There’s rom-coms, buddy-comedies, action-comedies, and then there’s Adam Sandler comedies. A genre of its own. Very few actors manage to become a one man brand, but Sandler has built an empire out of weird voices, heartwarming chaos, and eternal man-child charm. From family-friendly hits like Big Daddy to raunchy laugh-riots like Grown Ups, Sandler’s got range, even if it is wrapped in cargo shorts and dad jokes. And considering that the man never really takes a break, he just films holiday movies with his besties in tropical locations, the Sandman has been regularly pumping out gold since the 90s, making sure there’s always something ridiculous and oddly comforting to watch.
Here’s a rundown of 10 of his funniest, most iconic, and downright different films—because yes, the Sandman has proved that he can do more than just scream at your face in a silly voice (though he’s great at that too):
10. Just Go With It (2011)
A man lies to impress a woman, lies again to cover the first lie. Then invites his assistant, her kids, and his crazy cousin on a vacation to somehow cover it all up. At face value, Just Go With It might seem like a mid-tier rom-com with a predictable storyline, but with Sandler and Jennifer Aniston at the centre, it turns into something endlessly rewatchable. And the Hawaiian backdrop certainly doesn’t hurt.
Aniston is effortlessly funny and grounded, Sandler is surprisingly charming, and together they turn this lie-filled plot into a fun, low-stakes, feel-good romantic-comedy perfect for an easy night in with friends or a casual date. It’s all mostly harmless fun, aside from a few eyebrow raising jokes that aren’t exactly kid-friendly.
9. Billy Madison (1995)
For many, Billy Madison is the gateway drug into the world of Adam Sandler. Adam Sandler plays a literal manchild who is forced to repeat school from kindergarten to high-school in order to inherit his father’s fortune. Sandler of course leans into the madness, delivering a glorious mix of juvenile humour, nonsense plotlines, and endlessly quotable one-liners (T-T-T Today, Junior.)
It’s dumb in the best way, and if you grew up on loud, slapstick, 90s comedies, Billy Madison is a nostalgic fever dream. If not, it might take you a minute to get used to the sheer level of absurdity in the film, and dated jokes, but it’s still a solid choice if you’re in the mood for a mindless, no-logic needed PG-13 comedy.
8. Big Daddy (1999)
Who knew that the chaos of watching an emotionally stunted man-child take care of a five-year-old would give us one of Sandler's most memorable roles? Big Daddy is what happens when you give a man-child full custody of an actual child, expecting Happy Meals for breakfast, peeing on a building, spontaneous Hooters call outs.
But somewhere in the middle of all the laughs, you’ll find yourself completely invested as it turns into a courtroom battle. With the adorable Sprouse twins tag-teaming the role of Julian, Big Daddy, is a no-frills comedy that pulls at your heartstrings just as much as it makes you laugh. If you enjoy a good messy-man-turned-softie story, with plenty of gross out gags, loud slapstick, and some emotional payoff, Big Daddy is the way to go for movie night.
7. Happy Gilmore (1996)
What do you get when you cross a failed hockey player with anger issues and a golf course? Three words: Classic Sandler Ragefest. Sandler plays a short-fused underdog with a killer golf shot in this outrageous sports parody that takes the elite game of golf and turns it entirely upside down. Coming in just a year after Billy Madison, Happy Gilmore was a part of the Early Sandler formula, a mix of loud, absurd, immature, but oddly endearing characters.
Even if you’re not into golf, with its unforgettable zingers, surprising cameos, and perfect balance of heart and humour, Happy Gilmore promises an entertaining watch, especially if you grew up on 90s humour, love a good underdog story, or just want to watch Sandler punch someone on a golf course. Plus, with Happy Gilmore 2 now streaming on Netflix, there’s never been a better time to revisit the classic.
6. Grown Ups (2010)
The ultimate Sandler vacation movie, Grown Ups stars Adam Sandler in a comedy sandbox alongside Kevin James, Chris Rock, David Spade, and Rob Schneider, four of his longtime friends. Grown Ups is less about the plot and more about the vibes. Five childhood best friends reunite to spend a weekend together at a lake house after their beloved high school basketball coach passes away.
