The Take-It-Easy Ballad of Adam Sandler, World’s Most Interesting Actor
Now when I’m on a diet, you take away my potatoes. Say “fuck those guys” after reading Rotten Tomatoes.
That is one of the more career-relevant lyrics from the final song in Adam Sandler’s 2018 Netflix stand-up comedy special, Adam Sandler: 100% Fresh. Much of this song is just about Sandler’s love and marriage, but it transitions at the end as a montage of his career plays on a screen overhead and Sandler thanks his fans for “getting old with him.” The song is written as a tribute to his wife, Jackie Sandler, and it is a much happier reflection on a love in life than the song it succeeds, the one about Chris Farley.
You finish wiping away those Farley tears only to have a bit of a nostalgic bout of sadness when you see how much of Sandler’s career has elapsed already. I remember watching the stand-up special and thinking it was classic Sandler type humor. It was his good kind of humor and charm like one of his SNL characters, Opera Man. But then those last two songs just take it to the next level. Never thought Sandler could make me feel things in that way, but there I was, marveling at a Netflix special I never would have guessed would be good. That’s the fault of my own prejudice. (And I count myself among Sandler’s more forgiving fans.)
I thought he was maybe retiring or something after watching the montage of his film and television roles as he crooned, “Thanks for growing old with me.” I kept thinking, Was he saying goodbye to us? Is that Sandler’s swan song?
Of course, a fair bit of research was more than enough to illuminate me that he was, in fact, not retiring. There were still two movies left on his deal with Netflix (before the streaming service surely extends the contract) and he was also filming a movie called Uncut Gems, directed by Josh and Benny Safdie.
At first, that did not mean a lot to me, but then I learned that the Safdies have been hailed as some of the best up-and-coming directors in the film industry and I got really excited about the prospect of Uncut Gems. Most of the time, Sandler works with directors he is good friends with and it results in movies that feel lacking, to put it kindly. But when he works with directors that have true visions and want to try something new, daring, and original, he is really special.
Of course, I’m not really saying anything new here. I’ve long known Sandler to be an amazing actor who chooses to phone it in and have fun in tropical destinations with his best friends for millions of dollars instead of really pushing himself as an artist (wouldn’t you?). Everyone knows that. It’s a common refrain in the Sandler-themed discourse that peppers the culture at some point every year.
But I wanted to push my own thoughts about Sandler further, in the same way I root for him to pursue higher career peaks. It was a perfect confluence that led me back to the Sandler path at this current point in time, too.
Growing up, I was a massive fan of his movies. When I first got into sports, I discovered Happy Gilmore on cable and, as a golf enthusiast, I was just blown away by how much I enjoyed it. I still remember walking into my local movie theater with my family and seeing the poster for Grown Ups (which now hangs on my wall. I know, I know) for the first time and thinking, Holy shit. It was like The Avengers (a movie that did not exist in 2010) for comedy stars. Low-brow comedy stars, sure, but when you’re twelve years old, they’re your comedy heroes.
I was into Kevin James and David Spade more back then, because I also enjoyed their turns in Paul Blart: Mall Cop and The Emperor’s New Groove, respectively, and neither of those films had anything to do with Sandler. Back then, I understood that Sandler was the ringleader (his circus includes more than just the Grown Ups stars. It also features former SNL mates, sports icons, and 1980s has-been celebrities, among others), but he wasn’t my favorite. (As for Chris Rock, I was too young to realize he was maybe slumming it in Grown Ups, but enjoying himself nonetheless. Rob Schneider, however, I was much less enthused by.) And while Spade can be an excellent storyteller, neither of them have done anything that has impressed me a much as what I’ve uncovered from journeying down the Sandler rabbit hole.
That journey is a lifelong one. I’ve been on it for over a decade now and only after that period of time do I finally feel comfortable to attempt to tackle my concept of Sandler, which I thought was too undeniably bold to actually pursue at length in a written format. But like I said, a confluence happened.
On the heels of Sandler’s Netflix special and his Emmy-winning return to Saturday Night Live, I happened to decide to watch 50 First Dates with my family. Now, 50 First Dates is one of my top movies of all-time and I hold it very dear to my heart, but I just couldn’t help but notice how struck I was by the film’s charms. Even after watching it for the fifth or sixth time, all I could think was, I could watch this every day and never get sick of it.
