Adam Sandler and wife, Jackie, arriving to “Jack and Jill” Premiere in 2011

Adam Sandler and wife, Jackie, arriving to "Jack and Jill" Premiere in 2011 (Photo by DFree on Shutterstock)

Adam Sandler, the master of slapstick humor and witty one-liners, has the ability to turn even the most mundane situations into uproarious comedy gold. Whether he’s playing a bumbling waterboy, a zany wedding singer, or an overgrown man-child in a million-dollar suit, Sandler’s brand of humor is a delightful escape from the ordinary comedy films. The best Adam Sandler movies never fail to make you laugh and usually boast a star-studded cast.

One of the reasons Sandler’s movies are so side-splittingly funny is his knack for taking relatable, everyday scenarios and cranking up the absurdity. The best Adam Sandler movies have characters that are relatable in their quirks and flaws, which makes the humor all the more endearing. It’s this blend of the familiar and the outlandish that makes Sandler’s movies so endlessly entertaining.

Classics like “Happy Gilmore” and “Billy Madison” showcase Sandler’s signature humor and irreverent style, earning a special place in fans’ hearts. Meanwhile, more recent works like “Uncut Gems” have demonstrated Sandler’s versatility as an actor, earning critical acclaim and showcasing his ability to tackle dramatic roles with finesse.

From “The Wedding Singer” to “Uncut Gems,” StudyFinds has crafted the ultimate list of the best Adam Sandler movies, ranked by the experts. So, whether you’re in the mood for a dose of nostalgia or just a good, hearty laugh, pop in an Adam Sandler movie and get ready for a wild, wacky, and wonderfully funny ride. Which is your favorite? Leave a comment to let us know!

Adam Sandler's Hollywood Walk of Fame star
Adam Sandler’s Hollywood Walk of Fame star (Photo by Hayk_Shalunts on Shutterstock)

The List: Best Adam Sandler Movies, According to Experts

 

1. “The Wedding Singer” (1998)

Adam Sandler shines bright like a diamond in the one film that was highly rated on every single movie buff’s favorite list of Adam Sandler films. “For all the serious acting Sandler has done in his career, this is his best of it,” writes Esquire. “Surprisingly, this film, lovingly set in the ’80s, has aged remarkably well of Sandler’s Golden Years of the late ’90s. He and Barrymore—their first of many lesser films together together—have real chemistry, making this the best true rom-com of his career.”

"The Wedding Singer" (1998)
“The Wedding Singer” (1998)

“Sandler tends to make raunchy, almost nihilistic comedies. The Wedding Singer dropped him in the romantic comedy world. Yes, a lot of the humor is derived from ‘80s references, but a lot of that is fun. Also, the romantic stuff works, and Sandler deserves some of the credit for that,” adds Yardbarker.

Some movie critics applaud Sandler for his ability to make us fall in love with him. “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,” says The Manual. 

2. “Happy Gilmore” (1996)

If you had to change the core of who you are in order to create enough income to survive, would you be able to do it? Adam Sandler’s “Happy Gilmore” explores this struggle hilariously. “Happy Gilmore (Adam Sandler) lives and breathes hockey. So, you can imagine how devastated he was getting kicked off the team for his powerful yet uncontrolled slapshot, which to Happy’s surprise, translates into the world’s most powerful golf drive, landing him in the PGA. Happy must now shake his rough-and-tumble, hockey-player mentality and learn the poise of professional golf,” writes Hulu.

“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,” shares The Manual.

Who really wants to watch a movie about golf? Sandler actually makes it enjoyable. “Happy Gilmore is one of Sandler’s better-known comedies, and, for some, their favorite sports movie ever, so it’s no surprise that this film makes his top ten,” adds Movie Web. “The film follows Happy Gilmore, a man who desperately wants to make it big as a hockey player, but figures out that golf is actually his forte. When his mother tells him she’s about to lose her house, Gilmore does the logical thing and enters an elite golf tournament with the hopes of winning the cash prize. He quickly becomes a fan favorite due to his brash attitude and foul language, and the movie is truly great if you need a good laugh.”

