The Best of Adam Sandler
- 14 hours ago
- 7 min read
Adam Sandler, who is currently starring in the George Clooney mess Jay Kelly, is one of those guys that everybody has an opinion about. For most people, he’s the loud, goofy, juvenile clown who made a fortune playing overgrown man-children who yell funny nonsense, punch people in the face, and fall down a lot.
For others (and I’d put myself in this camp) he’s a wildly talented performer who, yes, built an empire on dumb comedies, but who’s also capable of incredible depth, subtlety, and soul when he actually cares. The problem is, that only happens every few years.
He’s had one of the strangest careers in modern Hollywood, it's part genius, part embarrassment, part miracle, part migraine.
Sandler was born in Brooklyn in 1966, raised in Manchester, New Hampshire, and started performing stand-up at seventeen. He went to NYU’s Tisch School of the Arts, graduated in ’88, and pretty quickly found his way into the comedy world.
The first time I ever saw him was on Remote Control, that gloriously stupid MTV game show hosted by Ken Ober. I used to watch that all the time. Colin Quinn was on it. Denis Leary popped up. Kari Wührer was the eye candy.
And there was Adam Sandler, he was this weird kid doing goofy characters, cracking jokes, and you could tell right away: this guy’s brain works different. He was funny, awkward, unpredictable, and you couldn’t take your eyes off him.
From there he landed at Saturday Night Live in 1990. He started as a writer, then became a cast member, and before long, his songs (“The Chanukah Song,” “The Thanksgiving Song”), his characters (Cajun Man, Canteen Boy, Opera Man), and his complete lack of shame turned him into one of the most popular people on the show.
But those years were also controversial, because that early-’90s SNL run was a total boys’ club. Sandler, Chris Farley, David Spade, Rob Schneider... they dominated. It was frat house energy on live TV, and the female cast members (brilliant talents like Sarah Silverman and Janeane Garofalo) barely got screen time. It was chaos, but it was also funny as hell.
Then NBC fired him. And instead of disappearing, he turned it into the best thing that ever happened to him.
He went to Hollywood and made Billy Madison (1995), and everything changed. That movie was stupid, surreal, juvenile, and hysterical, and boy it made money.
Then came Happy Gilmore, The Wedding Singer, The Waterboy, Big Daddy… and suddenly, Sandler wasn’t just an SNL guy, he was a box office powerhouse.
His movies made hundreds of millions of dollars, even as critics absolutely savaged them. Didn’t matter. He had an audience that consisted of frat guys, teenagers, stoners, dads, anyone who wanted a laugh after work... and they showed up.
And then he started his own company (Happy Madison Productions) which basically turned into a lifelong excuse for him and his buddies (Spade, Schneider, Kevin James, Chris Rock) to hang out in Hawaii, make bad movies, and get paid obscene amounts of money.
The results? Little Nicky, The Ridiculous 6, Jack and Jill, Grown Ups 1 and 2, Hubie Halloween, movies that are lazy, dumb, and, let’s be honest, often painful to sit through. He made so much garbage that for a while people forgot he was ever funny, let alone good.
But here’s the thing: every few years, Adam Sandler does something extraordinary.
In 2002, he starred in Paul Thomas Anderson’s Punch-Drunk Love giving a performance so raw and unexpected it blew everyone away. Suddenly, this man-child who used to scream about shampoo and conditioner was heartbreaking.
It turned out that his signature man-baby energy (the rage, the sadness, the loneliness) could actually mean something in the hands of a real director. Since then, when Sandler works with talented filmmakers: people like the Safdie Brothers (Uncut Gems), Noah Baumbach (The Meyerowitz Stories), and Jeremiah Zagar (Hustle), he’s phenomenal.
When he’s lazy, he’s unbearable. When he’s focused, he’s a revelation.
That’s the duality of Adam Sandler. He’s capable of being one of the worst actors in the world on a Monday and one of the best actors alive by Friday. He’s the same guy who made Jack and Jill and Uncut Gems. He’s the guy who coasts through endless Netflix junk… and then turns around and gives a performance that knocks your head off.
And you know what? I respect that. Because even at his worst, he’s always himself. There’s something kind of punk rock about a guy who doesn’t care what the critics say, makes what he wants, and every once in a while surprises everyone with brilliance.
He’s been doing stand-up again, his Netflix specials have real heart, and he’s still turning out big movies. And somehow, 30 years later, the guy is more relevant than ever.
I’ve seen all of his stuff (the classics, the garbage, the hidden gems, the dramatic detours) and while I’ve hated plenty of his movies, I’ve also loved quite a few. And right now, with Jay Kelly out (his latest dramatic turn that’s actually getting raves) it’s the perfect time to celebrate the man’s career and count down the films where Sandler really shines.