Why was that? I know I love the movie, which would be traditionally seen as a guilty pleasure. But I never have connected too deeply with Sandler’s sense of humor. Dozens of comedians would rank above him in terms of how they’ve made me laugh, but still I return to him and 50. Maybe it’s because they feel like old friends. But maybe it’s because Sandler can turn on charm like no other actor can. Compared to what first impressions would lead one to believe about Sandler and I cannot help but think the disparity between those impressions and the heights to which his charms can reach are greater than any other actor.
So I decided to dig deeper, in anticipation of Uncut Gems and in the experience of having a “Sandler moment,” as it were. And I watched Reign Over Me. And in the famous emotional breakdown scene, I had one thought that was rattling around in my brain, demanding to be released onto this website now.
When he wants to be, Adam Sandler is the greatest actor alive.
I know many will disagree with this, perhaps vehemently, but all I could think during that scene from Reign Over Me was, How does he do it? How does he flip that switch and become something truly unique and special in the world of movies?
I wrote a whole outline for an essay about that, but it seemed too sprawling to click into place for me. And I know I do this a lot, but I genuinely think that the best way to write about what makes Sandler so special as an actor is to rank his performances. That’s the best way to talk about him. At least, that’s what I’ve found.
Even in the panned projects, Sandler is always going for something. It may seem lazy, but that line I quoted above about Rotten Tomatoes seems pointed and distinctly intentional. I think, even when we perceive him to be bullshitting his way to a paycheck (and, hey, I get it. Sandler has said before that he makes an artistic feat of a movie and it bombs at the box office and then he makes a raunchy, lame comedy and it makes hundreds of millions of dollars. What is a man to do?), he is always going for it. His wife reassures him that the critics of Rotten Tomatoes don’t know what they’re talking about. Why would she if he didn’t care? He does care. He’s not actually phoning it in. He’s just taking it easy.
You don’t get to be the world’s most interesting actor without having immense talent. Sandler has that in spades. So maybe it just looks so effortless when he’s trying to be funny that we perceive it to be truly devoid of effort.
Or maybe every movie he stars in is a brick in the massive castle of the Sandler comedy legend that he dismantles whenever he makes something truly thought-provoking. Is it all just a bait and switch?
Tons of directors are deft at using an actor’s persona to challenge the audience in a new film that stars said actor. But few actors are able to do this, too. Sandler is one of them. From what I’ve heard about Gems, Sandler is pulling from decades of public perception and a comedy wheelhouse that turn his performance into something that is not only Oscar-worthy, but meditative, unhinged, and the embodiment of that Netflix montage of his career.
After all, I think about the fact that Sandler was supposed to be The Bear Jew in Inglourious Basterds every single day of my life. It is the greatest missed opportunity I can imagine in all of film history. I pray something like that remains in his future.
And I’m excited about his future. Beyond Gems, what else will Sandler do for us (or, to us)? I’m so curious to know, just as I was extremely intrigued about who he is. As a person, as an actor, as an icon. And I was intrigued (and still am) about who he wants to be. And that is why I embarked on the 2019 Summer Sandler-thon. Every major leading turn from Sandler that I had not yet seen went into my Letterboxd watchlist. And I began.
36. Jack and Jill Sadelstein in Jack and Jill
I can’t make any excuses for Jack and Jill, however. This is one movie where Sandler is playing two characters, the titular siblings, but neither performance is winning. Often panned as one of the worst movies of all-time, I completely get it. It’s what I see as the low point in Sandler’s career and one of two movies I learned nothing about him from when I revisited it.
35. Donald in Zookeeper
This is the other one, but it seems less because Sandler didn’t really give a shit and more that it is just a minor role that he did for a friend. Zookeeper is Kevin James’ vehicle through and through, but it is still a Happy Madison production and, as such, Sandler did a favor for his buddy by voicing a nonessential monkey in the film.
34. Chuck Levine in I Now Pronounce You Chuck & Larry
This is the worst Sandler movie to actually teach me something about him and I think it is that he is a good friend. The movie is not great, in so many ways, and it is definitely a product of its 2007 release year. But, at the core of it, I think Sandler just really liked hanging out with James and he wanted to make a movie with him. That’s a crucial piece of the Sandler mythology: his friendships. A lot of the choices he makes are because of the people he wants to spend time with. The character of Chuck, though, was completely forgettable and Sandler’s performance did nothing to help that.
