Like it or not, Adam Sandler is among the most successful movie stars of the last three decades and has remarkably been able to make films that have resonated with multiple generations of comedy fans. While many former alumni of “Saturday Night Live” struggled to develop film careers, Sandler developed his own brand of ridiculous comedies, which led to the development of Happy Madison Productions. Despite the scathing reviews that many of his films earned from critics during their initial release windows, several have grown cult fandom from those who grew up with them. Sandler was also ahead of the game when it came to the profitability of streaming, as he was among the first Hollywood stars to sign a deal with Netflix.
Sandler has certainly been known to phone it in, as films like “Grown Ups,” “Little Nicky,” “Blended,” and “Jack and Jill” rank among the worst comedies of the 21st century. That being said, Sandler is a much better dramatic actor than he is often given credit for; even flawed films like “Funny People,” “Spaceman,” and “Men, Women & Children” gave him the opportunity to show his depths as a performer. 2025 marks a specifically interesting year for Sandler, as it features two of the wildest swings of his career; in addition to starring in the long-anticipated sequel “Happy Madison 2,” Sandler will also be appearing alongside George Clooney in “Jay Kelly,” the latest film from Noah Baumbach. Here are the eight best Adam Sandler movies, ranked.
8. Hustle (2022)
While the majority of the films that Sandler has made during his deal with Netflix have been lowest-common-denominator comedies like “The Week Of” and “The Ridiculous 6,” he also made room within his schedule for “Hustle,” a relatively grounded drama about a down-on-his-luck basketball scout trying to promote a new star player. Even though it didn’t receive a mainstream theatrical release, “Hustle” represents the type of mid-budget star vehicle aimed at an adult audience that Hollywood simply doesn’t make anymore. Unfortunately, it failed to land with as much impact as it likely would have had it earned a theatrical rollout. Sandler received a nomination at the Screen Actors Guild for Best Actor, and could have potentially been in contention for an Academy Award.
Sandler has always been great at playing an underdog, and “Hustle” is a refreshingly mature opportunity for him to play a character who has been denied an opportunity to do what he does best. He is a noted sports fan (as evidenced by the many athletes who make cameos in his comedy films), and his genuine passion for the sport of basketball comes across in “Hustle.” There haven’t been that many genuinely great basketball films since the 1990s classics like “White Men Can’t Jump” and “Blue Chips,” but “Hustle” is a perfectly digestible, highly entertaining look at the competitive world of athlete selection. Even for those who aren’t basketball junkies, it’s an enthralling character drama with one of Sandler’s most reserved performances.
7. 50 First Dates (2004)
“50 First Dates” was released at a curious point in Sandler’s career, as he had begun trekking into family-friendly territory with films like “Click” and “Anger Management,” which felt a bit too saccharine for a comedian who had traditionally been hailed as transgressive. At the same time, Sandler began to feel like he represented the “old guard” of comedy, as directors like David Gordon Green, Adam McKay, and Judd Apatow had been making nastier, meaner comedies that were far more mean-spirited and raunchy. “50 First Dates” could have easily been the nail in the coffin of Sandler’s career, but it surprisingly turned into one of the most charming, sincere projects he’d ever appeared in. Sandler is often only as good as his screen partner, and in Drew Barrymore, he found a co-star whose sensibilities perfectly matched his own.
Sandler may enjoy being the butt of jokes at his own expense, but “50 First Dates” allowed him to play a genuinely sweet, affectionate character whose mistakes are made with the best of intentions. By steering away from cheap jokes at the expense of people who are different, Sandler managed to give an affectionate performance, which allowed the film’s emotional intelligence to distract from some of its narrative coherence. It’s the type of odd role that only Sandler could have pulled off; it’s hard to imagine that contemporaries like Will Ferrell, Seth Rogen, Jason Segel, or Jonah Hill could have pulled off the blend of silliness and sweetness that made “50 First Dates” so special.