Think lots of dad jokes, family drama, and a weekend full of grown men acting like kids. It’s essentially a home video of Adam Sandler hanging out with his friends. There’s a lot of fart jokes, waterpark misadventures, and chaotic group energy. This one’s not made to win any awards or impress critics, but it is the go to feel-good flick for when you’re with your best friends, and just want to turn off your brain and laugh. And if one weekend of dad jokes and lake house drama isn’t enough, there’s always Grown Up 2 to double down on the mayhem.
5. The Wedding Singer (1998)
Robbie Hart, a hopeless romantic and professional wedding singer spirals into a heartbreak fuelled funk after being jilted at the altar. That is, until he meets Julia—a sweet, kind, and quirky waitress with a wedding of her own on the horizon, giving him something (and someone) worth singing about again.
A certified fan favourite, The Wedding Singer is a welcome break from Sandler’s usual man-child chaos. Set in the neon-soaked, synth-heavy world of 1980s New Jersey, it’s equal parts nostalgic, sweet, and hilarious. It also marks the beginning of Sandler and Drew Barrymore’s on-screen magic, kicking off one of rom-com’s most beloved duos. If you love feel-good stories with a touch of retro flair, and a killer soundtrack, this one’s for you.
4. Hustle (2022)
We’re in serious Sandler territory now. Adam Sandler plays Stanley Sugerman, a down on his luck NBA scout who bets everything on an undiscovered streetball prodigy, by bringing him to train with him in the US without his team’s approval, betting that both of them deserve to be in the big leagues.
Free from his usual screaming and fart jokes, Hustle shines as a true underdog story packed with emotion, gut, and appearances from real NBA players and legends like Anthony Edwards, Kenny Smith, Trae Young, and Julius Erving. Sandler delivers one of the best performances of his career as a coach who’s equally as worn down as he is hopeful. This movie is a total slam dunk for anyone who loves basketball or a good underdog movie.
3. 50 First Dates (2004)
Romance, tragedy, and goofy comedy all rolled into one, 50 First Dates walks a tightrope between heartwarming and heartbreaking. Set in the sun-soaked backdrop of Hawaii, the movie follows Henry, a marine vet who sets out on an endless loop of first dates after falling hopelessly in love with Lucy, a girl suffering from short-term memory loss. What follows is a daily do-over filled with penguins, ukuleles, and unexpected tears.
Quirky, offbeat, and slightly crude, it’s got everything you’d expect from a classic early 2000s rom-com, and more. Sandler and Barrymore share effortless chemistry, building on their magic from The Wedding Singer. If you’re in the mood for that early 2000s rom-com magic, complete with a tropical setting, a feel-good soundtrack, and a love story that doesn’t quit, 50 First Dates checks all your boxes.
2. Punch Drunk Love (2002)
Paul Thomas Anderson is a genius when it comes to matching well established actors with uncharacteristic roles that come as a welcome surprise to their fans. And he proved this when he cast Sandler as Barry, a mentally troubled, lonely guy in love in Punch Drunk Love.
A total departure from his usual man-child comedies, Sandler plays the role of a lonely, mentally unstable man courting the sweet and shy Lena to the tee, bringing his signature rage fits, with a never before seen sense of vulnerability and emotional restraint that gives the film its offbeat charm, artistic flair, and raw emotional depth. Punch Drunk Love proved early on that Sandler isn’t just a funny guy, and is a must watch for both Sandler fans and lovers of unconventional romantic dramas.
1. Uncut Gems (2019)
The chaotic and artful world of A24 collides with Adam Sandler to deliver a career-defining performance that should have bagged him an Oscar. Sandler plays a fast-talking New York jeweller and gambling addict who’s constantly chasing the next big win. With dizzying camera work, a relentless pace that doesn’t leave any room to breathe, and Sandler’s raw, desperate, and magnetic performance as a jeweller and gambling addict juggling debt collectors, furious clients, and a crumbling personal life, Uncut Gems, is pure cinematic stress but in the best way possible.
That said, it’s unlike anything he’s done before, and it’s definitely not for everyone. If you’re in the mood for fast-talking hustlers, high-stakes drama, and relentless pacing, Uncut Gems is your kind of film. But if you’re after something more lighthearted and easy going, Sandler’s other comedies might be a better fit.