33. Donny Berger in That’s My Boy
Donny Berger is another character that would be extremely problematic if he existed in a Sandler movie that came out in 2019. Aside from that aspect of Sandler’s turn, he is also incredibly abrasive, obnoxious, cartoonish, and putting on a horrid Boston accent. But That’s My Boy taught me that Sandler knows his legacy as a comedian. It might not necessarily be an all-too-humorous legacy, but his influence was definitely felt in the early comedic style of Andy Samberg. Obviously, Samberg has evolved way past that Sandler-esque SNL type, but he also really wanted to work with Sandler because of how influenced he was by him growing up. The two even collaborated on a sketch for the SNL 40 special. Sandler’s legacy is immense and he has influenced an entire generation of comedians, for better and for worse.
32. Nicky in Little Nicky
Little Nicky is one of the last gasps from the era of Sandler’s comedies when his hits were named after the main characters he played. (In my mind, this includes Billy Madison, Happy Gilmore, The Waterboy, Little Nicky, and Mr. Deeds.) Of those films, Little Nicky was definitely the worst and one of the first signs that Sandler could bomb harder than any average bomb. His voice is grating and the humor is borderline offensive. But after a string of massive box office successes, Little Nicky was the product of Sandler being allowed by the studio to make anything he wanted. It’s not funny or good, but it’s about the son of Satan embarking on an Earth-bound adventure. So, at least he was trying something different. That’s the thing about Sandler, he seems interested in playing with different genres and concepts, even if a lot of the story beats and points of dialogue remain similar.
31. Carmine Weiner in Coneheads
When you are embarking on a Sandler-themed cinematic quest, Coneheads is definitely one of the most inessential installments. Founded on a sketch from the pre-Sandler days of SNL, Coneheads is a miss from a comedy standpoint, but very interesting from the perspective of it being used as a massive hybrid between two eras of SNL. Jane Curtin and Dan Aykroyd hobnobbing with Sandler and David Spade, among others, showed the cultural, generational reach of SNL and it was undoubtedly an influence on Sandler inserting buddies and actors of similar experiences into his movies. He plays a bit role in Coneheads, but it might have been a crucial piece of the puzzle when he began to figure out what his film career was going to look like after he was fired from the NBC sketch comedy show based out of 30 Rock.
30. Lenny Feder in Grown Ups 2
Grown Ups 2 is the epitome of the “Sandler chills with his buddies” type of movie. The first Grown Ups, I’ll always have a soft spot for. And at least, in that one, there was a beating heart behind it, reminiscent of Sandler’s early days when the comedies he made were dumb, but sweet. In Grown Ups 2, however, we might as well just be watching the dream version of what a day in the life of Sandler would be like. Having never done a sequel before, it was clear that Sandler was here for the money. And, I mean, if I was paid millions to hang out and have fun with my friends, I bet I’d say the same thing he did.
29. Tommy “White Knife” Stockburn in The Ridiculous 6
Sandler’s first pivot into Netflix-exclusive comedies came in 2015 with the panned western comedy, The Ridiculous 6, an obvious attempt at a send-up of a genre that seems hellbent on pairing adjectives with numbers. He really chose the perfect time to transition his career into streaming. At a time when comedies are consistently failing at the box office, it seemed thoroughly unlikely that Sandler would be able to weather it. (The highest grossing comedy of 2019 domestically is The Upside with $108,252,517. Comparatively Grown Ups 2 netted $133,668,525 and wasn’t even in the top twenty domestically for 2013.) On Netflix, though, his films are on-demand instead of in a theater where people would have to make the conscious decision to pay for them. His aloof, psuedo-physical performance as “White Knife” was heavily derided, but it was interesting, at least, to see what Sandler thought cowboys were.
28. Adam Sandler in Top Five
Sandler has done a lot of favors for friends over the years (even though he probably doesn’t consider them to be favors), but it was interesting to see one of his buddies take on a project of his own. Because then, we got to see Sandler in the role of a cameo instead. Chris Rock’s 2014 passion project, Top Five, was nuanced and thoughtful, even if if didn’t always hit the mark. What it did hit, though, was in the capacity for actors to appear as themselves. Sandler gave one of the more surprising turns in a subdued role that showed he did not always need to be a lead to be funny.
27. Max Kessler in The Do-Over
My current theory about Sandler’s Netflix tenure is that he is trying to bang out the genres he had not done yet thanks to the freedom of the service to make whatever he wanted with the knowledge it was guaranteed to be a massive hit. Obviously, The Ridiculous 6 was a western, The Week Of was a mockumentary, Sandy Wexler is a pseudo-biopic, Murder Mystery is obviously a crime mystery, and this one, The Do-Over, is an action movie. (The upcoming Hubie Halloween could be a chance at Sandler doing horror. Can’t wait to see his take on the war genre.)
