10 Best Adam Sandler Movies

10 Best Adam Sandler Movies
10 Best Adam Sandler Movies

10 Best Adam Sandler Movies (Must See!)

Adam Sandler and Netflix just upped the ante of their relationship, with the actor recently promising to work with the company on four more films in addition to the four he was previously contracted for. It highlights an interesting question about Sandler’s career, a question that has been persistently circulating for the better part of two decades: are his best films behind him, or still yet to come?

On the one hand, it’s hard to ask much more of an guy who is not just a household name, not just a prolific actor whose movies have grossed $2.5 billion, but also an award-winning comedian, beloved voice-over actor, producer, and Emmy-nominated writer. On the other hand, there is a strong feeling among critics that Sandler is an entertainer whose true abilities have gone largely untapped, that he possesses a certain artistry in his comedy that has been underused, and to some degree, underappreciated.

Some people argue that it’s because Sandler himself is too lazy to get involved with good films and filmmakers, preferring instead to stick with the mass-appeal slapstick comedies he is most known for. But just because his movies aren’t exactly art house material, does that mean they aren’t good? After all, there’s something to be said for the power to entertain millions of viewers and gross billions of dollars of profit. And at the end of the day, who gets to decide what “good” is anyway?

While critics pan his work and casting directors scan the horizon for younger, edgier actors to fill comic roles, devoted members of Sandler’s huge fan base aren’t arguing over which films of his are “good,” they’re arguing over which are best. With that in mind, here’s a look at the Sandman’s ten best movies so far:

10The Waterboy

Sandler starred in two movies released in 1998 that grossed over $120 million worldwide. The Waterboy, directed (and starred in) by Frank Coraci was one, and the other was The Wedding Singer. Bobby Boucher, Sandler’s character in The Waterboy, is a 31-year-old, socially awkward, emotionally challenged mama’s boy whose sole ambition is to be a good waterboy for the college football program that employs him (in quite a few ways, the character is a throwback to various Saturday Night Live skits that Sandler played in). When that team fires him, Boucher takes his “watering” skills to a different team, this one a hapless loser of 40 consecutive games. But can the right waterboy turn it all around?

The Waterboy received mostly mixed reviews, and quite a few that were just plain bad. It was called “an insult to its genre,” “boring,” “forgettable,” and “mildly amusing,” among other things, and Sandler was nominated for a Golden Raspberry Award for Worst Actor for his role in the movie. A writer for the Washington Post called Sandler’s character a “cretinous, grating loser”. Yet somehow The Waterboy hung on at the box office to gross just short of $186 million on a $20 million budget. Not only was it clearly a giant commercial success, but it also remains one of the most popular and quoted movies in which the actor has starred.

9Billy Madison


Before Billy Madison, Sandler also played in five other films, including 1989’s Going Overboard, which some deride as one of the worst films of all time (and they may have a point). Nonetheless, most people consider Billy Madison, directed by Tamara Davis and released in 1995, to be the real beginning of Sandler’s film career. In it, he plays an unmotivated heir to a Fortune 500 company whose stake in the business is contingent on his returning to public school and completing grades 1-12 in just two weeks. Of course, along the way he falls for one of the school’s teachers and must figure out how to win her love in addition to securing his diploma.

If the plot sounds a little goofball, it’s because it totally is. And it’s likely that no one ever guessed just how many more goofy movies like Billy Madison that Adam Sandler would go on to make, nor how unbelievably rich and famous they would make him. At the time (and for the most part, still) critics did worse than demolish Billy Madison – they basically ignored it. That didn’t stop it from becoming the epitome of a cult classic, and to this day, it’s nearly impossible to find a movie that represents a bigger disconnect between the opinions of fans and professional movie critics. If you like anything else Sandler has been in, but you haven’t seen Billy Madison, it’s worth watching simply for its historical significance. Like, t-t-t-today, Junior!

8The Longest Yard


The Longest Yard was originally a 1974 film starring Burt Reynolds. The 2005 movie by the same name also starred Burt Reynolds, but this time with Adam Sandler playing the lead role. Without giving too much away, it’s about a disgraced ex-NFL quarterback who is serving a prison stint, and is forced to draft a football squad to play against the prison guards. Sports comedies are relatively few in number, and they don’t get much better than this one, which really brings the action, thanks to a cast that includes a number of professional athletes (Terry Crews, Kevin Nash, Steve Austin, Bill Goldberg, Bill Romanowski, Bob Sapp, and more).

The Longest Yard is a comedy, sure, but it’s also a classic underdog tale, with some arrogant prison staff members, Captain Knauer and the warden, Hazen (played by William Fichtner and James Cromwell), that are all too easy to hate. The Waterboy might be the movie that comes to mind when someone puts “Adam Sandler” and “football” together in a sentence, but The Longest Yard is really the better movie – funnier, more believable, and easier to root for. To boot, no other remake of a comedy has fared so well at the box office in the modern era. Critics panned the film (although prominent reviewer Roger Ebert actually gave it a thumbs up), but it still made over $100 million worldwide, proving once again that what Sandler lacked in critical appeal, he made up for with commercial success.

