Best Adam Sandler Movies: Top 5 Flicks Most Recommended By Experts

We all know Adam Sandler as a famous American comedian, screenwriter, actor, film producer and singer. But way back in 1990, he was first discovered doing stand up comedy and added to the cast of “Saturday Night Live”. Sandler was employed by SNL for the next 5 years until 1995. Soon after, he began to get casted for different movies and became the star we know today. The best Adam Sandler movies are riddled with comedy and usually feature many familiar faces.

Adam Sandler has a gift of making an audience laugh until they cry but also feel deeper emotions too.  When you think of Adam Sandler and his best movies, a variety of characters may come to mind that make you giggle – “Billy Madison”, “Happy Gilmore”, “The Waterboy”. You may also think of Sandler’s softer side – “50 First Dates”, “The Wedding Singer”, “Just Go With It”, “Punch-Drunk Love”. No matter the role that Sandler has played there is a movie to be enjoyed by everyone. 

Plus, finding a movie that gives you the giggles has real benefits. A recent study found that laughter and smiling can help relieve daily stress. Laughing may help a person better handle the stress that occurs in daily life. There isn’t a direct correlation to how hard someone laughs and how stress affects them in that sense. So, turn on your favorite Adam Sandler movie and laugh as your stress melts away!

The endless titles that have come from the beloved comedian make it hard to decide which are among the ultimate greats. That’s why StudyFinds set out to do the research for you, visiting 10 expert websites to put together this list of the best Adam Sandler movies that were recommended across these sites! If you have your own suggestions, please leave them in the comments below!

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 Fans

1. “Uncut Gems” (2019)

On multiple occasions, Adam Sandler has shown that he is not all comedy. “Howard Ratner, the Manhattan jeweler played by Sandler in the Safdie Brothers-directed crime thriller Uncut Gems, believes in his ability to beat the odds. Even when he’s pushing his luck or engaging in self-destructive behavior, Howard displays confidence, a quality Sandler brings to this emotionally challenging, potentially alienating role,” says Thrillist.

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

This is a movie that keeps you at the edge of your seat. Uncut Gems is an incredibly rich, thematically ambitious movie that is able to be told deftly, at a breakneck pace, because of Adam Sandler and the magnitude of both his performance and what he represents,” explains Vulture.

With his performance as Howard Ratner, “Sandler won the Independent Spirit award for this darkly comedic drama about a gambling-addicted jewelry salesman who must keep his life from unraveling as he tries to sell a rare gem,” adds Gold Derby.

It seems like Adam Sandler has continued to pursue different roles since the release and success of the film. “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,” writes The Manual.

2. “Billy Madison” (1995)

Sandler got his start by making a crowd laugh. He continued doing that when “Billy Madison” was released and instantly became a classic comedy that continues to be quoted and watched today. “Sandler’s first proper post-SNL success set the character template he and others would mine, with greater or lesser success, for the next three decades,” explains EW.

"Billy Madison" (1995)
“Billy Madison” (1995)

Some may say that this is the movie that made his name known. “The film that put Adam Sandler’s career on the map, Billy Madison is a beloved ‘90s comedy classic. The film follows the titular hotel heir (Sandler) as he repeats the first through twelfth grades in two weeks to prove to his father (Darren McGavin) that he is worthy of inheriting his empire. Billy Madison gave birth to the Adam Sandler persona as we know it today: Billy is immature, ridiculous, and frequently participates in gross out humor, much to the chagrin of the many adults around him. Sandler quickly became a comedy hero to many young filmgoers with this movie,” adds The Complex.

“Billy Madison” is a movie that continues to bring laughter to a room. “This is Sandler’s man-child masterpiece, full of improvised bits, laugh-out-loud moments, memorable appearances by Norm MacDonald, Chris Farley, and Steve Buscemi, and one that is perfect for re-watches while hanging with friends,” notes MovieWeb.