But yes, in The Do-Over, Sandler is doing his best attempt at being an action hero who is supposed to come off very cool. It’s not easy to buy, but he gets to spend time with David Spade and I like the fact that they’re still friends. Not that there’s any reason they wouldn’t be, but it’s refreshing sometimes to see friends be friends in Hollywood.
26. Davey Stone in Eight Crazy Nights
Eight Crazy Nights is a baffling movie for a number of reasons. Like, why did it have to be animated? I don’t know. Regardless, it is Sandler’s first major foray into animation in his career and, even though it’s not very good, you cannot tell the story of Sandler without writing about his strong connection to Hanukkah. “The Chanukah Song” is a signature Sandler tune and one of my all-time favorite bits of his. Eight Crazy Nights takes this holiday attachment to new commercial heights and new critical lows, but Sandler obviously has a very distinctive voice that can translate fairly well to a vocal medium.
25. Billy Madison in Billy Madison
Billy Madison was the first breakout success for Sandler (though, it did not stop him from being fired by Lorne Michaels) and it is the performance that Sandler has said is most similar to himself. I find a hard time believing this, simply because I don’t think Sandler is that much of a man-child (almost literally). I know many regard it as a comedy classic, but I never had the patience for the performance which is riddled with rage explosions and general idiocy. Fair enough to all who like it, but I think Sandler honed his cinematic sensibilities better as his career began to blossom.
24. Sam Brenner in Pixels
At first glance, this might seem like an extremely forgettable installment on the list. And to many, it probably will be. But when I started to evaluate Pixels as less of an Adam Sandler comedy and more of a children’s movie, it really all fell into place. Sandler was giving a performance that you would be more likely to see from someone like Eddie Murphy or Mike Myers during the early 2000s. Instead, he rolled it out in 2015 and I can only imagine he was playing a character that he would have looked up to himself as a video game-loving kid and teenager in the 1970s and early 1980s.
Also notable about Pixels is that, aside from the Hotel Transylvania series, it is the last movie to be released in theaters by Sandler. Of course, Uncut Gems will remedy that in the U.S., but if this is the last big screen comedy we see from him, it is a disappointing note to go out on all the same. The one thing Sandler never truly was, was the every-man.
23. Sonny Koufax in Big Daddy
Big Daddy was, at least in term of Sandler’s comedies, the last instance we see of him keeping it low-key. The 1999 comedy with Dylan and Cole Sprouse was the last film of his before the Happy Madison production company allowed him to basically do whatever he wanted and make bank for it. But this performance is one that lands on the winning side of things because we see Sandler working to impress in a non-Happy funded project. He also rolls out the charm that he typically reserves for rom-coms. Any one of these charming performances will come with its fair share of juvenile humor, but for some reason, it never sticks to him. You can still buy him as a lovable guy despite all the flaws because there is something within Sandler’s demeanor that is unmistakably sincere.
22. Zohan Dvir in You Don’t Mess with the Zohan
Speaking of roles that Mike Myers probably would have played, wow! Zohan definitely plays like any other Sandler studio comedy, but the character himself is unlike anything he ever portrayed, for better and for worse. For the most part, Sandler plays a generic character with some boilerplate name and we move on with our lives after thinking of the performance as Sandler playing himself rather than Sandler playing “Dave” or “Paul” or whoever. Zohan, though, is absolutely a choice. It is a movie that seems to have been created all around the character, which is a wacky role that somehow fell to Sandler in 2008. He doesn’t do a whole lot of great things with it, but he makes it watchable, which is more than I can say for what the Jon Heder (or whoever) version of this would have looked like.
21. Paul “Wrecking” Crewe in The Longest Yard
Remaking The Longest Yard and casting yourself in the Burt Reynolds role is certainly a bold move, but it is not the boldest remake that Sandler ever did (more on that later). Directed by Peter Segal, I think there is something special about how Sandler plays this one, thanks to Segal. For the most part, Sandler works with directors who execute the vision that the “Sandman” had for the comedy. Obviously, when he works with prestige directors, they know how to play to his strengths better than anyone. But hiring Segal is a good way of splitting the difference.
In my mind, Segal has only made one movie that I truly love, 50 First Dates, but none of the other movies he’s made have been out and out “bad.” They always have some sort of redeeming quality as Segal finds the ability to turn something that probably has a good shot of being lame into something cute and, at the very least, heartfelt.
Sandler plays on the perceptions of The Waterboy in The Longest Yard, to be sure, but he also tries to be the cool leading man. Thanks to Segal’s direction, it always seems to be just properly undercut. It’s still a Sandler comedy, but it has the vibe of something weightier because of that.