7Big Daddy

After starring in two films the year before that grossed over a combined $240 million, Adam Sandler had a lot to live up to in 1999’s Big Daddy. The actor (and the movie) came through, ending up with another grand total of over $120 million at the box office, which would be the highest total for any movie featuring Sandler until Click came out seven years later. Yet again, a film starring Sandler highlighted the subjective nature of cinema, as Big Daddy took home both the People’s Choice Award for Favorite Comedy Motion Picture, and the Golden Raspberry Award for Sandler as Worst Actor (his first of three). It also got five other Golden Raspberry nominations, including Worst Picture, Worst Director, and Worst Screenplay.

Some men become fathers because they envision children inheriting their business. Some men do it because they want to keep playing with kids’ toys without being made fun of. In Big Daddy, Adam Sandler’s character, Sonny Koufax, becomes a foster father because he’s too lazy to get out of it, and also to win back his ex-girlfriend (who dumped him because he was lazy). Fathering doesn’t mesh so well with laziness, but Sonny makes it work by employing a unique parenting style. So unique that his “son’s” teacher becomes concerned, reports him, and the boy is taken away. Only by now, Sonny has started to learn about all the good points of being a dad, so it’s up to him to get his son back by proving to the system that he can handle the job.

6Anger Management

Almost all of us hate being told how we feel, especially when we already know how we feel. Being forced to take anger management counseling, then, isn’t exactly at the top of anyone’s list. On the other hand, it’s likely that more of us could use therapy than we’re ready to admit, and that’s what makes Adam Sandler’s 2003 comedy Anger Management so relatable. His character, a jilted and underappreciated businessman named Dave, certainly has more than his fare share of repressed emotions, and who better to unravel them than the guy who set him off in the first place!

Jack Nicholson does a great turn as Buddy, Dave’s court-appointed therapist, and Luis Guzman, Woody Harrelson, and John Turturro all contribute to a classically comedic cast. On one hand, Sandler’s recognizable shtick is a big part of Anger Management, and it’s not the only time (far from it, in fact) that we’ve seen him play a character with emotional problems. On the other hand, the film is really built on the dynamic that exists between Sandler and Nicholson, which injects some freshness into what otherwise might be a string of overly repetitive roles from Sandler.

Mixed reviews notwithstanding, Anger Management held its own at the box office, and is still one of Sandler’s better reviewed outings, and the movie also spawned a 2012 television series by the same name, this time featuring Charlie Sheen.

5Reign Over Me

Believe it or not, Adam Sandler is in some movies that aren’t outright comedies. Sure, Reign Over Me has its humorous moments, and there is no escaping the fact that Sandler is unfailingly cast as a fundamentally awkward character, but the subject matter of this film is a far cry from the ludicrous plotlines that audiences were used to seeing him fumble through. In 2006’s Reign Over Me, Sandler is still awkward and fumbling, but this time it’s more or less believable, as he acts out the life of Charlie Fineman, a husband and father who lost his family in the tragedy of 9/11.

This movie isn’t the first time that Sandler played a more “serious” character, and he arguably pulled it off even better in a movie that will be featured a little farther down this list. For him, though, those roles are few and far between, making them all the more poignant as indicators of the real talent and range that he possesses as an actor. Not everyone was happy with Reign Over Me, despite memorable turns by both Sandler and supporting actor Don Cheadle, and it certainly wasn’t the money-maker that his previous outing, The Longest Yard, had been the year before. Still, the film is difficult to dislike, and ranks among the most critically praised of all Sandler’s work. Going into Reign Over Me expecting a comedy would be a mistake, but so would not going into it at all.

4Happy Gilmore

When David Dugan directed Happy Gilmore, he probably had no idea that he would go on to direct seven more films starring Adam Sandler during the next two decades. In fact, his relationship with Sandler is arguably what Dugan is most known for among film buffs, and it may be that 1996’s sports comedy Happy Gilmore is still his best work. Critics basically destroyed the film, which earned Sandler his very first Golden Raspberry nomination for Worst Actor (he didn’t win, but would go on to be nominated nine more times and win three times).

Negative reviews are just words, though, and they did nothing to stop Happy Gilmore from grossing well over $25 million worldwide, or from becoming a cult favorite among Sandler’s fan base. In particular, audiences are unlikely to ever forget the famous fight scene in which Sandler’s character, an ex-hockey player turned unlikely pro golfer, dukes it out with none other than Bob Barker during a celebrity golfing match. So spectacular was the brawl that it earned an MTV movie award for Best Fight, and also raised ratings for Barker’s show The Price is Right.

Notably, Happy’s unique golf swing has gone on to become a cultural icon of its own, what with amateur golfers frequently emulating it, and even some professional golfers using it as a training device. Is it a good swing? Well, that’s debatable, but at least we can say it’s not nearly as good as the movie.