These are my 10 favorite Adam Sandler movies and performances, ranked in order of my preference. Some are comedies, some are dramas, some are somewhere in between. But all of them show off the best of what he can do... when he’s not just cashing a check, but actually acting.
So here they are:
THE 10 BEST FILMS STARRING ADAM SANDLER (in order of preference):
This was the one that changed everything. Paul Thomas Anderson took the Sandler man-child (the anger, the loneliness, the bottled-up volcano of emotion) and gave it real depth. Suddenly, all the screaming and awkwardness meant something.
It was funny, heartbreaking, and hypnotic all at once. Sandler’s Barry Egan isn’t just his best performance, it’s one of the best performances of the 2000s. He should’ve been nominated for an Oscar. Every time I watch it, I still can’t believe the guy from Billy Madison pulled this off.
An anxiety attack of a movie. The Safdie Brothers gave Sandler his greatest dramatic role since Punch-Drunk Love, and he knocked it out of the park. Howard Ratner is chaos personified: sweaty, desperate, delusional, and absolutely magnetic. This movie doesn’t breathe.
It’s a nonstop panic attack set in the diamond district, and Sandler is riveting from start to finish. He should’ve won every award possible. Instead, he got robbed by the Academy... again.
This is the definitive Adam Sandler comedy. Loud, ridiculous, endlessly quotable, and somehow still sweet. Golf and hockey somehow merge into one of the most rewatchable comedies of the ‘90s.
Sandler’s rage fits are hilarious, the Bob Barker fight is legendary, and the supporting cast (especially Carl Weathers) is perfect. It’s stupid, yes, but it’s the right kind of stupid. It’s Sandler firing on all cylinders, and I still laugh like an idiot every time I watch it.
One of his most underrated movies, and one that proved he could play an actual grown-up. James L. Brooks directed this heartfelt dramedy, and Sandler gives a quietly powerful performance as a husband trying to hold his family together. It’s tender, awkward, and human.
No silly voices, no slapstick, it's just honest emotion. And the final scene with him and Téa Leoni is still gut-wrenching. People forget how good he is in this.
Noah Baumbach brought out another side of Sandler: the wounded, middle-aged, ordinary guy just trying to be seen. He plays Danny Meyerowitz, a divorced dad living in his father’s shadow, and he’s completely believable.
No shtick, no mugging, just a real, lived-in performance. Acting alongside Dustin Hoffman, Ben Stiller, and Elizabeth Marvel, he more than holds his own. Watching this after Jack and Jill is like seeing a different person.
The first great Sandler rom-com, and probably still the best. This movie is pure charm. It takes his goofiness and channels it into something sincere. His chemistry with Drew Barrymore is perfect, and that combination of ’80s nostalgia and genuine sweetness just works.
Plus, that “Grow Old With You” song still gets me every single time. It’s the movie that made him more than just a clown, it made him likable.
Another Netflix film, but one of the good ones, it is a heartfelt, well-made sports drama. Sandler plays a down-on-his-luck basketball scout trying to prove himself, and it’s honestly one of his most grounded performances.
You can tell he loves basketball (it’s in his DNA) and that authenticity shines through. The movie’s got heart, great cameos, and a ton of soul. It’s his best work in years, and proof that when he wants to, he can still deliver something special.
This is where it all started. The stupid voices, the absurd premise, the juvenile jokes... and somehow, it’s still hilarious.
It’s pure ‘90s nonsense, but it’s also the blueprint for everything that came after. Watching it now feels like nostalgia in its purest form. Sandler was young, weird, fearless, and clearly having a blast. “O’Doyle rules!” will always make me laugh.
A total time capsule of ‘90s comedy, and one of the few times Sandler was part of a great ensemble. Alongside Brendan Fraser and Steve Buscemi, he plays one of three wannabe rockers who take over a radio station to get their song played.
It’s ridiculous, yes, but also surprisingly sharp about the music business. Sandler’s not the lead, but his energy is infectious, and it’s one of the first times he proved he could steal scenes without screaming.
A deep cut, a brilliant one, and a weird one. Bobcat Goldthwait’s dark, twisted cult comedy about depressed, alcoholic clowns is truly one of a kind. Sandler has a small role, but it’s one of his earliest film appearances and shows exactly why people noticed him.
He’s strange, funny, and magnetic even in the background. The movie itself is bizarre but fascinating, it's like a demented cousin of The King of Comedy. You can feel the seeds of the Sandler persona starting to form here.
There it is... the ten best films starring Adam Sandler, ranked in order of my preference. He’s had one of the most uneven careers in Hollywood, capable of brilliance one moment and utter disaster the next... but when he’s good, he’s really good.
These are the performances that remind you why he’s lasted this long, why he keeps surprising people, and why, when the stars align, Adam Sandler can still knock it out of the park.
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