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 .

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 dres 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.