Adam Sandler is a name synonymous with comedy, and few other comedians have led a career quite like his. That paired with the acclaim of his work taking somewhat of a dive in recent years may cause some to take for granted just how many great things he's been in over the years. This list chronicles the best of the best when it comes to Sandler, and should serve as a reminder as to why he's still so popular today. We're dividing these movies up into categories that best represent what Sandler has delivered to audiences over his long career: the '90s, the 2000s, his more dramatic movies, his animated work, his Netflix offerings and a few of his underrated projects.
The '90s
We begin with what many would consider Adam Sandler's peak era, the '90s. When people say they love Sandler, these are the movies that are often referenced, and rightly so because they remain some of the best he's performed in during his career.
Billy Madison
The premise of an adult man repeating kindergarten through 12th grade in order to gain control of his father's business is an admittedly ridiculous premise, but Sandler just makes it so fun the whole way through. The one-liners that can be quoted throughout this movie are endless, and will still get laughs even after multiple re-watches. Much like the O'Doyle family, this film rules.
Happy Gilmore fundamentally changed the game of golf, even if it wasn't for the best. This movie is the reason driving ranges ask that golfers not take a "running start" on golf drives and possibly why some younger kids become interested in golfing to begin with. Let's also not forget the iconic "Endless Love" scene that balances romance and comedy in a way Sandler's films have mastered.
The Wedding Singer
A lot of Adam Sandler's iconic films of the '90s had a tinge of romance, but The Wedding Singer is definitely one of the few of this era where romance came before the comedy. While Sandler's performance as Robbie Hart was great, apparently audiences really responded to the dynamic Sandler shared with Drew Barrymore. At least, that's what we're assuming seeing as they were in another romantic comedy together years later.
The Waterboy
One of the best things about Adam Sandler movies is there are some ideas that wouldn't work for anyone else but him. You don't believe me? Try to imagine anyone else playing the role of Bobby Boucher, the all-star college football athlete primarily driven by his rage. This one has plenty of belly laughs, a great performance by Henry Winkler and a notable message that mama doesn't always know what's best.
Big Daddy
Adam Sandler plays an adult man child who essentially adopts a child to win a woman back. Of course, it becomes more than that as the story progresses, and soon his character Sandy has trouble imagining his life without the boy. For older Sandler fans trying to get their teens to get into Sandler's older films, just casually bring up that Cole Sprouse (from Riverdale) tag teams the role of Julian with his twin brother Dylan.
The 2000s
We're now at the 2000s, which was still a good time to be Adam Sandler. This era started off with more of the same comedy projects audiences expected from the actor, but slowly evolved throughout the decade into something entirely different. Enough with the cryptic sentences, let's get back into things.
Mr. Deeds
A good guy gets a lot of money and uses it to improve the lives of others; what's not to love? Mr. Deeds is the perfect combination of feel good and funny, and features great supporting performances from Winona Ryder and John Turturro. Also, it put the dream of putting Hawaiian Punch in water fountains out into the universe, which means there's a chance we too can one day experience that luxury.
50 First Dates
Drew Barrymore and Adam Sandler get back together again for a film that, while increasingly improbable the longer one things about it, is still pretty great. Kick back, relax and only wonder how long that tape Lucy watches is after the credits roll!
Click
Click was one of those surprise films, mostly because it starts off as the typical Adam Sandler romp and then gets dark real quick. It's a real bummer for anyone looking for the standard comedy, but really great for those looking to be surprised by what becomes a film surprisingly deeper than it initially seems.
The More Dramatic Movies
Comedy is Adam Sandler's main strength, but as many of his fans know, he has a more serious side. While his serious endeavors aren't as celebrated as his typical romps, there are certainly a few gems that fans of the actor should check out. After all, some of these have double-to-triple the critical acclaim of some of his comedies.
Punch-Drunk Love
As stated before, Adam Sandler is good at the whole being funny, but romantic thing. It's worked for him in several films before, and it really peaked in Punch-Drunk Love. It's one of the darker films Sandler's done, and a form of comedy that explores the grim reality of battling loneliness in adulthood. It's a little heavy, but a great ride from start to finish.
Reign Over Me
Reign Over Me may not be the highest rated of the "serious Sandler" genre, but damn if it isn't one of the saddest. Don Cheadle and Adam Sandler do a fantastic job of telling the story of two friends who find themselves in need of each other for totally different reasons. It'll make you cry, even if the plot is a bit uneven throughout.
The Animated Work
Live-action is just one of the places Adam Sandler's taken his comedy, of course, as he's also done a handful of projects in the world of animation. Granted, he's done far less than some other actors and actresses, but there's a couple projects in his animated filmography certainly worth checking out.
Eight Crazy Nights
There aren't a ton of Hannukah movies in general, let alone ones that have a mainstream appeal. Eight Crazy Nights broke that mold, and while it isn't as iconic as some other films, it's certainly worth watching again and again. If 6th grade me was a part of The Academy back when this movie came out, "Bum Biddy" would've at least gotten a nod for Best Original Song.
Who would've thought a franchise about a Dracula and his daughter running a hotel would be so successful? Seriously, it would be surprising to learn even the most optimistic producer of these movies could've guessed we'd be talking about a fourth movie happening, at least in theaters. Adam Sandler's Dracula may not be the only factor in what makes these films special, but he certainly helps.
Netflix Movies
We're now at a modern era of Adam Sandler, which we like to dub as the Netflix Sandler. Adam Sandler's deal with Netflix has spawned quite a few films, and while most of them haven't been viewed in a positive light, the era is not without its merits. In all fairness, there is less to appreciate, but there are two in particular that shouldn't be missed.
The Meyerowitz Stories
For whatever reason, critics tend to love Adam Sandler the more sad the movie he's in is. The Meyerowitz Stories may have gotten Netflix booted from Cannes but the streaming service can hang its hat on being one of Sandler's most critically acclaimed films of all time and quite possibly the first to get legitimate Oscar buzz. Honestly, that's arguably worth more in bragging rights.
The Do-Over
David Spade and Adam Sandler have worked a lot with each other throughout their careers, but none of it tops their work together in The Do-Over. The chemistry these two have really makes one wonder why the '90s weren't full of these guys co-starring in lots of different movies. Those with a subscription should do themselves a favor, and watch this one immediately.
The Underrated Projects
We're close to the end, which means it's a perfect time to hit the Adam Sandler films that are still great, but have faded in popularity in the years since they hit theaters. Each of these were great at the time, and perhaps may be yet again if the world chooses to embrace them en masse once more.
Bulletproof
Bulletproof essentially solidified in Hollywood's eyes that Adam Sandler has no place in action films, even if it is a comedy. It's a real shame because the film is not nearly as bad as some say, and a rare collaboration between the actor and Damon Wayans. Provided one has low expectations going in, this is a great film from start to finish.
Little Nicky
Hot take, Popeye's Louisiana Kitchen has never had better advertising ever. Adam Sandler's odd tale about a son of the devil trying to take over the family business. The film bombed and was viewed as a commercial failure, but it's well worth the price of admission if found on a streaming service or in a bargain bin.
Anger Management
Adam Sandler has had many iconic acting team ups over the course of his career, with some actors and actresses appearing in his films again and again. Jack Nicholson was not one of them, but it really should've happened again after Anger Management. The way these two go at each other throughout the movie is hilarious, and there are so many quotable lines from this one that make it so easy to watch again and again.
Those who think their favorite Adam Sandler movie was unfairly left off the list can state their case in the comments below. For more on Sandler and his fans, read up on the dude who managed to watch one of the actor's films every day for a year straight.