20. Dracula in Hotel Transylvania
While Sandler’s performance as Dracula is much less interesting than Wrecking Crewe, I had to give it the edge because of how much in his wheelhouse it is. And, to be honest, if no one else was going to do anything with these properties, why not turn it into an animated film series for kids?
I only felt the need to see the first installment in this trilogy, but by all accounts, it is a cut above Sandler’s usual fare. As for the first one, it was a charming watch that did not necessitate a rewatch, but made for a fun October memory. It’s also rather impressive that they turned the look of Dracula into one that would resemble Sandler. He knows we need that familiarity, no matter the age bracket we fall into.
19. Nick Spitz in Murder Mystery
Recently, this tweet about Sandler and Murder Mystery went viral.
And there’s hardly much more to say it than that. Murder Mystery, by most metrics, is not a good movie. But it is vastly more entertaining than his alternative Netflix output. Whether that’s because of James Vanderbilt’s script or because there is a genuinely interesting mystery at the heart of it, I’m not sure. But Sandler’s laid back attitude has rarely been this welcome in the 2010s. The laziness with which he portrays himself as Hercule Poirot (basically just a mustache) is almost forgiven by the film’s nature. His poking holes in everything going on around him is quite enjoyable and has made for a lukewarm, unsatisfying appetizer for his other 2019 film.
18. Skeeter Bronson in Bedtime Stories
Technically, The Waterboy is a Disney movie that Sandler starred in because of the film’s position under the then-owned-by-Disney Touchstone Pictures. But we know that hardly counts and, in that sense, Bedtime Stories is the only true Disney movie Sandler has ever been involved in. It’s odd because, many perceptions of Sandler are rooted in how he just makes lame comedies for seven to ten year olds. But his actual movies have had that juvenile sense with a touch of raunchiness. He’s largely been an R-rated guy until it seemed like he was making movies that his kids could see.
And in that sense, Bedtime Stories succeeds. The Disneyfication of a classic Sandler story brings it a requisite sense of whimsy and cuteness, but it is ultimately another example of the down-on-his-luck, trying-to-be-a-good-father character that Sandler leaned into heavily as the 2000s barreled forward. He sells it well, but never in the sense where you get the feeling that Sandler’s kids would actually be that against him.
17. Danny Maccabee in Just Go with It
One of the strongest factions of Sandler’s career is his rom-com department. Arguably, he is never better than when he is paired up with Drew Barrymore (notice that none of those have appeared yet on the list), which is why I dropped Just Go with It into the seventeenth position, even though he is still nailing all the romantic elements that I pride him on.
For the most part, I think this is due to his chemistry with Jennifer Aniston, which is fine, but she is definitely no Drew. It’s the Hawaiian setting all over again, too, which Sandler obviously thrives in, as any of us would. I appreciate it in the sense that it gives a pale imitation of 50 First Dates, but I cannot help but be easily charmed by Hawaiian rom-coms. I’m a sucker, I know.
He’s not even doing anything particularly special in the movie, he’s just being himself with an extra dosage of sweetness. And yet, I buy into his rom-com persona so heavily that it all clicks into place as soon as the plane touches down on the island.
Additionally notable about Just Go with It, which was a box office behemoth ($215 million!) that would not experience the same success today, is the pairing of Sandler with not just Aniston, but also Brooklyn Decker. A common criticism of Sandler is that he is always with women way out of his league in movies. This might be the most egregious example of that. I’m just glad he’s not a dick about it.
16. Dave Buznik in Anger Management
One of the hallmarks of a classic Sandler performance is his ability to flip a switch from mild-mannered to rage-coursing-through-his-veins in an instant. Paul Thomas Anderson knew how to harness that. It seems like the Safdies have mastered it, too.
But put Sandler in a comedy all about his anger and you know it’s going to be an hour and a half of unchecked screaming that could get on your nerves in an instant. Not quite with Anger Management, however, as the aforementioned Segal subverts that very expectation by pitting Sandler against one of the best living actors, Jack Nicholson. Sandler is obviously a strong performer, but one of the best bits of evidence for this early on in his career was his ability go toe to toe with Nicholson and appear unflappable about it. As if he’d never heard of The Shining before. He compartmentalized and stayed true to his comedic vision and it worked and it showed, even if the film, as a whole, is not the best showcase for either performer.