3Funny People

Director Judd Apatow is well known for his comedies, which include Knocked Up and The 40 Year Old Virgin. Despite those movies being commercially successful while Funny People was a box office bomb, many people still consider the latter to be his greatest work. The same goes for Sandler’s performance in the film, which ought to make sense by now, given the seemingly inverse correlation between critical reception and overall popularity of his work. Once again departing from his traditional slapstick fare in this 2009 film about a comedian who has terminal cancer, Sandler plays a more true-to-life role. It’s still funny, but it’s also serious. And sometimes, seriously funny.

There’s a little bit of irony going on in Funny People, with Sandler portraying George Simmons, an aging comedian whose films are poorly received and considered by many to be low-brow works of art. But, as in Reign Over Me (and some of Sandler’s other films, as well) the undertone of sadness is what gives the film so much life. Sandler and his character, George, are similar in that both are talented individuals whose work doesn’t always do justice to their abilities. A stellar cast that included Seth Rogen, Leslie Mann, Eric Bana, Jason Schwartzman, Jonah Hill, and Aziz Ansari made Funny People actually funny, and Apatow did a good job reigning in all that talent. Despite a few glaringly negative criticisms, the film was well-received, and for a change, gives the audience an Adam Sandler they can honestly and easily empathize with.

2Punch-Drunk Love

Pretty much all of the movies that feature Sandler in a semi-serious role are on this list, and it’s not without a good reason – that’s when he’s almost undeniably at his best, with a script, character, and director that work together to bring out his real talent. Punch-Drunk Love, released in 2002 and featuring writer/director Paul Thomas Anderson, is by far the most critically praised of Sandler’s films, even earning the actor a Golden Globe nomination for Best Actor and a much-deserved win for Best Actor at the Gijon International Film Festival. It also netted Anderson the award for Best Director at Cannes Film Festival, and a Palm d’Or nomination for the film itself.

Maybe the best thing about Punch-Drunk Love is that it doesn’t try to be anything it’s not. It’s nothing like Sandler’s more common outings as a purveyor of cheesy jokes, but it’s not a full-fledged drama, either. It lands somewhere squarely within “dramedy” territory, with Sandler displaying both his awkward, artisan humor, and a surprising dark side that lends to the films compelling intrigue. Of course, as is par for the course with Sandler’s films, what Punch-Drunk Love had in critical appeal, it lacked in widespread popularity, and it came up just shy of recouping its $25 million budget. The trend is so pervasive that one could almost judge the best Adam Sandler movies just by ranking them according to how little they made. That would throw off this list a bit, but hey, whatever. Speaking of which, the top spot simply must go to:

1The Wedding Singer

Despite all this talk about Adam Sandler’s capability of taking on characters who have true depth, the bottom line is that he is, first and foremost, an expert at eliciting laughs. The height of Sandler’s film career, then, must be those moments when he is true to that calling above all else. Of course, it doesn’t hurt anything if depth of character is still present, but the truth is that we watch Sandler’s movies to be amused, and that’s why his artier fare has never pulled its weight at the box office. What did pull its weight was 1998’s The Wedding Singer, in which Sandler plays a 1980s wedding performer who falls in love with a waitress, played by Drew Barrymore. The plot develops out of the fact that the singer and the waitress are already engaged, but to other people. Hilarity ensues as they figure out their future one wrong turn at a time.

Along with Sandler’s other 1998 hit, The Waterboy, The Wedding Singer was directed by Frank Coraci, and is widely considered among the best works of both men. Drew Barrymore was ingenious as well, and her and Sandler’s chemistry was profound enough that they teamed up again six years later in another romantic comedy, 50 First Dates. The Wedding Singer is unique among Sandler’s movies in that it did fantastic at the box office and still managed to score points with critics. To this day, it’s debatable whether Sandler has ever appeared in a movie that is in such equal parts funny and light, yet compelling and relatable.

In Conclusion

Naming ten great Adam Sandler movies really isn’t very difficult – but naming the ten best? That’s a real challenge. Narrowing it down meant leaving off movies like Click, another Frank Coraci-directed fantasy/comedy in which Sandler plays a character with the ability to remote control his life, and Spanglish, another respectable “dramedy” that shows off Sandler’s acting range. Of course, that’s not to mention other hits, like Don’t Mess With the Zohan, Grown Ups, and I Now Pronounce You Chuck and Larry. Even his Count Dracula voice-over in the Hotel Transylvania franchise can serve as another great example of his work.

When Punch-Drunk Love came out, famed film reviewer Roger Ebert gave it three and a half stars out of four, his highest rating of any Adam Sandler movie, and doubted in his review if Sandler could “go on making those moronic comedies forever.” Well, the jury is still out on that one, and if his recent movies with Netflix (The Ridiculous 6, The Do-Over) serve as any indication, more “moronic comedies” is probably what we can expect from Sandler’s future. But hey, aren’t moronic comedies exactly what we’ve loved from him all along?


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