3. “Happy Gilmore” (1996)

Soon after the success of “Billy Madison”, Happy Gilmore was released the following year. “Billy Madison was already pretty over the top, but Happy Gilmore goes to even more surreal humor with Adam Sandler fighting Bob Barker, who plays himself (‘The price is right, bitch!’). Happy Gilmore won’t turn any hardcore Adam Sandler haters into fans, but it’s Sandler doing what he does best with likable characters and an inspired sense of lunacy,” explains The Complex.

There is no doubt that Adam Sandler can make a room burst out in laughter. “The early stages of a comedian’s career is about finding your clown — the core of what is funny about you — and then acclimating audiences to it. It’s more than finding a persona, because for comedic actors, what is funny about them is constant even if they are playing different characters. Through SNL (which is like clown-finding bootcamp) and his albums, Sandler had a good sense of who he was by the time he made Billy Madison. But it wasn’t until Happy Gilmore that he showed a wide audience the full force of the comedic trait that would go one to define him: his anger. In basically every movie that follows, Sandler would expand upon his comedic rage, but in Gilmore it is front and center,” adds Vulture.

“Happy Gilmore” does not bring a typical golf experience to the screen. Happy Gilmore (Sandler) is a hockey reject with the most powerful drive in golf, so he joins the P.G.A. to make some money and save his grandmother’s house. Unfortunately, the hockey player mentality and taunting don’t go so well with the upper-class mentality of golf,” says MovieWeb.

4. “The Wedding Singer” (1998)

Just two years after the character “Happy Gilmore” kept us all laughing, “The Wedding Singer” was released. “One of the better romantic comedies of our generation, The Wedding Singer is a genuine, sweet story of a boy who meets and falls for a girl, but realizes he can’t have her,” says The Manual.

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

It is always amazing to see chemistry between actors that feels natural and true. “The Wedding Singer” gives the audience just that with Sandler and Drew Barrymore, who have gone on to do other films together. “The Wedding Singer is a cute, romantic film where Sandler proved he could be a charismatic, romantic leading man. His partnering with Barrymore makes him better, as he’s more present and they have believable chemistry, thanks to her abilities. That’s why they worked together again on 50 First Dates and Blended. The Wedding Singer is a bit more grown-up movie for Sandler; there are dumb jokes, but they’re not the center of the film, they’re an add-on while showing what it means to grow up, even if it’s on your own terms, giving us one of the best marriage proposals of all time,” adds Movieweb

It was very clear that Adam Sandler was a great comedian, but the softer side of him caught many by surprise. “The Wedding Singer was the first evidence that Sandler had range and could use our idea of the types of characters he usually plays to surprise us,” mentions Complex

Many agree that “The Wedding Singer” showed how incredible of an actor he is. Ironically, this was Sandler’s most mature work to date, if not ever. Comedically, he’s strong, but instead of his lowbrow/annoying instincts, you get clever ’80s jokes (pioneering a cottage industry of ’80s reference comedy). And it’s incredible how good he is in this film. It’s our first glimpse of him as an actual actor,” raves Vulture.

5. “Punch-Drunk Love” (2002)

In the early 2000s, Adam Sandler had been seen in many memorable movies. It has to be a really great feeling as an actor when character roles are written with you in mind. Not only was this role written for him, but Adam Sandler was also nominated for awards for the role. “Sandler earned a Golden Globe Nomination for Best Actor in a Comedy or Musical for this film from writer director Paul Thomas Anderson,” says Gold Derby.

The character Barry Egan was written specifically with Sandler in mind. “The first director to intuit just what Adam Sandler could do with a character tailored to his raw comic energy, Paul Thomas Anderson wrote Punch-Drunk Love‘s main character Barry Egan for Sandler,” writes EW.

“Punch-Drunk Love” quickly became one of the most memorable movies of the 2000s. “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” explains Paste Magazine.

Adam Sandler has played many characters that are well loved, but the character of Barry Egan captured an introvert beautifully. “It’s hard for a film and actor to capture an introvert, since a movie sort of needs its main character to interact with the world, but Sandler is incredible at playing a person who doesn’t want to be looked at but you can’t keep your eyes off of,” adds Vulture.

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