15. Don Truby in Men, Women & Children
During the late-2000s and early-2010s critical swoon of Sandler’s career, it seemed as if he had truly thrown in the towel. Reign Over Me and Funny People had just garnered him raves, but his comedies were making more money than ever. So he stuck with them for a while. In 2014, he came back to what we love with a pair of performances (including the one listed below) that stole the show from otherwise middling movies.
Jason Reitman’s Men, Women & Children was initially poised as an awards contender, but quickly sank under the weight of poorly-written scenes and an overall sense of the story being an eye-rolling affair. But Sandler was always the most engaging part of it. And he doesn’t look half bad with a beard.
Regarding Sandler’s casting, Reitman said the following to IndieWire’s Drew Taylor: “He had so many interesting things to say, and his questions were great, and then finally he would come as prepared as any actor I’ve ever worked with. He knew the scenes in the screenplay as well as he knew the scenes in the book. He’d bring up little moments in the book and say, ‘do you think we should be doing that beat?’ And they were never done for selfish reasons and were all really smart, thoughtful points, and it was just a pleasure.” Sandler’s a smart guy.
14. Max Simkin in The Cobbler
Also in 2014 came The Cobbler, which was put to screen by Tom McCarthy, who would win the Best Picture award for Spotlight in the following year. But The Cobbler was a film that vastly underperformed and it really left me wanting more from Sandler, staunchly hoping that he wouldn’t give up genuinely moving performances just because two of them came in panned films. Plus, The Cobbler was ambitious and that can’t always work. Can we at least give it and Sandler points for trying? It’s nice to see the effort.
13. Bobby Boucher in The Waterboy
I think Happy Gilmore is Sandler’s best out and out comedy and, in terms of the sensibility of that movie where it blends a sports concept with an extremely well-defined character who inspires the love and heart of a community while having some schlocky laughs along the way, The Waterboy matches up the closest with it.
Few characters come as fully formed and memorable as Bobby Boucher does from the first seconds he’s on screen in The Waterboy. Yes, Sandler is doing another annoying voice, but there is something simple and wonderful about the fact that we are able to understand exactly what Bobby Boucher’s biggest fear in the world is after only having known him for a half hour. It was a remarkable execution of character on Sandler’s part.
12. Jim Friedman in Blended
Jim Friedman is definitely a character who has not entered the cultural lexicon in the way that Bobby Boucher has. But that does not make his performance worse. In fact, I was really intrigued by the way Sandler was able to pull off a divorced hermit who wants nothing to do with the world or its love, especially since his home life seems to be in direct contrast to such a notion.
Again, though, I have to return to the winning formula that is Sandler and Barrymore in a cool location as they fall in love. To all who say they never buy them together, I disagree vehemently. Yes, she’s beautiful and yes, he’s Sandler, but again, it’s the charm. I completely buy into them falling in love because of how much fun it would be to spend time with him. He knows that, too, and he uses it to show how sweet and loving he can be around his friends and around those he is romantically interested in.
The character is not as fully formed as Bobby Boucher, but Jim Friedman is far more nuanced.
11. Lenny Feder in Grown Ups
Grown Ups is a ceremonial passing of the torch for comedy movies. Now, Sandler has continued to make comedies and there is no one actually in this movie who he passes the torch to anyway, but it feels that way all the same.
Sports is a major focus of the story as the quintet are united by their love and history of basketball together. And the story of this movie and its marketing was the same sort of, “Sandler’s never thrown a cast together like this before!” diatribe you’ve always heard. But this time it was real because he allowed it to be an ensemble instead of a two-hander or a solo outing. The cameos remained, but all five of the stars (Sandler, James, Rock, Spade, and Schneider) had real character arcs and roles to play.
But throughout the movie, we get the sense that Sandler is learning. That he’s ready to move on from the kinds of movies that made him the star he is. He’s not passing the torch to anyone in particular, but he is stepping aside from the comedy spotlight, allowing himself to still star in comedies, but no longer starring in the biggest ones of the year.
When he misses that bank shot, we see Sandler as we never have before. Content to let someone else have the glory. Content to lose. Content to just be loved by those who love him, because sometimes that can be enough.
10. Longfellow Deeds in Mr. Deeds
You would have never seen Gary Cooper wearing t-shirts, but maybe that’s why Mr. Deeds was remade. The “every man” concept changed over the course of seventy years and a Sandler type “schlub” was more aligned with the person you’d run into in a small town and get to know than some man who was constantly wearing a suits.
What elevated Mr. Deeds for me is that it is a script where most of the jokes have some layer of absurdity to them rather than just being gross-out or shock value jokes. Something about Sandler’s fit into a role like that just feels more natural and pleasant. Like he’s working in his wheelhouse and it’s actually clicking. Cooper could never.
