What is there left to say about Adam Sandler? The Sand-Man has been a fixture of pop culture for well over 20 years, having worked first on Saturday Night Live and then broken out in a series of farcical, wonderful comedies in the years after his departure. He’s one of the biggest comedy stars on the planet, and he’s been part of some of the best comedy movies. He’s also made plenty of movies that nobody should be forced to watch twice.
For every movie that has immediately been relegated to the trash bin of history, though, Sandler has also made an indelible comedy or a surprising turn into drama. While he could have emerged looking a little bit like a one-trick pony who relies on funny voices for cheap laughs, Sandler turned out to be far more complicated than that. He is a genuinely great actor whenever he wants to be. The rest of the time, he’s content to make silly movies with his best friends.
The Waterboy (1998)
90m
Genre
Comedy
Stars
Adam Sandler, Kathy Bates, Fairuza Balk
Directed by
Frank Coraci
“Now that’s what I call high-quality H20.” The first of his legendary run of great comedies, The Waterboy is all-out ridiculousness and is filled with the kind of quotable lines that are still repeated today. Bobby Boucher (Sandler) is a waterboy for his local college football team, but he gets a chance to play for another team when his anger is accidentally unleashed and Bobby puts an enormous player on his back. Sandler adopts his trademark childlike voice in this role, which only adds to the overall hilarity of this already pretty funny movie.
Funny People (2009)
146m
Genre
Comedy, Drama
Stars
Adam Sandler, Seth Rogen, Leslie Mann
Directed by
Judd Apatow
A nostalgic throwback to Sandler’s early standup comedy career, Funny People is a well-written comedy with substantial emotional depth. The film follows a recently diagnosed, terminally ill standup comedy legend named George Simmons (Sandler) who feels like life has passed him by. He decides to take on some new blood (Seth Rogen) to open his comedy tour, and ultimately becomes friends with this up-and-coming comedian. Sandler has rarely been more nakedly emotional than he is here, and he turns in one of his best performances.
The Wedding Singer (1998)
95m
Genre
Romance, Comedy
Stars
Adam Sandler, Drew Barrymore, Christine Taylor
Directed by
Frank Coraci
One of the better romantic comedies of our generation, The Wedding Singer is a genuine, sweet story about a boy who meets and falls for a girl, but realizes he can’t have her. When a low-income wedding singer is left at the altar by what he thinks is the love of his life, he must put the pieces of his heart back together. Luckily, he meets the charming Julia Sullivan (Drew Barrymore) who makes the process much easier. Full of cameos from many of Sandler’s friends, this is a feel-good Valentine’s Day movie that will have your partner asking, “When are you going to do that for me?”
Reign Over Me (2007)
124m
Genre
Drama
Stars
Adam Sandler, Don Cheadle, Jada Pinkett Smith
Directed by
Mike Binder
In one of his most impressive dramatic roles, Reign Over Me was yet another opportunity for the comedian to show off his range. After losing his entire family, Charlie Fineman (Sandler) runs into his old college roommate, Alan Johnson (Don Cheadle), and they rebuild a friendship that could very well save Charlie’s life. This role is a far cry from anything viewers expected from Sandler in the best possible way.
Big Daddy (1999)
93m
Genre
Comedy, Drama
Stars
Adam Sandler, Joey Lauren Adams, Jon Stewart
Directed by
Dennis Dugan
“Scuba Steve!” Another film that blends comedy and sentimentality, Big Daddy is a good Father’s Day movie if you’re looking for a laugh. After his girlfriend breaks up with him for another man, Sunny (Sandler) decides to adopt a kid to show his maturity, and it goes about as well as you might expect. With some endearing moments of innocence from the young Julian (Cole Sprouse), we see what could happen when a child is adopted by an aimless man-child.
Uncut Gems (2019)
136m
Genre
Drama, Crime, Thriller
Stars
Adam Sandler, Julia Fox, Lakeith Stanfield
Directed by
Josh Safdie, Benny Safdie
A Safdie brothers treasure, Uncut Gems is an emotional and gritty thriller starring our unlikely comedian, who shines in one of the most anxiety-inducing movies you’re ever likely to see. With a legendary score designed to keep the audience’s rapt attention, we follow a crafty, talkative jeweler through the streets of New York as he attempts to win big at the risk of losing it all. Sandler’s performance in this film is the cherry on top of an overall well-made thriller, proving that he is nowhere near done exploring what he’s capable of.
Billy Madison (1995)
90m
Genre
Comedy
Stars
Adam Sandler, Bradley Whitford, Josh Mostel
Directed by
Tamra Davis
“O’Doyle rules!” In what is probably the least intelligent comedy on this list, Billy Madison nonetheless remains a staple in the Adam Sandler comedy must-sees. When his wealthy father decides to pass on his empire of hotels, immature, uneducated, and alcoholic Billy Madison (Sandler) makes a deal to re-take grades 1-12 in order to inherit the business. While it seems Sandler’s may really enjoy ruining the innocence of kids on screen, this movie is also notable in that it was the big-screen birth of one of Sandler’s signature voices — not counting his time on Saturday Night Live.
Punch-Drunk Love (2002)
96m
Genre
Comedy, Drama, Romance
Stars
Adam Sandler, Emily Watson, Philip Seymour Hoffman
Directed by
Paul Thomas Anderson
A unique tale of love and loneliness, Punch-Drunk Love was the moment Sandler showed everyone what he was capable of. When Barry (Sandler) contacts a phone-sex line to help with his loneliness, things turn in the worst way for the business he owns, his personal finances, and the love that is slowly forming with an unexpected partner. Endearing, romantic, and jarringly intense at times, this is definitely one of Sandler’s most memorable and watchable movies of the 2000s.
50 First Dates (2004)
99m
Genre
Comedy, Drama, Romance
Stars
Adam Sandler, Drew Barrymore, Rob Schneider
Directed by
Peter Segal
Another Adam Sandler rom-com also featuring Drew Barrymore, 50 First Dates is a comical dramedy that honestly gets pretty sad at times. Henry Roth (Sandler) is a ladies’ man who can’t commit. When he finally meets the girl of his dreams, she turns out to have short-term memory loss, resetting the clock on their relationship every day when she goes to sleep. 50 First Dates earned its spot on this list because, while it’s occasionally a bit sentimental, it’s a genuinely winning romance that gets at what it means to truly love someone.
Happy Gilmore (1996)
92m
Genre
Comedy
Stars
Adam Sandler, Christopher McDonald, Julie Bowen
Directed by
Dennis Dugan
“The price is wrong, bitch.” Most likely responsible for lots of people being banned from golf courses, Happy Gilmore follows Happy (Sandler), a wannabe hockey player. After accidentally finding out his talents truly shine on the golf course, he takes up the game to raise enough money so that his grandmother can keep her house. Happy Gilmore may be Sandler’s best comedy movie ever, and it gained that reputation because at no point does it pretend to be serious. It’s also, strangely enough, one of the best golf movies ever.
The Meyerowitz Stories (New and Selected) (2017)
112m
Genre
Comedy, Drama
Stars
Adam Sandler, Ben Stiller, Dustin Hoffman
Directed by
Noah Baumbach
Another dramatic turn, The Meyerowitz Stories follows three adult siblings as they attempt to navigate their parents, their relationships with one another, and life more generally. Sandler plays one of these siblings, and he’s genuinely great as a man who seems to just be barely holding back his anger at every possible moment. This is another naturalistic performance from Sandler, and one that reminded audiences that he doesn’t have to do a silly voice in order to deliver a totally winning performance.
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