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6. Billy Madison (1995)
“Billy Madison” was the first real showcase for Sandler as a leading man, as he had previously only given supporting turns in “Airheads,” “Coneheads,” “Mixed Nuts,” and a few other smaller projects. To capitalize on the types of ridiculous characters that he often played during his run on “Saturday Night Live,” Sandler offered his purest, wackiest performance ever as an overgrown man-child who literally has to go back to school to prove himself. It’s one of the most nonsensical plots of any mainstream studio comedy, and to the credit of “Billy Madison,” the film doesn’t have any pretensions about its importance. While there’s a slight bit of satire about the selfish nature of business wheeling and dealing, “Billy Madison” is mostly an excuse for Sandler to act like a selfish infant and scream absurd phrases.
The brilliance of what Sandler does in “Billy Madison” is that he actually manages to elevate what felt like a one-joke sketch into an engaging narrative. There was a risk that the titular character could grow beyond irritating very quickly, but Sandler was willing to go further and further with each minor set piece, all whilst adding a bit of heart that made the weirdness go down smoother. Like Robin Williams or Bill Murray before him, Sandler excelled at making films for children that were not afraid to get immature. It also initiated his working relationship with many of his recurring co-stars, including Norm MacDonald, Chris Farley, and Steve Buscemi.
5. The Wedding Singer (1998)
Critics had grown wary of Sandler’s man-baby persona by the end of the 1990s, and thus “The Wedding Singer” offered him the first opportunity to prove that he could actually act. While it contains many of the physical shenanigans and goofy one-liners that were present within his earlier work, “The Wedding Singer” is a legitimately compelling romantic comedy that hits all the right notes to be a classic crowd pleaser. The story of two disgruntled singles, each dropped by their partners, has served as fodder for romantic comedies since the slapstick era of the 1930s. In what may be his greatest collaboration with Barrymore, Sandler played another one of his “lovable losers” with the self-deprecating musician Robbie Hart.
“The Wedding Singer” is another film that certainly could not be mistaken for “high art,” but it does have a surprisingly strong hook that relates to the feelings of helplessness that many singles face when they watch all of their friends forming long-term relationships. “The Wedding Singer” exacerbates this tension by putting Robbie in a situation where he is constantly exposed to other people’s happiness, which in turn makes him feel even more insecure.
Sandler has always crushed any opportunities he has to deliver musical numbers, and “The Wedding Singer” serves as a joyous throwback to the 1980s. In fact, the film’s earnest appreciation for the pop singles of the ‘80s predated the wave of nostalgia that became popular in the 21st century thanks to “Ready Player One” and “Stranger Things.”
4. Happy Gilmore (1996)
The best pure comedy of Sandler’s career combined his love of sports with another immature man-child character, even if it toned down the childish shenanigans of “Billy Madison.” While “Happy Gilmore” allowed Sandler to launch into many of his infamous on-screen “meltdowns” (which were a whole lot funnier when they still felt fresh), “Happy Madison” is also an effective sports comedy that uses the same formula that’s been applied in everything from “Slap Shot” to “Major League.”
Of course, the gimmick is that Sandler took the least interesting sport to watch and turned it into an arena for eccentric personalities to take over. Golf may have the reputation of being a meticulous activity that requires precision and patience, but Sandler’s titular character ends up getting a little too invested in victory for his own good.
As with many of Sandler’s comedies, “Happy Gilmore” is able to elevate its straightforward narrative with interesting jokes on the periphery, as there is a strange sense of surrealism that illuminates some of the gags. Cameos in Sandler films can often be quite lazy, but to the credit of “Happy Gilmore,” Bob Barker actually gives a real comedic performance as himself that factors into the plot. The critical divide on “Happy Gilmore” is representative of a generational shift, in which Sandler’s films hit their target demographic. The same could be said for the work of many other ‘90s comic actors who were considered to be Sandler’s contemporaries, including Jim Carrey, Chris Farley, Ben Stiller, Will Ferrell, and Chris Rock.
