Adam Sandler has built an entertainment empire over the past three decades. The former Saturday Night Live cast member has either starred in or produced dozens of memorable films in that time. Not to mention, his Happy Madison Productions has given regular film roles to many of Sandler’s pals as well, such as Kevin James, David Spade, Rob Schneider, Chris Rock, and others. Sandler’s deal with Netflix has also been a lucrative venture, where the majority of his most recent films have appeared. Such a lengthy deal with Netflix would have never happened if it weren’t for the huge success of so many of his other movies beforehand. Love him or hate him, Sandler knows how to bring in a captivated audience time and time again.
While his comedic performances are often panned by critics, Sandler’s dramatic roles are much better received. He’s also had some very successful voice-acting roles in recent years. Fans usually seem to respond positively overall, pretty much no matter what he does. Many of Sandler’s best films are the ones with heart, where his characters can make sacrifices for others. He’s created numerous characters that often border on crazy, entitled, or with something unique about them, whether it’s physically or emotionally. This formula seems to work very well for Sandler, and it’s helped him keep a consistent string of hit movies coming for a long time. This bankable movie status has given him the freedom to have projects written specifically for him. And at the end of the day, Sandler’s one of the best draws in all of Hollywood. As long as he continues to make films, there will likely be a lot of people interested in seeing them.
Updated on September 3rd, 2023, by Rachel Johnson: This article has been updated with additional content to keep the discussion fresh and relevant with even more information and new entries.
14 Mr. Deeds (2002)
Adam Sandler and Winona Ryder shared the screen when they headlined the 2002 comedy Mr. Deeds, a remake of the '30s flick that features the funny man as a kind-hearted pizzeria owner who inherits a family member's billion-dollar fortune.
He soon finds his life completely transformed for the better and for the worse. While by no means a hit with critics, the rags-to-riches film was a success at the box office and once again showcased Sandler's charisma and overwhelming likability as a performer.
13 Spanglish (2004)
Sandler started branching out into more mature roles when he co-starred alongside Téa Leoni and Paz Vega in the romantic dramedy Spanglish, centering on the Clasky family as husband and wife John and Deborah invite a Mexican immigrant to come and stay with them as a housekeeper along with her young daughter, resulting in a culture clash and mounting tensions.
Though it failed to make a splash at the box office, some critics were appreciative of Sandler's efforts to shift from solely a comedic actor to a serious leading man, and the film paved the way for future sophisticated projects.
12 Grown Ups (2010)
While not a critical darling, Grown Ups was a fun family buddy-comedy that made a lot of money. It spawned an even less acclaimed sequel, however, as with many of Adam Sandler’s films, the point is for audiences to have a good time.
As a viewer, the movie makes you feel a bit like you’re included in the fun and part of Adam Sandler’s character’s odd group of life-long friends. The cast includes frequent collaborators like Kevin James, David Spade, Chris Rock, Rob Schneider, and even Salma Hayek.
11 Reign Over Me (2007)
In one of Sandler's most somber and poignant films to date, the usual slapstick performer demonstrated his dramatic range when he appeared alongside Don Cheadle in Reign Over Me. He portrayed a grief-stricken man who tragically lost his family in the September 11 attacks and has become the shell of his former self.
He finds new meaning in life after reconnecting with his old college roommate. Sandler earned rave reviews for his compelling performance, with the New York Daily News writing, "Cheadle is good, as always, but Sandler's portrayal of a guy on the perennial brink of a psychotic breakdown is amazing."
10 Funny People (2009)
Adam Sandler, Seth Rogen, and Leslie Mann were fantastic when they starred in the black dramedy Funny People, which tells the story of a popular but depressed comedian whose life is turned upside down after he is diagnosed with a terminal illness.
He sets out to make a difference by taking an aspiring comedian under his wing to mentor him on the ins and outs of the stand-up world. Director Judd Apatow ended up casting his former roommate Sandler after seeing his impressive performance in Reign Over Me, and while it wasn't a commercial hit Funny People further showed that Sandler could do more than just low-brow comedies.
9 Hotel Transylvania (2012)
Sandler lent his distinct voice to the animated flick Hotel Transylvania, appearing as legendary vampire Count Dracula, who has built a massive and grand resort where he can safely raise his daughter Mavis (Selena Gomez) and where monsters can go to escape the suspicious eye of humanity.
When a human (Andy Samberg) sneaks into the hotel and falls in love with Mavis, Drac must try to keep the security breach under wraps before his fellow monsters find out. Hotel Transylvania was both a critical and commercial success and went on to launch a lucrative franchise that led to three sequels.
