10 Best Adam Sandler Movies, Ranked

Okay, let’s talk Adam Sandler. He’s truly one of a kind in Hollywood. I remember when he first broke out on Saturday Night Live – he was instantly hilarious. Then, boom, he became a massive movie star, practically owning the comedy scene in the 90s and early 2000s. His early films were… different. Really silly, with these wild, over-the-top moments and a total willingness to be absurd. Critics weren’t always kind, calling it lowbrow humor, but honestly, audiences connected with it. There was a surprising amount of heart under all the goofiness and slapstick. And over the years, he built Happy Madison Productions, which became a hit-making machine, letting him work with his friends and consistently give people what they wanted: a good time.

While Adam Sandler is well-known for his comedies, focusing only on those films overlooks his impressive dramatic talent. He consistently surprises audiences and critics with powerful, nuanced performances, stepping away from his usual comedic style every few years. He’s also collaborated with highly acclaimed directors, demonstrating that the actor behind silly songs is capable of leading serious, character-driven films. This combination of lighthearted and intense roles makes his body of work particularly fascinating, constantly shifting between easy entertainment and gripping drama.

10) The Waterboy

Sports comedies were hugely popular in the late 1990s, and The Waterboy is one of the most successful examples. The film stars Adam Sandler as Bobby Boucher, a socially awkward water boy who unexpectedly turns out to be an incredibly powerful tackler. He joins the South Central Louisiana State University Mud Dogs, coached by the quirky Coach Klein (Henry Winkler), and tries to lead them to victory. While the story is a classic underdog tale, the movie works because of Sandler’s dedicated performance and Kathy Bates’ hilarious portrayal of his overbearing mother. It’s full of memorable lines and has a cartoonish style that makes the hard-hitting football scenes funny instead of violent. The Waterboy showcases Sandler at his best with physical comedy, creating a character who is ridiculous but still easy to cheer for.

9) 50 First Dates

It’s rare for actors to recapture their magic when they work together again, but Adam Sandler and Drew Barrymore proved their connection was real in 50 First Dates. Sandler plays a Hawaiian vet who falls in love with Lucy (Barrymore), only to learn she has a condition that causes her to lose her memory every day. Instead of walking away, he chooses to win her heart anew each morning, leading to sweet and inventive displays of affection. The movie skillfully blends humor with the sadness of Lucy’s situation, creating a romantic comedy that feels genuinely heartfelt. Sandler also tones down his typically over-the-top energy, letting the romance be the focus. Notably, the film avoids an easy, magical fix, opting for a realistic ending, which makes it one of the more thoughtful stories from Sandler’s production company.

8) Big Daddy

For Adam Sandler to move from silly college-style comedy to more mature roles, Big Daddy was the ideal film. He plays Sonny, a carefree law school grad who pretends to adopt a five-year-old, Julian, to win over his girlfriend. When she leaves him, Sonny unexpectedly becomes a parent and learns there’s more to life than just having fun. The movie works so well because Sandler gets to keep his playful, rebellious side while dealing with a child who copies his antics. This creates a funny and heartwarming relationship, particularly when Sonny fights to legally adopt Julian. Big Daddy proved Sandler could handle more emotional moments without losing the goofy charm that made him famous, making it one of his most successful and beloved films.

7) Hustle

Netflix is known for Adam Sandler’s comedies, but Hustle is different – it’s a heartfelt sports drama about basketball. Sandler plays Stanley Sugarman, a tired talent scout for the Philadelphia 76ers, who finds a promising player named Bo Cruz (Juancho Hernangómez) in Spain. Stanley takes a chance on Bo, bringing him to the US and training him for the NBA draft, despite doubts from the team owner (Ben Foster). The movie avoids a negative portrayal of the sports world and instead celebrates the love of the game, featuring appearances from many real NBA players. Sandler gives a compelling performance as Stanley, a man who’s worn down but deeply passionate about basketball, making Hustle an inspiring story that has resonated with both viewers and critics.