9. Michael Newman in Click
The first half of Click is exactly what you’d expect from Sandler, even down to the point when he uses the universal remote to put a jogging woman into slow motion. It’s a scene that was probably good for about eight percent of audiences, but for the rest of us, all we could do was roll our eyes. And roll them I did, considering this is the only movie I owned that could be played on the old PSP video game console.
But then, the second half of the movie actually decides to call Sandler’s dramatic chops into play, resulting in an absolutely gut-wrenching climax in the rain, unlike anything you ever thought he could bring to a comedy. There are still people probably absolutely flabbergasted that Click actually “went there.” Of course, it shied away in the end, but that doesn’t mean Sandler’s performance was any less real.
If he was channeling shades of Cooper in Mr. Deeds, then there is no denying that Jimmy Stewart was a major influence on Sandler here.
8. Robbie Hart in The Wedding Singer
Probably the sweetest role of Adam Sandler’s filmography. It’s so sweet, in fact, that you actually can, albeit very sparingly, forget that it is the Sandman in the role. It’s a Herculean effort to do that with a Sandler movie, but there are moments when he just is Robbie Hart. I don’t know, maybe the hair helps.
Regardless, this was his first rom-com pairing with Drew Barrymore and it still ranks among his most beloved and culturally impactful movies. The climactic airplane scene is a big deal still that has been recreated in a number of movies and shows. And Sandler shows that he actually has some good singing chops that are not entirely reliant on him doing goofy voices during the middle of his songs.
It’s a sweet, tender, fun movie led by a performance that just might trick you into thinking he’s a heartthrob. It’s still impressive to see Sandler lean into that side of himself so early in his career. Doing this movie is one of the smartest moves he ever made.
7. John Clasky in Spanglish
What is special about Sandler’s turn in James L. Brooks’ Spanglish is that he is billed as the lead of the film, but he is hardly the heart of the story in any way. For the latter half of the film, he settles into a supporting role as we see the relationship between Cristina and Flor Moreno unfold. Too often, single story narratives are depicted on screen, but Spanglish bucks that tradition by having the Mexican mother and daughter as the beating heart of a movie that is, at its core, about that relationship. It rounds out into something quite special because of that focus.
As such, Sandler steps to the side. He doesn’t invoke his myriad techniques for dominating a movie or making it into a quintessential Sandler comedy. He plays his part to perfection and bounces off the actors flawlessly. He is charming without being juvenile, sweet without being burdened. He ended up being the perfect choice for Claksy.
6. Danny Meyerowitz in The Meyerowitz Stories (New and Selected)
I’ve never been the biggest fan of Noah Baumbach’s movies, so when I heard this was coming to Netflix, I only decided to watch it because Sandler and Ben Stiller were playing brothers and I expected I could derive value from watching my childhood comedy heroes act in a drama together. My expectations were still low and I anticipated another dramatic Sandler misfire like The Cobbler or Men, Women & Children, but it turned out that Baumbach was much more deft at handling Sandler than McCarthy or Reitman. It became my favorite Baumbach film, largely because of Sandler’s scene-stealing performance. More directors should take him seriously as someone who can elevate a movie because The Meyerowitz Stories would not be special without him.
5. George Simmons in Funny People
Many Adam Sandler performances borrow from the actor’s iconic roles, harnessing his anger and his fastidiousness, as much as the rom-coms utilize his charm. But only Funny People, directed by Judd Apatow, uses Sandler’s persona as a comedy legend and turns that on its head, resulting in a pained, subdued role. He chose this over Inglourious Basterds, which hurts, but he also turns in a career best role, so you can’t get too mad about it. His restrained pathos makes you think he’s channeling from a lot of past memories that can still cause pain. The idealized notion of comedy, systematically broken down by Sandler with every utterance under his breath and every turn away from a friend with his body language. As much as Apatow has an eye for a perfect role, Sandler has an eye for exactly what Apatow would want. The stories of Sandler being a nice guy in Hollywood are apparent here as he is more than happy to be Apatow’s muse.
4. Happy Gilmore in Happy Gilmore
Happy Gilmore is the best straight comedy movie Sandler ever made and his performance as Happy, utilizing rage more than any other, is one of the best comedic character creations of all-time. It’s hard to overstate how perfect every one of Sandler’s line deliveries is. “You’re gonna die, clown!” is always in my memory.