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3. The Meyerowitz Stories (New and Selected, 2017)
Amidst his deal with Netflix, which featured some of the worst films of his career, Sandler also made an appearance in one of the streamer’s most prestigious projects. Noah Baumbach had been an independent filmmaker of great acclaim, but he took on his most ambitious film to date with “The Meyerowitz Stories (New and Selected),” a generational family dramedy about a group of adult children coping with the legacy of their famous father. Sandler is paired with Elizabeth Marvel and Ben Stiller as his on-screen siblings, with the great Dustin Hoffman as his father.
“The Meyerowitz Stories” tells a story about a dysfunctional clan of relatives who struggle to admit their affection for one another, which actually isn’t that far removed from territory that Sandler has tackled in his comedy films. The difference is that Baumbach offered a very human, emotional role for Sandler, who gives what may be his most vulnerable performance ever. Sandler is often tasked with playing underappreciated characters, but this archetype is more complex when it’s inserted within a high-society examination of New York culture and the inherent narcissism within the artistic community.
Sandler’s affection for his children has been a consistent thread within all of his films, both good and bad, and he shows his ability to play a father thanks to his delightful chemistry with Grace Van Patten, who appears as his teenage daughter. Even if the film ends with a fistfight between Sandler and Stiller, somewhat reminiscent of “Happy Gilmore,” “The Meyerowitz Stories” is one of his only films that would inspire audiences to shed tears.
2. Uncut Gems (2019)
Ever since Sandler infamously passed on a role in Michael Mann’s “Collateral” that ended up going to Jamie Foxx (in an Oscar-nominated performance), his fans had given up on the possibility that he would ever appear in a gritty crime thriller. Even though Sandler had proven to be surprisingly open to working with auteur filmmakers with very distinguished styles, no one could have anticipated that he would choose to star in the latest twisty thriller from Josh and Benny Safdie, a duo known for their transgressive, disturbing style.
Sandler turned Howard Ratner into a thrilling anti-hero, worthy of being ranked alongside Paul Newman in “The Hustler,” Robert De Niro in “Taxi Driver,” or Edward Norton in Fight Club.” Even if Howard is a destructive character who constantly sabotages his own stability, it’s almost impossible not to root for him as he gets himself into deeper trouble.
There’s nothing fake about Howard’s persona in “Uncut Gems,” as Sandler finds truth within a egotistical gambler who only finds comfort in taking risks. There are points in which the tension in “Uncut Gems” is unbearably extreme, but seeing Howard continue to double down on his own mistakes gives the film a wild sense of humor. It’s ironically another immature man-child role for Sandler, even if the stakes are much more grave than “Happy Gilmore” or “Billy Madison.” Joaquin Phoenix may have danced to the Best Actor Oscar the same year for his adequate, albeit overstated performance in “Joker,” but there’s a case to be made that it was Sandler’s wild transformation that deserved the award.
1. Punch-Drunk Love (2002)
There’s no reason to be embarrassed about loving Sandler’s early comedies, as his 1999 film “Big Daddy” found a massive fan in Paul Thomas Anderson, the Academy Award-nominated filmmaker behind masterpieces like “Boogie Nights” and “Magnolia.” Anderson clearly saw something in Sandler that he knew he could lock into, as their collaboration on “Punch-Drunk Love” is among the most unique entries in both of their filmographies.
Even if he’s playing another big-hearted bachelor who is too sensitive for his own good, Sandler had never appeared in a film as strange as “Punch-Drunk Love.” Likewise, Anderson has always had a comedic flair to his films, but his humor reached its apex by the point that Philip Seymour Hoffman is screaming at Sandler over the phone. Existing in a strange place that feels both like a memory and a dream, “Punch-Drunk Love” is a profound odyssey about finding meaning in the absurdities of life.
Although it finds its footing in a story of self-actualization and compassion, there is an anarchic streak to “Punch-Drunk Love” that is exciting in a way that studio films rarely feel. While praised at times and awarded the Best Director prize at the Cannes Film Festival, Anderson rarely got enough credit for the clarity of his vision and its surprising nuance, as “Punch-Drunk Love” is the type of film that improves upon every rewatch. In Sandler’s cast, “Punch-Drunk Love” features such an exceptional performance that it grows infuriating that he has not spent more time making films this good.
