5. The Wedding Singer (1998)
“Billy Madison” and “Happy Gilmore” turned Sandler into a movie star, but even though the latter one is actually now “Fresh” on Rotten Tomatoes, there was still a lot of hate for Sandler among high-brow critics. That’s why they appreciated “The Wedding Singer” much more than his previous efforts because while there are elements of his man-child persona in it, this time the lead character is more of a nice and kind man, a grown-up man in fact.
So they saw some progress in his characters and indeed, “The Wedding Singer” is still one of his best performances because it’s the first time ever he showed his sensitive side as an actor and didn’t rely too much on his usual shtick when it came to comedic moments. Sandler is well known for his humorous songs as a comedian and here he gets to sing, with “Somebody Kill Me Please” being one of the funniest moments of the movie.
Apart from his comedic, dramatic and musical skills, “The Wedding Singer” also gives a chance to him to shine as a romantic leading man. Indeed, he’s surprisingly charming in many sequences. His chemistry with Drew Barrymore is also terrific; they later collaborated in another entertaining, even if not as good “50 First Dates,” and later, one called “Blended” that was unfortunately a failure. The movie is also very good and arguably one of the best “Adam Sandler movies” with its surprisingly sweet moments and lovely nostalgic touches.
4. Reign Over Me (2007)
Sandler had never been this devastating. A top-notch dramatic performance comes at a very surprising time in his career. It came right after “Click,” which had its own dramatic moments, but “Reign Over Me” is probably his saddest hour. The script is not necessarily as strong but Sandler’s performance as a man who lost his wife and daughters on 9/11 and has lived with depression since is so honest and believable that it makes the film engaging. Don Cheadle also shines as his old friend and savior, which turns the movie into an affecting tale of friendship.
Sandler’s humor still exists, which actually saved this film from being borderline depressing. There are several laughs to be had, but they’re not meant to turn the movie into a comedy. They’re just there to give the film a more natural feeling. Even in his comedies, many of his characters have an unstable temperament and a vulnerability that can burst at any moment.
Paul Thomas Anderson was probably the first one to notice that this side of Sandler’s talent would work much better with dramatic material. And in “Reign Over Me,” this side of his is once again used expertly. But don’t think it’s just Sandler in another Sandler role – it’s one of his most different roles for so many reasons, and further proof that he’s actually an actor of range.
3. Punch-Drunk Love (2002)
Profoundly odd, charming, original, touching and different kind of romantic comedy, “Punch-Drunk Love” was the first time where Sandler won the majority of critics, thanks to Paul Thomas Anderson’s sensitive direction and great writing. Even though these days it doesn’t get much mention among Anderson’s best films, “Punch-Drunk Love” is as good as anything by its director. And Sandler is absolutely brilliant in the leading role. Anderson is a fan of Sandler’s comedies and he certainly noticed that he’s got the talent that would fit into his works, and that he deserves better material.
It’s a romantic leading role that functions well on a dramatic level. Sandler plays a man who’s abused by his family, deals with his business, has anger problems, and is searching for love. It’s an eccentric character for sure, but Sandler’s genuine, heartfelt, honest performance makes it interesting and engaging. It also seems to have a very special place in Sandler’s filmography, because every time he appears in a successful “non-Adam Sandler-movie,” the usual praise for him is “his best performance since ‘Punch-Drunk Love’.”
Maybe it’s the fact that this was the first time he impressed his skeptics, or maybe his other dramatic work isn’t as popular, who knows. But it shows that even some of his haters can’t deny the power of his performance in this unpredictable and beautiful film. “Punch-Drunk Love” remains as his only Golden Globe nomination to date.
2. Uncut Gems (2019)
The Safdie brothers keep doing great work in independent cinema, and it seems “Good Time” managed to bring them to the attention of even wider audiences. There was considerable hype for their next feature and it was obvious that if they got Sandler for the lead role, they would have a meaty role for him as they had for Pattinson in “Good Time.” And indeed, Sandler is brilliant.
Most of his dramatic work was usually him portraying nice guys, so it’s refreshing to see him playing a man who is this corrupted by his own greed. He cheats on his wife, he’s a neglectful father, and he’s greedy like no one else. He never played a character like this and he’s so great that it will certainly win over some of his haters as well. While we don’t necessarily root for him, we’re interested in what he’s up to and that’s mostly because of Sandler’s layered, impressive work.
So many things happen in the film and the tension almost never stops, and Sandler is in almost every frame of the movie; it’s great to watch his totally committed, charismatic and complex work. This year, it’s the first time that Sandler has been nominated and won awards from critics groups, and he won a National Board of Review award for Best Actor. All the praise for him is so well-deserved, and hopefully his success here will motivate him to get better roles instead of wasting his talent in another lazy Netflix comedy.
1. The Meyerowitz Stories (2017)
Maybe seeing Adam Sandler’s name and the word “Netflix” in the same sentence doesn’t give a good feeling, but this is not a Happy Madison picture – it’s a Noah Baumbach movie that premiered in Cannes, the second Sandler movie to do so after “Punch-Drunk Love.” It just happened to find a distributor in Netflix. Baumbach has been working for more than two decades, consistently delivering great work. Some of his material may not appeal to everyone, but he has been embraced by critics for so long and this year with “Marriage Story” he finally got a lot of industry recognition as well.
“The Meyerowitz Stories” is one of his best films, one of his most acclaimed and one that certainly deserved more awards recognition, especially for Sandler’s brilliant performance. The movie follows an estranged family’s gathering together in New York City for an event celebrating the artistic work of their father; while Ben Stiller and Dustin Hoffman both deliver terrific work as well, the movie is still Sandler’s show. He is somewhat of an emotional core of the movie. His character Danny is a disappointment to his father; he’s just divorced and he doesn’t know how to be a supportive father. He’s going through an identity crisis.
As usual, there are elements of his trademark traits; the goofy voice and sudden outbursts, for example. But his physical comedy works amazingly well here, it never feels out of character or unrealistic. However, it’s not exactly a comedic performance; Danny might be his most complex character to date and he plays him with such sensitivity and care. He displays a certain vulnerability in many scenes, which is just remarkable. When he sits down with his daughter at the piano and starts to sing, the result is just lovely. There’s no overacting, and in fact, his performance might be the thing that stays with you most when the movie ends. Pity that his performance here didn’t get much buzz. It very well can be his best work to date.
Honorable Mentions: Voice work in “Hotel Transylvania”; his dramatic attempt in “The Cobbler”; and if you like his type of humour, most of his comedies between 1995-2006. Special shoutout to less-known buddy comedy “Bulletproof.”