8 50 First Dates (2004)
Adam Sandler and Drew Barrymore decided to work together again about a decade after their first film together, which kicked off an ongoing collaboration between them. The results are still solid, and 50 First Dates tells an interesting love story about a girl with brain damage who forgets who she is every day.
That means she also forgets the man she’s in a relationship with, which makes things difficult for Adam Sandler when he falls in love with her. Sandler and Barrymore show they still have chemistry together, even many years after The Wedding Singer.
7 Just Go With It (2011)
Adam Sandler is also known for on-screen chemistry with Jennifer Aniston, who in Just Go With It pretends she’s his soon-to-be ex-wife to help him secure a relationship with the girl of his dreams, played by Brooklyn Decker.
The plot is predictable, and the premise is a little ridiculous. However, it’s enjoyable to see if Sandler and Aniston will be able to keep the charade going or not while simultaneously falling for one another.
6 Anger Management (2003)
Adam Sandler stars alongside screen legend Jack Nicholson in a film about, you guessed it, anger management. Sandler is sentenced to taking anger management classes after an incident on an airplane that leads to his doctor moving in with him to help him get better.
As you can probably imagine, the comedic conflict between the two only grows from there. Anger Management also stars Marisa Tomei, Luiz Guzman, and Woody Harrelson. A television show was later made with actor Charlie Sheen in the starring role that was based on this movie.
5 The Waterboy (1998)
One of Adam Sandler’s most memorable roles came in The Waterboy as Bobby Boucher Jr., a stuttering mentally challenged man who is the water boy for the University of Louisiana football team. Despite being part of the team for 18 years, Bobby is constantly mocked until he’s eventually fired. He soon joins the down-and-out South Central Louisiana State University Mud Dogs to be their water boy but is eventually convinced to play for the team.
Bucher’s surprising skills on the field led the Mud Dogs to great success. Of course, in the big game, Bobby must play against and beat his old team, the University of Louisiana, to earn their respect and perhaps get a little revenge.
4 Click (2006)
In Click, Adam Sandler plays a character who’s always working and never has enough time to spend with his family. He eventually meets an inventor (played by Christopher Walken) who gives him a special remote control that controls time.
Sandler speeds through what he feels are the boring, day-to-day moments of his life to skip to the best parts. However, he quickly realizes this is a mistake as he then has no recollection of special moments he shared with his wife and kids over the years he skipped through. Only at this point does he realize what he truly has and fights to get back the time he lost.
3 The Wedding Singer (1998)
Set in the 1980s, Sandler plays a man whose girlfriend cheats on him in The Wedding Singer. If that wasn’t bad enough, he’s also a wedding singer who must constantly play for loving couples to make a living.
He eventually meets Drew Barrymore’s character, who is about to marry an evil man who does not love her. Sandler and Barrymore start to fall for one another and Sandler concocts a scheme to expose Barrymore’s fiancé for whom he truly is and wins her love at the same time.
2 Billy Madison (1995)
In Billy Madison, one of Sandler’s earliest starring roles, he plays a rich and spoiled character named Billy Madison, whose Father is tired of his partying ways. The elder Madison is ready to hand over the family business to his son but realizes he may not be capable of handling the responsibility.
It’s also revealed that Billy Madison’s Father bribed his son’s teachers to pass him in school during his entire academic life and therefore never graduated on his merit. This prompts a bet where Billy (Sandler) must re-take every school grade in two-week increments and pass completely on his own to gain control of the family company, keeping it from being turned over to Madison’s conniving associate instead.
1 Happy Gilmore (1996)
For those who’ve followed Sandler’s career, there is no movie funnier in his entire filmography than Happy Gilmore. Sandler plays a down-on-his-luck hockey player who discovers he can hit a golf ball at a pro distance. Around this same time, Gilmore’s grandmother is stuck in a nursing facility and is about to lose her home. Happy Gilmore realizes that playing golf may give him the money he needs to save her home for her, so he reluctantly agrees to give it a try. With some help from Chubbs (played by Carl Weathers), Gilmore proves capable of playing on the professional golf circuit. Gilmore’s hockey-like antics on the fairway do not go over well with golf purists, however, but win him many casual fans in the process.
One of the highlights of the film is Sandler’s fight with The Price is Right game-show legend Bob Barker during a celebrity golf tournament. The finale of the film leads up to a showdown between Happy Gilmore and golfing rival Shooter McGavin, who’s threatened to buy Gilmore’s grandmother’s home from out under him. This movie built on the momentum of Billy Madison. However, this time Sandler plays a more likable character and has a more rounded storyline “bad guy” to compete against. Happy Gilmore also solidified Sandler’s place alongside other comedy heavyweights of the time, such as Jim Carrey, Ben Stiller, and Mike Myers.