Adam Sandler’s 12 Best Movies for Grownups

Watch hilarious farces, heartwarming rom-coms and gripping tragedies starring the biggest matinee idol ever spawned by ‘Saturday Night Live’

Chris Nashawaty,

AARP

Comments

Published July 25, 2025

adam sandler swinging a golf club in 'happy gilmore 2'

Adam Sandler returns to the titular role in “Happy Gilmore 2” (2025).

BFA/Netflix/Alamy Stock Photo

Of all the comedians who graduated from Saturday Night Live to even greater success in movies, none can match the box-office might — and longevity — of Adam Sandler, 58. Back in the early ’90s, you would’ve been forgiven for betting against him. But his post-SNL career has been a charmed string of hits. On July 25, Sandler’s latest film, Happy Gilmore 2, the long-awaited sequel to the beloved 1996 golf comedy, arrives on Netflix. So it’s a good time to celebrate these, his 12 greatest movies.

Billy Madison (1995)

After five indelible seasons, Sandler left the cozy confines of SNL and headed west. His first comedy out of the gate was this goofy tale about the dim son of a filthy-rich mogul (Darren McGavin) who has to repeat his K-12 school years to prove he’s not an idiot and that he’s ready to be an heir. A deliriously silly guilty pleasure.

Watch it

Don't miss this: 7 Things You Didn’t Know About Adam Sandler (video)

Happy Gilmore (1996)

Was Billy Madison a fluke? Sandler’s immediate follow-up proved he was more than a one-hit wonder. It’s easy to see why this remains a fan favorite. Showing early glimmers of the rage simmering beneath his clownish exterior, Sandler plays Happy Gilmore, a short-fused hockey player who channels his volcanic temper into big-hitting golf stardom. If you ever wanted to see The Price Is Right host Bob Barker clock someone, you’re in luck. A wonderfully ridiculous movie you can’t watch too many times.

Watch it

The Wedding Singer (1998)

A breakout rom-com for Sandler, The Wedding Singer is also a hilarious time capsule from the New Wave ’80s. The actor gets to show a more sentimental side here, opposite an adorable Drew Barrymore, 50. This MTV-era meet-cute was much better than most critics were expecting. It ended up painting the comedian in an entirely new light and paving the way for two more rom-com collaborations with Barrymore.

Watch it

The Waterboy (1998)

Bobby Boucher, a waterboy picked on and made fun of for 31 years until he erupts, is yet another one of Sandler’s raging goofballs. But what elevates this seemingly disposable football comedy is its heart and its much-better-than-it-needs-to-be supporting cast, particularly Henry Winkler, 79, as Bobby’s coach, and Kathy Bates, 77, as Bobby’s mama. It’s basically Billy Madison on the bayou, but the scenes between Sandler and Bates are worth the price of admission.

Watch it

Big Daddy (1999)

You might not think of turning to an Adam Sandler movie for parenting tips, but this bigger-budgeted effort from the clown has a surprisingly poignant take on fatherhood. He plays a thirtysomething layabout who tries to win back his ex by adopting a child (you know, to show he’s mature and responsible). Needless to say, the plan doesn’t work, but there’s humor and a surprising amount of heart along the way.

Watch it

Punch-Drunk Love (2002)

Sandler was always popular with everyday moviegoers, but it wasn’t until this disarmingly dark comedy from art house auteur Paul Thomas Anderson, 55, that critics gave him their (reluctant) stamp of approval. It’s a performance that contains multitudes. Sandler plays a lonely, bottled-up, invisible man, henpecked by seven terrifically pushy sisters, who tries to open himself up when he falls in love with a mystery woman (Emily Watson, 58). Anyone who doubted that Sandler was a real actor going into this movie wasn’t doubting it when they came out.

Watch it

50 First Dates (2004)

Sandler’s second date with Drew Barrymore rekindles their spark from The Wedding Singer and leads to another genuinely delightful rom-com with some DNA from Groundhog Day. Sandler plays a commitment-phobe who finally meets Mrs. Right, only to discover that she suffers from short-term memory loss. As a result, he has to win her over again and again and again. 50 First Dates hits the rainy-afternoon bull’s-eye.

Watch it

Funny People (2009)

Directed by Judd Apatow, 57, this sharp, sober comedy pauses between punch lines to grapple with some real emotional complexities. Sandler plays a stand-up comic diagnosed with leukemia. With the end possibly in sight, he tries to make amends with his ex (Leslie Mann, 53) and takes a young comic under his wing (Seth Rogen). Arguably Sandler’s first mature role.

Watch it

Uncut Gems (2019)

Hands down, Sandler’s most exciting — and tragic — performance. In this high-tension New York thriller, he plays a diamond dealer with a serious gambling problem. With each long-shot bet, he gets deeper and deeper into debt. Eventually, he’s just trying to stay one step ahead of the bruised-knuckle types coming to collect. If you’re in the mood for leisurely comfort viewing, this is not the movie for you. Uncut Gems is a tense underworld workout.

Watch it

Murder Mystery (2019)

Jennifer Aniston, 56, makes a bid to become the new Barrymore in this dizzy rom-com whodunit. Aniston and Sandler play a long-married couple on holiday in Europe who get invited onto a billionaire’s yacht, only to end up becoming Nick and Nora–style sleuths after he’s murdered. This is a fun and frantic sleeper with lots of Lifestyles of the Rich and Famous eye candy.

Watch it

Hustle (2022)

In another terrific (and underseen) Sandler performance, he plays Stanley Sugerman, a down-and-out NBA basketball scout who tries to stay in the game by risking everything on a talented street ballplayer (Juancho Hernangómez) he discovers in Spain. Think of this as Sandler’s Jerry Maguire. Queen Latifah, 55, is beyond fantastic as Sandler’s beautifully supportive wife.

Watch it

You Are So Not Invited to My Bat Mitzvah (2023)

Proving apples don’t fall far from the tree, this teenage rite-of-passage comedy stars Sandler as well as his three real-life daughters: Jackie, Sunny, and Sadie. Sandler is as funny as you’d expect as a put-upon dad suffering through the pricey planning of his daughter’s big day in the eyes of God and her classmates. However, the real revelation here is the next generation of Sandlers. They’re really good. So’s the movie.

Watch it

%{postComment}%

Chris Nashawaty, former film critic for Entertainment Weekly, is the author of Caddyshack: The Making of a Hollywood Cinderella Story and a contributor to Esquire, Vanity Fair, The New York Times and The Wall Street Journal.