7. Happy Gilmore (1996)
Adam Sandler will always be Happy Gilmore more than he’ll ever be any other character. The slapstick nature of the 90s movie about an ice-hockey-amateur-turned-golf-pro is something that remains funny almost three decades since it came out.
There’s a magnetism to him in the role, a sense of freedom that he’s tried to recapture throughout his acting career, but he’s never truly been able to find it again when it comes to comedy of this kind.
Happy Gilmorehas a staying power that few others have, and Sandler is loved by an entire generation for making this one movie. Despite being so adept at drama, he’ll always be a comedian at heart.
6. Funny People (2009)
The closest Adam Sandler came to making a hybrid comedy-drama that showcased his talents wasFunny People.
Following the story of a famed stand-up comedian who finds out he’s going to die, Sandler’s leading role as George Simmons is one of his most embracing because of how close in nature it is to his own life.
Sandler is himself a stand-up comedian—a very famous one who achieved many accolades for his stage musings—who became a Hollywood actor, so the character of George isn’t too far from his personal experiences.
However, what Sandler does perfectly is draw out a performance that allows him sympathy and disgust in equal measure. He’s not the good guy in every moment of this film, but his tactile sense of life means the audience gets a wholly rounded character.
5. Hustle (2022)
Every time Adam Sandler appears to be suffering a career lull, he comes back with a dramatic performance that reminds us he’s an actor of rare gifts. WithHustle, he became a man who wanted to tell a story about a sport he adores (basketball) through the medium he loves (film).
As basketball scout Stanley Sugerman, Sandler brings across a man on knife’s edge. He’s wrestling with his dream career while fighting against the powers above him to get what he knows he deserves.
InHustle, he takes a shot on a young talent from Spain and decides to house him when no team will take him.
Through Sandler’s rich performance,Hustlebecomes simultaneously intricate and fun, a film with great humor but also great weight behind it, which all comes from Sandler’s role as the leading star.
Related:The Best Basketball Movies of All Time, Ranked
4. Reign Over Me (2007)
Reign Over Meis by far the longest departure Adam Sandler has taken from comedy, as he plays a 9/11 widower who’s left borderline suicidal by the loss of his wife and children.
InReign Over Me, Sandler finds himself deeply immersed in the life of former dentist Charlie Fineman, housing deep anger for what’s been taken under a veneer of life that’s cracking under the weight of his emotion.
None of Sandler’s performances have been as out-and-out heartbreaking as this one, in which he reconnects with his college roommate (Don Cheadle), who helps Charlie get back in touch with the world again.
The brutality of Charlie’s life is laid bare by the magnetic performances of both Sandler and Cheadle, and the audience is left mesmerized by an Adam Sandler they’ve never seen before.
3. The Meyerowitz Stories (2017)
InThe Meyerowitz Stories, Adam Sandler found himself with his old friend Ben Stiller, and from there proceeded to steal every scene.
It’s a testament to Sandler’s very real acting talents that he can outperform even Dustin Hoffman, with the grand sense of who his character is in relation to the rest of the cast.
As Danny Meyerowitz—the unemployed but musically gifted son of Harold (Hoffman)—Sandler takes on the existence of a man who knows he could have done better things with his life. He understands the path he took, and he accepts it as a trait of adult life.
2. Uncut Gems (2019)
Nobody sawUncut Gemscoming. In it, Adam Sandler puts forth a supreme performance as New York City jeweller, Howard Ratner.
Howard is slightly sleazy, highly questionable, yet oddly likable as a leading character. A gambling addict who befriends the type of people you’d never want to meet, Howard’s ambition keeps pushing the stakes of his life higher and higher for those around him.
Sandler operates on a no-quarter-given-nor-received mantra throughout the film, holding the audience captivated through pure adrenaline. We might’ve known Sandler’s earlier work and his capacity to deliver dense work, but few suspected he could transform like Day-Lewis, too.
Related:The Best Movies About Gambling and Casinos, Ranked
1. Punch-Drunk Love (2002)
Working with the greatest filmmaker of the 21st century on his first movie in the 21st century was a challenge that Adam Sandler didn’t fully grasp when Paul Thomas Anderson first called him up.
Punch-Drunk Lovehas been described as “an Adam Sandler movie with consequences.” It’s a film that afforded Sandler the opportunity to play an angry guy with real depth and visceral emotion.
Sandler may have gone on to give wholly different performances in future films, inPunch-Drunk Lovehe showed how much he had to offer the cinematic world, wrought out of him by Anderson’s direction.
The film is a subversive masterpiece of comedy-drama, made by a filmmaker of incredible ability and featuring a leading actor who gave a performance nobody thought he could give.
Read next:Underrated 2000s Romantic Comedy Movies You May Have Missed
