bilbo/MovieStillsDBAdam Sandler has certainly carved himself a unique space in Hollywood, becoming synonymous with a brand of comedy that marries slapstick humor, heartfelt moments, and unforgettable characters. From the uproarious laughter elicited by Happy Gilmore to the poignant and dramatic turns in Uncut Gems, Sandler’s range as an actor and filmmaker is impressive. In this list, we honor these films by ranking the 20 greatest Adam Sandler films of all time.
20. Benchwarmers
Zayne/MovieStillsDBBenchwarmers was never exactly a comedy film known for its rave critic reviews. Still, we think it’s one of the most memorable. A millionaire who loves baseball bankrolls his dorky son’s little league team in an effort to stick it to the bullies — until it’s discovered that one of the nerds was actually a bully themselves. The Adam Sandler-produced film starring Rob Schneider and David Spade was good for some cheap laughs and a few memorable lines, but nothing groundbreaking.
19. That’s My Boy
RobertMcClaine/MovieStillsDBA film that can perhaps be labeled in the category of “so bad, that it’s good”. That’s My Boy certainly pushes the envelope with its humor, attempting to navigate complex topics with a light-hearted Adam Sandler touch that might not hit the mark for everyone. While it strives to be an absurd comedy, akin to shows like It’s Always Sunny in Philadelphia, its execution feels off-kilter, portraying sensitive subjects in a surprisingly casual manner. The film also draws criticism for its harsh treatment of Andy Samberg’s character, painting him in an unflattering light compared to Sandler’s more beloved, flawed protagonist. Despite this, the movie has some great lines and moments — a true “no-brain” comedy that one can put on and (probably) get enjoyment.
18. Little Nicky
cemeteryschild/MovieStillsDBLittle Nicky was quirky, off the wall, and not something you’d expect from his typical works. Sandler plays the role of a good-natured devil who is sent to hell to save the world from more devious characters. Alongside a talking bulldog and other companions, we watch his chaotic journey filled with laughs and entertaining battles. In his film catalog, it was always considered to be a good film — yet not quite his most memorable.
17. Blended
suryaaab/MovieStillsDBOne thing you may notice about Adam Sandler films is that he likes to stick with actors he has a history working with. Drew Barrymore is no exception, and they are reunited once again in Blended. Playing the roles of single parents, they end up sharing a suite on a luxurious African safari vacation with their children. Despite their initial misgivings, the trip brings them closer, leading to unexpected family bonding and laughter. Released in 2014, the film faced critique for its predictable storyline and some lowbrow jokes but was appreciated for Sandler and Barrymore’s compelling dynamic.
16. Hotel Transylvania
Zayne/MovieStillsDBAdam Sandler tried his hand as a voiceover in an animation film with Hotel Transylvania. This film was fun. It was a new take on the stories of classic monsters with its setting in a fancy hotel designed as a getaway for monsters from the human world. Adam Sandler brings Dracula to life, playing the hotel’s owner and a dad who just wants to throw the perfect birthday bash for his daughter Mavis, voiced by Selena Gomez. Things get complicated when a human, Jonathan (Andy Samberg), accidentally finds his way to the hotel, causing Dracula to panic. The movie, which hit theaters in 2012, won over many with its creative animation, comedic moments, and touching story about a father and his daughter.
15. I Now Pronounce You Chuck And Larry
Zayne/MovieStillsDBWould this film be made today? Signs point to no. Still entertaining? Absolutely. This film stars Sandler alongside Kevin James — who plays the role of two straight men who pretend to be gay in order to exploit legal loopholes with their marriage. While the film claims to eliminate stereotypes, it still received criticism for reinforcing them at the same time. Regardless, Sandler and James had great chemistry as a comedic duo, and it received good critical reception. It was a unique twist for Sandler, as it was a film that tried to blend social commentary with low-brow comedy.
14. Anger Management
Zayne/MovieStillsDBAnger Management sees Sandler star alongside Jack Nicholson, one of the biggest costars of his comedic film career. Sandler plays a quiet businessman who ends up in an anger management class because of a misunderstanding. There, he meets the quirky therapist Dr. Buddy Rydell, played by an energetic Jack Nicholson. The movie did well financially, and Anger Management proved that Sandler could pull in big names for his comedies and remain a strong force at the box office.
13. Grown Ups
Zanye/MovieStillsDBA comedic romp that features the four most memorable Sandler cast members: Kevin James, Chris Rock, David Spade, and Rob Schneider. The group of old friends reunites with their families over a Fourth of July weekend, facing the challenges of being adults while still keeping their youthful spirit alive. Despite being released in 2010 to critical reviews that were mixed, the movie resonated with viewers for its sense of nostalgia and the strong bond between the main characters. The film found success at the box office, showing that there’s a significant audience for stories about friends navigating life’s ups and downs with humor.
12. Just Go With It
bilbo/MovieStillsDBA near-perfect exemplification of an Adam Sandler film. It’s a light, stupid, funny film that mixes stories of personal growth. Sandler’s character, a plastic surgeon named Danny Maccabee, ropes in his assistant, Katherine (played by Jennifer Aniston), to act as his soon-to-be ex-wife to maintain a lie he told his younger girlfriend. Honorable mention to the surprisingly funny Dave Matthews.
11. Hustle
yassi/MovieStillsDBProduced by Adam Sandler alongside other big names you may have heard of such as LeBron James, Hustle is a more modern Sandler film in that it tackles a more serious tone. In the cutthroat arena of professional sports, Sandler plays a basketball scout who spots who he believes to be a generational talent out of Spain. In an effort to revive both of their careers, their stories intertwine into what turns out to be an engaging overall film. It was a new direction for Sandler to take, and we think he hit it well. Shout out to the acting skills of Anthony Edwards.
