a memorable foray into the meaning of friendship. Perhaps a possible Grown Ups 3 can fully take advantage of the star-studded cast.
30 Men, Women, & Children (2014)
Jason Reitman's 2014 film Men, Women & Children examines fears faced by many modern parents: how is technology affecting them? While the children (or teenagers, rather), are indeed drudging through technological doldrums, the parents also find themselves addicted to the blue light. The intertwining stories are reminiscent of Babel or the divisive Cloud Atlas, but much less epic in scope. The film is nothing novel, but Sandler's performance is one of couched decency mingled with a nascent increase in proclivities that paint the portrait of a good person whose reliance on instant gratification is feeding his demons.
29 Sandy Wexler (2017)
Sandler plays one of his most likable characters, the titular kind but unsuccessful Hollywood manager, in Sandy Wexler. The film is punctuated with a Greek chorus of beloved celebrities sharing their recollections of Sandy and his ardent devotion to the people he represented. Within the awkward pacing and slow crawl of this movie is a fairly decent dramedy with an interesting story and an even more interesting lead character. Sandler is perfectly suited to Sandy, whose arrested development seems to mirror the way Sandler typically portrays his characters, but in Sandy, it's bittersweet and natural.
28 Hubie Halloween (2020)
Hubie Halloween sees Sandler play another man-child, but this time he's more sincere and genuine than an obnoxious frat boy. The self-referential humor abounds in this one, with Sandler favorites like Buscemi and Schneider popping up. Hubie doesn't seem to give up or collapse into depression despite all the abuse he gets from the town and finds value in himself and what he does. The genuine sweetness found in The Waterboy is regained, even if the laughs aren't as big this time around. If nothing else, it makes for a solid non-horror Halloween treat.
27 Eight Crazy Nights (2002)
Sandler's animated holiday movie was released in 2002 and despite an array of tawdry scatological gags and vulgarity replete with a dose of vitriol, Eight Crazy Nights does have something to say. Sandler's character Davey is experiencing difficulty connecting with his Jewish identity. He is slovenly and drunk, unable to find healthy coping mechanisms to deal with neurosis and antisocial habits. Being made to work for the basketball team allows him to focus outwardly, and even though the raunchy tone of the movie isn't quite waylaid by the almost begrudging addition of a happy ending, Eight Crazy Nights is not devoid of a message.
26 Little Nicky (2000)
Little Nicky's premise had a lot of potential: the devil's son finding his way on Earth after a lifetime in hell was ripe for all manner of visual gags and old-world references (including a plot quite similar to King Lear). The movie's main detriment seems to be Sandler's choice to play Nicky as a sort of infant grotesque with a sickly prince hairdo and a slanted, wet lisp. Had he played Nicky straight, it would have been interesting to see where the film had gone. But there are still laughs to be had and Little Nicky's cameos, including Quentin Tarantino, Reese Witherspoon, and Rodney Dangerfield elevate the comedy.
25 Just Go With It (2011)
Sandler teamed with Jennifer Aniston for the first time in Just Go With It, a comedy in which Sandler recruits Aniston and her children to pose as his ex-wife and kids to impress his new girlfriend. Had the movie committed to the despicable nature of Sandler's character it might have been more fun. Instead, it has to coast off of the charm and chemistry of the two leads, which is admittedly very solid.