3. “Billy Madison” (1995)

Watching Sandler play the titular role in Billy Madison is pure bliss. “Born into extreme privilege, Billy Madison hasn’t had to work hard for anything in his life — he didn’t even finish grade school. When Billy’s father presents him with the shocking decision to keep him out of the will, Billy must now prove himself by repeating grades 1 – 12 all over again,” writes Hulu.

"Happy Gilmore" / "Billy Madison" Double Feature
“Happy Gilmore” / “Billy Madison” Double Feature

No one cares if the movie premise is unrealistic, it’s Adam Sandler, we just roll with it. “In Billy Madison, Sandler plays the titular spoiled and childish (or childlike, if you’re generous) hotel heir whose anticipated elevation to head of his father’s company becomes contingent upon him going back to school. Specifically, upon finding out that his father’s wealth and power allowed the now-grown Billy to skate by unearned, Sandler’s shenanigans-prone character must repeat—and pass—grades K–12 in six weeks,” mentions EW. 

“Adam Sandler’s breakthrough performance sees him as a super-rich manchild who somehow cons everyone into believing he’s charming and endearing,” notes Esquire.

4. “Punch-Drunk Love” (2002)

Adam Sandler gets to flex his chops in the romantic comedy genre with “Punch Drunk Love,” and fans were delighted by it. “In this romantic dark comedy, Adam Sandler plays Barry Egan — a socially awkward man with strong repressed emotions and anger issues. In an effort to alleviate his loneliness and self-loathing, Barry gets himself into deep trouble but also finds unconditional love along the way,” describes Hulu.

"Punch-Drunk Love" (2002)
“Punch-Drunk Love” (2002)

Exploring love through awkwardness seems to be a strength of Adam Sandler’s characters. “Paul Thomas Anderson, in all his cleverness, decided to take the Sandler comedic persona and see how it played in one of his films. Here, his anger is scary, his emotional stuntedness disconcerting. Sure, it’s also still a romantic comedy, or maybe a romantic drama, but this was the first time Sandler really stretched his legs. Plus, Philip Seymour Hoffman is in it, and Anderson and Hoffman never failed together,” shares Yardbarker.

This movie proves that all a man needs to flourish is the love of a strong woman. “A simple love story between a squirmy milquetoast (Sandler) on the verge and the woman (Emily Watson) who yanks him back to life, Punch-Drunk Love is as confounding as it is a delight, an expression of unmitigated, sputtering passion—sad and febrile and, most importantly, optimistic about what anyone is truly capable of doing,” adds Paste.

5. “Uncut Gems” (2019)

“Uncut Gems” was a standout movie for Sandler because it completely broke the mold for his capabilities. “Sandler disappears into Howard Ratner’s self-destructive yet ever-hopeful and sweaty skin like he’s never done in any film, and watching Howard’s downward spiral evokes familiar and heightened undertones of the actor’s career-long run of portraying immature men with outsize dreams. Except this time, there’s no soft and silly place to land when things fall apart,” writes EW.

"Uncut Gems" (2019)
“Uncut Gems” (2019)

I bet you never thought you would see Adam Sandler play a villain. “Uncut Gems is different because while it’s clear the Safdie brothers, who grew up on Sandler, care about him and his acting a great deal, they decided to use his power for evil instead of good. Well, maybe not evil — but at least cynical where he would normally be idealistic,” says Vulture.

Forget about that warm and fuzzy feeling you usually get when watching Adam Sandler films. “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,” raves The Manual.

Which character was Adam Sandler’s best performance? Leave a comment to let us know!

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Note: This article was not paid for nor sponsored. StudyFinds is not connected to nor partnered with any of the brands mentioned and receives no compensation for its recommendations.

About Te-Erika Patterson

Te-Erika is the Publisher of The Feisty News for Women, the only full-service news source for women. Te-Erika is also the author of How To Love a Powerful Woman, Leave Your Baby Daddy and Loving Female Led Relationships: Relationships that Empower Women. A graduate of The University of Florida, Te-Erika enjoys a thriving career as a digital content creator that has spanned more than a decade. She enjoys chocolate, wine and solitude, and she is currently living a quiet life in Montgomery, Alabama. Follow her @Te-Erika

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