There’s really not much else to say about Happy Gilmore aside from the fact that it has been one of the biggest influences on Sandler’s career, from the directors who found something to love in it to its references in other Sandler movies (golfing in 50 First Dates, Chubbs in Little Nicky, etc.). As solid, funny, and tightly-constructed as any comedy performance you’ll ever see.
3. Henry Roth in 50 First Dates
50 First Dates is not only my favorite Adam Sandler, there is a legitimate chance that it is one of my ten favorite movies ever made. There’s some classic Sandler problems in it, I know, but I just cannot get over the way it makes me feel. So happy, so charmed, so in love, so deliriously running on the fumes of joy that come from Hawaii, rom-coms, Drew Barrymore, Sandler, and the fact that they do not come up with some deus ex machina. They commit to the story they wanted to tell and it pays off a thousand percent.
Sandler crying on the boat while listening to The Beach Boys is about as good a needle drop you’ll find in a comedy and he channels all sorts of comedic skills he’s learned over the years while trying to woo Barrymore. He sings, he screams, he cries, he laughs, he sticks a toothpick in a waffle. It’s all positively lovely.
Much of the success for Sandler in 50 also largely comes from how Barrymore gets so much to work with in the movie. She is a perfect foil for him and they both bring out the best in each other. Can’t wait for 2024.
So much love for this movie and this performance, but he has two better performances, I think.
2. Charlie Fineman in Reign Over Me
This is the performance that set me off on this two month long Sandler excursion. I remember watching the scene in Reign Over Me when Sandler finally has his emotional breakthrough and just staring with my mouth agape, thinking, Holy shit, this is legitimately the best actor alive right now. I couldn’t believe it. He wasn’t using a persona or playing on past notions of himself. He was just being Charlie Fineman and allowing himself to feel every raw emotion someone in his condition (and I won’t spoil what that condition is) would have. Anytime he was on screen, I could not stop watching. I wanted to rewind every scene and watch his hands and then watch his face and then just close my eyes and listen to his dialogue. It’s weird, but I was completely wrapped up in the idea that Sandler could deliver something so heartbreaking. It still blows my mind.
1. Barry Egan in Punch-Drunk Love
Yes, it’s still Punch-Drunk Love. I hope Sandler’s career did not experience its apex in 2002, but for the time being, it seems like it has. (Uncut Gems, please.) Not that there’s anything wrong with that, of course. This is not an easy movie to top. Paul Thomas Anderson understands Sandler on every level. I fully believe that. PTA, who does not wish to overlook any movie, has always had a penchant for watching and enjoying Sandler’s comedies and it’s how this pairing came to be.
The pseudo-Superman figure portrayed by Sandler with a strong backdrop of mental illness is out of this world. He radiates with punchiness and a frenetic to-do list every time he’s on screen, until he finally lets go of responsibility and turns on the love, letting go of all restraint and restrictions before pursuing what he wants most. He goes toe to toe with some of the best actors at the time and even circles Philip Seymour Hoffman, topping him entirely.
From the first second on screen, Sandler dominates Punch-Drunk Love and he doesn’t let go until the throttle finally has a chance to be released. White-knuckled clutching is felt in every hazy step-back and sentence cut-off by another “loved” one. The breaking point is always just around the corner. It’s a shame Adrien Brody won the Oscar for The Pianist when Sandler wasn’t even nominated. It’s one of the greatest performances of all-time because of how much Sandler is doing in it and how much he is still holding back. I don’t quite understand Sandler, the man, but this 2002 classic helps me understand Sandler, the performer.
In summation, I am not sure I actually have anything particularly original or interesting to say about Adam Sandler. The idea that he is a gifted actor who decides to kick back with his friends is a time-honored notion that has been repeated so often it has pretty much seeped into the cultural textbook as fact.
But there’s something noble in Sandler’s non-pursuit. In an age where so many actors are eager to shed the personas, roles, and sensibilities that made them famous in the first place, it is refreshing to see someone who finds such immense success and joy from being who he always has been. He is not Robert Pattinson, ditching the Twilight ties to be Batman, or Blake Lively, eager to shy away from Gossip Girl anyway she can. He’s just Adam Sandler. The same Adam Sandler he’s always been. He’s happy to be himself and he’s happy to not be the greatest who ever did it, even though he could be. There’s a lot of respectability to be had for someone who never even considered his skill set as worthy of being the next Marlon Brando, but instead as worthy of making hundreds of millions of people happy.
He may do ten for him and one for us, but that is what makes the treats he creates so valuable along the way. I’m happy to keep growing old with him.
