A name that is and has been synonymous with goofy comedy movies for decades, Adam Sandler has brought a style of his own to a generation that either loves or hates him. Either is acceptable, as out of the close to 50 movies he’s starred in, it’s fair to say that maybe half of them are worth watching. That is, unless, you’re a die-hard Sandler fan. But you have to admit that if you had the chance to fly all your closest friends to some island destination and make a few million bucks while you do it, you probably wouldn’t care too much about the critics.
People who grew up with Sandler have been through one hell of a ride. From endlessly quotable comedy classics such as The Waterboy, Billy Madison, and Happy Gilmore to his later and surprisingly successful dramas, Sandler forever inhabits a place in the hearts of millennials. Besides his wide array of movies, Sandler also has some incredibly memorable skits from his time on Saturday Night Live. Because of his honorable comedic history, I’m sure we can agree that judging him from a handful of movies like Jack & Jill or The Ridiculous 6 wouldn’t be fair. This is why we are here to praise Sandler for his achievements on screen, not his failures — though the aforementioned are abominable.
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 comedic greatest hits, The Waterboy is all-out ridiculousness with the forever quotable lines that are still repeated to this day. 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 lays out a player. The childish and signature voice he decided to adopt is a big part of the hilarity, turning his hard-hitting defensive lineman into the man-child he is.
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 that is worth the watch. For recently diagnosed, terminally ill standup comedian George Simmons (Sandler), it feels like life has passed him by, but this doesn’t stop him from taking on some new blood (Seth Rogen) to open his comedy tour. As one of his overall better films, it’s a great bonus to see other standup comedians make appearances and stretch their legs on the big screen.
The Wedding Singer (1998)
95m
Genre
Romance, Comedy
Stars
Adam Sandler, Drew Barrymore, Christine Taylor
Directed by
Frank Coraci
One of the better romantic comedy movies of our generation, The Wedding Singer is a genuine and sweet story of boy meets girl but 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 the classic Sandler movie cameos and silly songs, 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 arguably Sandler’s first real chance to show what he can do. 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 this doesn’t go well. 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.
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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 a new genre of torrential anxiety. 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, or else lose it all. Sandler’s performance in this film is the cherry on top of the overall well-made thriller, proving that he is nowhere near done expanding in the film industry.
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 movie 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 definitely got a thing for ruining the innocence of children on screen, this movie is also notable in that it was the big-screen birth of the Adam Sandler signature voice — 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
In an extremely unique tale of love and loneliness, Punch-Drunk Love is a little strange to experience but still holds together as a highly entertaining and funny movie. 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 but has some moments of wonderful devotion and love to aspire to — even though it’s just a movie. Henry Roth (Sandler) is portrayed as a ladies’ man who can’t commit — which, in all honesty, falls by the wayside pretty quickly in the plot. When he finally meets the girl of his dreams, she turns out to have short-term memory loss, resetting the clock every day when she goes to sleep. Besides being a bit corny and a little lazy in its writing, the moments of love and adoration are something to behold, especially if shared with your loved one and the tears can be contagious.
Read More: Best Romantic Comedies of All Time
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), who is 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. As maybe his best comedy movie ever, this movie gained that reputation because at no point does it pretend to be serious but instead stays true to its nature and ends up being one of the best golf movies ever.
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