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Adam Sandler's 8 Best Movies

Adam Sandler's 8 Best Movies


Few things are as magical as enjoying a movie on a big screen, in a dark theatre surrounded by fellow film-lovers. There's a delightful anticipation as the lights dim and everyone gets ready to experience something entertaining and exciting, and perhaps even discover a new favorite movie.

We're not quite ready to get back to packed houses just yet, but to celebrate the reopening of theatres, we’re screening some of your all-time favorite movies—including the rom-com hit 50 FIRST DATES. It was difficult to pick just one movie from all of Adam Sandler's films, which is why we’re taking a look back at the best roles from the iconic actor’s remarkable career.

Billy Madison

Adam Sandler's Best Movies: Billy Madison

[Image Credit: Universal Pictures]

In 1995, four years after he started his memorable run on “Saturday Night Live,” and after appearing in a couple of films as a supporting player, Adam Sandler starred in the first of many hit films. The crooning, crazed comedian stars as Billy Madison, the slacker scion of a wealthy hotel tycoon. Billy’s dad doesn’t trust his immature, spoiled son to take over the business, so he comes up with a challenge. Billy only got through elementary and high school because his dad paid off all the administrators, so pop gives Billy 24 weeks to complete and pass all 12 grades. BILLY MADISON established Sandler's movie image as a lovable under-achiever who defies expectations to become the man he needs to be. With Sandler’s trademark silly humor and appearances from frequent collaborators like Steve Buscemi and the late Chris Farley, BILLY MADISON isn’t just Sandler’s first big hit comedy—it’s one of his very best.

Happy Gilmore

Adam Sandler's Best Movies: Happy Gilmore

[Image Credit: Universal Pictures]

Just a year after BILLY MADISON, Sandler followed up with HAPPY GILMORE. The two films are similar in structure, as both center on a likable but volatile underachiever, but Sandler offers a different performance in the latter movie. While Billy Madison is a goofy man-child with the sensibilities of a 12-year-old boy, "Happy" Gilmore is an insecure aspiring hockey player who can’t seem to catch a break because to put it plainly, he’s not very good on the ice. HAPPY GILMORE allows Sandler to showcase another of his signature approaches to comedy as he creates a character whose weakness ultimately becomes his strength. In the process, he gets to save his nice grandma from an evil Ben Stiller, too.

The Wedding Singer

Adam Sandler's Best Movies: The Wedding Singer

[Image Credit: New Line Cinema]

There would be no 50 FIRST DATES without THE WEDDING SINGER, which was the first of three rom-coms starring Adam Sandler and Drew Barrymore. Sandler plays the anger-prone Robbie Hart, a wedding singer who loves romance and the idea of getting married. When his fiance Linda leaves him at the altar, it sends Robbie into a spiral. That is until he meets Julia (Barrymore) a lovely waitress who is unfortunately engaged to a total jerk. As Robbie helps his new friend plan her wedding, the two begin to fall for one another, leading to one of the most delightful and sweet rom-com endings of all time. Sandler’s musical talents were well-known among his fans, but THE WEDDING SINGER introduced them—along with the actor's softer side—to a wider audience, and proved that he could be a genuine rom-com love interest.

Big Daddy

Adam Sandler's Best Movies: Big Daddy

[Image Credit: Sony Pictures]

The set-up is familiar for an Adam Sandler comedy: Sonny Koufax is a very likable 32-year-old guy, but he’s got a lot of growing up to do. After Sonny’s fiance leaves him for an older (much, much older) man, a cute five-year-old kid (played by famous acting twins Dylan and Cole Sprouse!) shows up at his doorstep. Turns out the kid belongs to Sonny’s best friend, who just left the country for work. In a misguided attempt to prove his maturity to his ex, Sonny takes the kid in as his own. In classic feel-good comedy fashion, despite being the parental figure, Sonny ends up learning a lot from his new pint-sized charge.

Punch-Drunk Love

Adam Sandler's Best Movies: Punch-Drunk Love

[Image Credit: Sony Pictures]

By 2002, Sandler had established a very specific brand of comedy, often starring in movies opposite the same actors (many of whom are his longtime friends) and telling stories about the same kinds of characters. Sandler broke his own mold with PUNCH-DRUNK LOVE, a dark romantic drama from BOOGIE NIGHTS director Paul Thomas Anderson. The filmmaker turned the familiar Sandler character inside-out with a story about a lonely and introverted bathroom supply business owner with anger issues. The guy comes out of his shell when he meets his sister’s co-worker, played by an equally shy and eccentric Emily Watson. Their love is strange and beautiful but is threatened when Sandler’s vulnerable character falls prey to an extortionist, played by the late Philip Seymour Hoffman.

50 First Dates

Adam Sandler's Best Movies: 50 First Dates

[Image Credit: Sony Pictures]

We can’t revisit Sandler’s best roles without including the film featured in our Comeback Classics series: 50 FIRST DATES. The funnyman reunited with Drew Barrymore for this oddball rom-com that once again incorporates Sandler’s musical talents for a surprisingly sweet and hilarious story. Sandler plays Henry, a veterinarian, and womanizer who spends his free time hooking up with female tourists in Hawaii before making up elaborate excuses to ditch them. Then Henry meets Lucy (Barrymore), a charming young woman with a very specific form of amnesia that causes her to forget each day’s events when she goes to sleep at night. Henry falls for Lucy and becomes determined to make their relationship work, proving his commitment not only to her father and brother (a memorable turn from LORD OF THE RINGS star Sean Astin), but to himself. Over the course of many weeks, Henry takes Lucy on 50 "first" dates, resulting in a romance that is both comical and quite moving.

Funny People

Adam Sandler's Best Movies: Funny People

[Image Credit: Universal Pictures]

Judd Apatow’s FUNNY PEOPLE is similar to PUNCH-DRUNK LOVE in that it takes advantage of our familiarity with Sandler to create an effective story with a slightly more dramatic performance than we're used to seeing from the actor. In FUNNY PEOPLE, Sandler plays George Simmons, a comedian who is well-known for starring in comedy movies that are all fairly similar—basically a fictional version of Sandler himself. FUNNY PEOPLE uses real-life criticism levied at Sandler and his movies as inspiration for a story about a comedian who, diagnosed with a fatal illness, takes on a protege (Seth Rogen) and rediscovers what he loves about life, his work, and his family.

Uncut Gems

Adam Sandler's Best Movies: Uncut Gems

[Image Credit: A24]

This riveting thriller from 2019 features Sandler in his most dramatic and provocative role yet; it's unlike anything he had done before. UNCUT GEMS stars Sandler as Howard, a charismatic jeweler who is increasingly overwhelmed by mounting life stresses. Howard’s gambling addiction leads to a mountain of debt with increasingly dangerous repercussions; his estranged wife and children are (understandably) demanding of his time; he’s insecure about his relationship with a younger mistress; and a famous basketball player (real-life NBA star Kevin Garnett, playing himself) has taken off with the extremely valuable gem that Howard believes will solve all his problems. UNCUT GEMS is one of the most intense thrillers ever made and features one of the best and most surprising performances of Sandler’s career.

Check out the rest of our Comeback Classics lineup!

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