Scroll through the slideshow or read the list below for our picks for the Top 10 Adam Sandler movies.
And be sure to let us know in the comments what you thought of our rankings and what your favorite Adam Sandler movies are.
10. Big Daddy
It’s not exactly a stretch for Sandler to play an unmotivated slob who refuses to face the realities of adult life. He tried this same ol’ shtick again in 1999’s Big Daddy, which stars Sandler as Sonny Koufax, a perpetual adolescent whose girlfriend gives him an ultimatum: Become responsible or kiss her goodbye. Who wouldn’t get their stuff together for Joey Lauren Adams? As it turns out, the young son of his roommate is left in Sonny’s care and the man finds new purpose in life… after copious amounts of bathroom humor, of course. Critics hated on the flick, but it went on to make $164 million at the box office.
9. Reign Over Me
Sandler returned to drama in 2007, starring opposite Don Cheadle in Mike Bender’s story of two old friends who are reunited in post-9/11 New York. Sandler plays a grief-stricken man who lost his wife and children in the attack. He’s completely shut down emotionally and regressed to a seemingly carefree life much like his college years, mostly playing PS2 and watching movies, while refusing to face his demons. The movie won generally positive reviews, and Sandler received further acclaim for his dramatic skills.
8. Funny People
Judd Apatow cast his old roommate Sandler as comedian-movie star George Simmons in this 2009 dramedy. George is forced to reevaluate his life when he learns that he has a potentially fatal blood disease. He reaches out to his estranged family and his now married ex-flame and returns to the world of stand-up comedy after years of making dumb movies. To help improve his act, George hires young, struggling comic Ira Wright (Seth Rogen) to write material for him. When he’s not berating and abusing him, the self-involved star reluctantly serves as a mentor to his new assistant.
7. 50 First Dates
This 2004 rom com reunited Sandler with his Wedding Singer costar Drew Barrymore. It tells the story of a marine biologist in Hawaii who, while living a lifestyle of one-night stands with tourists, unwittingly falls for a beautiful accident victim who wakes up every morning without her recent memory, forcing him to win her affections anew each day. It’s not exactly a great flick in the vein of Groundhog Day, but 50 First Dates is cuter and funnier than it’s often credited.
6. The Waterboy
The Waterboy may not have clicked with critics, but the 1998 comedy got plenty of laughs from moviegoers. Sandler’s turn as stuttering outcast-turned-football star Bobby Boucher is classic, and the movie also has the smoking hotness of The Craft actress Fairuza Balk going for it. Kathy Bates stars as Bobby’s over-the-top Cajun mom and Henry Winkler (The Fonz!) plays Coach Klein. If that’s not enough, The Waterboy features the first appearance of Rob Schneider’s “You can do it!” guy.
5. Billy Madison
Billy Madison was Adam Sandler’s big-screen breakthrough. The film, which Sandler wrote with frequent collaborator Tim Herlihy, was a perfect vehicle for his sophomoric humor — the story of a slacker who has to go back to school so he can take over his father’s company. Naturally, he’s got a hot teacher to help him out in the form of Mortal Kombat’s Bridgette Wilson. The film earned Sandler an MTV Movie Award for Best Comedic Performance and, more importantly, was a springboard to bigger and better things.
4. The Meyerowitz Stories (New and Selected)
Director Noah Baumbach succeeds in The Meyerowitz Stories (New and Selected) in fine fashion, delicately balancing serious issues with lighthearted moments – it is a movie that is equally adept at making the audience cry as it is with making them laugh. It is a feel good movie that it is impossible to leave without also having a sense of regret. With great characters and strong performances, including from Sandler as the son of Dustin Hoffman and brother of Ben Stiller’s characters, it is an utterly enjoyable, beautiful, film.
3. Punch-Drunk Love
Paul Thomas Anderson, director of Boogie Nights and Magnolia, had a hunch that Adam Sandler was an actor of far greater depth than he’d been given credit. And so he cast the Saturday Night Live alum in this 2002 drama, the story of a quiet, reclusive man who is transformed when a beautiful woman (Emily Watson) enters his life. The role was in some ways similar to Sandler’s socially awkward comic characters, but with a much darker and deeper tint. The performance earned Sandler a Golden Globe nomination.
2. The Wedding Singer
Yes, it’s an undeniable cheese-fest, but Sandler’s The Wedding Singer is the comic actor’s most widely appreciated film. The story follows jilted wedding singer Robbie Hart on a quest to save his crush, Julia (Drew Barrymore), from a marriage to her horrible fiancé, Glenn. And it’s all hilariously played out against the backdrop of mullets, skinny ties, and Culture Club tunes. The ’80s-set romantic comedy gave Sandler a chance to go for more than just the easy laughs and paved the way for him to enter the big time.
1. Happy Gilmore
Happy Gilmore stars Sandler as a hockey reject who takes up professional golf in order to save his grandma’s house. It’s a slapsticky comedy full of great gags, not the least of which are Happy’s golf course brawl with Price is Right host Bob Barker (“The price is wrong, bitch!”), and a hilarious Return of the Jedi parody finale. As is par for the course with Sandler flicks, some critics just didn’t get it, but Happy Gilmore is a clear favorite among the comic actor’s biggest fans.