6) The Meyerowitz Stories (New and Selected)

Noah Baumbach, a director known for realistic conversations and complicated families, really found a great actor in Adam Sandler for the film The Meyerowitz Stories (New and Selected). The movie centers on the children of Harold Meyerowitz (Dustin Hoffman), a father who is an artist and has a big influence on his kids. Sandler plays Danny, the oldest son, who always felt overlooked, especially compared to his more accomplished half-brother, Matthew (Ben Stiller). Sandler’s performance is subtle and honest, perfectly showing the sadness of a man who just wants his father’s approval, but his father can’t seem to give it. He also impressively acts alongside veteran stars like Hoffman and Emma Thompson, portraying a character filled with lifelong insecurity. The Meyerowitz Stories demonstrates Sandler’s talent for playing flawed characters with a depth that you don’t often see in his comedic roles.

5) Billy Madison

Every iconic actor has a breakout role, and for Adam Sandler, that movie was Billy Madison. The film cemented the goofy, playful style he’s known for. Sandler plays Billy Madison, a spoiled rich kid who has to retake all 12 grades of school in just 24 weeks to prove he deserves to take over his family’s hotel business. The story is totally ridiculous, which allowed for over-the-top humor – think a huge penguin, a scary bus driver played by Chris Farley, and a song about passing third grade. When it first came out, critics didn’t understand the movie’s silliness, but it quickly became a fan favorite thanks to its wild, unpredictable energy. Billy Madison is pure, unfiltered fun, with Sandler giving a performance that’s both lovable and annoying. It essentially created the blueprint for the lovable man-child characters he’d play in many films over the next ten years.

4) Happy Gilmore

Following the success of his earlier film, Happy Gilmore took the wild and energetic character style of Billy Madison and focused it on the refined world of professional golf. Adam Sandler plays a former hockey player who finds out he has an incredible golf drive – he can hit the ball 400 yards! He uses this talent to join the PGA tour and try to save his grandmother’s home. The movie is funny because it contrasts the working-class, easily angered Happy with the arrogant Shooter McGavin (Christopher McDonald). The humor comes from Happy’s rough behavior clashing with the proper rules of golf. Plus, the film has one of the most memorable cameos ever – a hilarious fight between Happy and game show host Bob Barker. Happy Gilmore is still considered one of Sandler’s best comedies, successfully combining both anger and heartfelt emotion in a way he hasn’t quite matched since.

3) The Wedding Singer

Released in the vibrant 1980s, The Wedding Singer established Adam Sandler as a leading man in romantic comedies. The film follows Robbie Hart (Sandler), a kind-hearted wedding singer whose world falls apart when his own wedding is called off. He finds a connection with Julia Sullivan (Drew Barrymore), a waitress trapped in a relationship with an unfaithful man. While filled with 80s references, the movie’s story of love and heartbreak remains relatable. Sandler also showcases his musical ability with heartfelt original songs, like “Grow Old With You.” The Wedding Singer is a charming and honest film that showed a softer, more vulnerable side of Sandler, instantly winning over audiences.

2) Punch-Drunk Love

Paul Thomas Anderson recognized a hidden talent in Adam Sandler, leading to the critically acclaimed film Punch-Drunk Love. The movie centers on Barry Egan, played by Sandler, a solitary salesman of novelty plungers who is constantly harassed by his seven sisters. His life takes a turn when he meets Lena Leonard (Emily Watson), and he begins to assert himself, even as he gets caught up in an extortion scheme orchestrated by a mattress salesman (Philip Seymour Hoffman). Anderson expertly taps into Sandler’s underlying intensity to portray a man dangerously close to a breakdown. It’s a frightening and heartbreaking performance, moving beyond comedy to reveal the damaging effects of bottled-up anger. Punch-Drunk Love completely changed how audiences viewed Sandler, demonstrating his ability to deliver truly artistic work.

1) Uncut Gems

Adam Sandler gave what many consider the best performance of his career in the Safdie brothers’ intense thriller, Uncut Gems. He plays Howard Ratner, a wildly chaotic jeweler in New York City who’s addicted to gambling and risks everything on selling a unique black opal. The movie is a constant, overwhelming experience, putting the audience right inside Howard’s stressful life as he deals with dangerous lenders, an affair, and upset basketball players. Sandler is captivating as a character who’s difficult to like, but impossible to look away from. He portrays Howard with a desperate hopefulness, always believing a big win is within reach, and this energy powers one of the most anxiety-inducing films ever made. Uncut Gems is exceptional because it showcases Sandler’s full range as an actor, creating a truly memorable and tragic character.

What’s your favorite Adam Sandler movie? Share your pick in the comments and join the discussion on the ComicBook Forum!

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2025-12-17 20:17