10. Click
raven76/MovieStillsDBThere’s a high likelihood you will shed at least one tear by the end of this film. Surprisingly poignant, it explores the consequences of a life lived on autopilot. Michael (Sandler) discovers a magical remote that allows him to fast-forward through undesirable moments in his life, only to realize the value of the very moments he’s skipping. As the film progresses, it takes a surprising turn, delving into themes of family, time, and missed opportunities. While it didn’t receive the best critical reviews, it is considered by many fans to be one of his better works.
9. The Longest Yard
Zayne/MovieStillsDBThis film perfectly balanced heart with humor. Released in 2005, this remake of the 1974 classic brought together a diverse cast, including Burt Reynolds, who starred in the original film. What sets The Longest Yard apart is its story of underdog triumph, teamwork, and redemption, elevating it past just a comedy. Critics had mixed feelings, but audiences loved the combination of action-packed football scenes and the comedic dynamics among the inmates. An interesting fact about the film is that several professional athletes, including Michael Irvin and Bill Romanowski, played roles, adding authenticity to the game sequences. This unique mix of genuine sports action, comedy, and a story of second chances is what made The Longest Yard so enjoyable for many viewers.
8. Mr. Deeds
pmv76/MovieStillsDBA movie tale as old as time: a small-town guy inherits a massive fortune. Longfellow Deeds (Sandler) finds himself navigating the shark-infested waters of big-city corporate greed. Sandler’s character, with his down-to-earth charm and unexpected wealth, encounters a series of comedic situations, all while developing a romantic connection with a reporter played by Winona Ryder — who initially deceives him for a story. This film was undoubtedly one of his best and was widely praised for its blend of humor, romance, and moments of genuine sincerity.
7. The Wedding Singer
richard3rd/MovieStillsDBOne of the most beloved rom-coms in history. It hits that sweet spot of humor, heart, and 80s nostalgia that resonated with audiences almost perfectly. Sandler and Barrymore’s on-screen chemistry exemplified this by offering a sweet, engaging narrative that explores themes of love and disappointment. Critics and audiences alike praised the film for its charming story, comedic moments, and the leads’ performances, making it one of Sandler’s most revered movies.
6. 50 First Dates
L. Cohen/WireImage/Getty ImagesThe third (and best) Barrymore/Sandler duo film. 50 First Dates tells the heartwarming tale of Henry (Sandler), a veterinarian, who falls for Lucy (Barrymore), a woman with short-term memory loss who relives the same day over and over. Set in picturesque Hawaii, the film combines comedy with touching moments of romance, as Henry devises creative ways to win Lucy’s heart every single day. Audiences were particularly moved by the film’s exploration of unconditional love and the lengths one will go to keep a connection alive, with the ending scene often cited as especially touching.
5. Big Daddy
aprobgrovy/MovieStillsDBPerhaps one of the funniest films in the entire Sandler collection. In this film, he plays a lazy law school graduate who unexpectedly adopts a child (Cole Sprouse) in a bid to impress his girlfriend. Along the way, the father and son duo get up to hijinks, pranks, and genuine bonding moments. In addition to Click, it was one of Sandler’s most heartwrenching films, which will also likely leave you in tears — both out of sadness and laughter.
4. Waterboy
Zayne/MovieStillsDBUndoubtedly, The Waterboy was one of Sandler’s most beloved films. He plays the role of Bobby Boucher, a timid waterboy with a hidden talent for football, leading to his rise as the star player of his college team. Released in 1998, the film combines Sandler’s comedic ability with an uplifting tale of an underdog, making it a hit with audiences. Kathy Bates delivers a memorable performance as Bobby’s protective mother, and Henry Winkler shines as the encouraging Coach Klein. The film also features numerous cameos from real-life sports figures, including Lawrence Taylor, Bill Cowher, and Chris Fowler.
3. Uncut Gems
warnerchild/MovieStillsDBPerhaps the most unique Sandler movie to date. It’s a movie with a plot that may seem more serious and dark but ends up being quite humorous at the same time. He plays a New York City jeweler with a penchant for high-stakes gambles and is addicted to finding the next big score. His life quickly spirals into chaos as he tries to sell a rare Ethiopian gemstone to clear his debts, all while juggling threats from collectors and personal turmoil. Directed by the Safdie Brothers, Uncut Gems was a hit for both critics and viewers. This is a direction we wouldn’t mind seeing Sandler take more of.
2. Billy Madison
Zayne/MovieStillsDBOne of the most essential comedies of the ’90s — it was one of his first (and most successful) hits to date. Audiences immediately loved the absurd story and comedy, combined with endless quotable moments and stories of personal growth. Not to mention that even today, the humor and jokes still hold up incredibly well — something that is increasingly rare, especially for a 90s comedy. This film more or less solidified Adam Sandler as a Hollywood comedy mainstay.
1. Happy Gilmore
aprobgrovy/MovieStillsDBOne of the greatest films ever. It’s the perfect Adam Sandler film: a blend of sports, comedy, and stories of personal growth, all with a touch of the heart in a way that only Sandler can. In a bid to save his grandmother’s house from foreclosure, he turns to professional golf tournaments to raise funds. It features some of the most quotable moments ever in a film, and even to this day, people will reference them happily — ensuring endless entertainment even way after its release.
