Adam Sandler is one of the greatest actors of all time. The guy can do it all, from making us laugh, to cry, to freak out, and everything in between., He's a singular artist who has a voice that continues to change and experiment well into the third decade of his career.

If he's in a movie, I seek it out. I want to know what he's up to, and I'm excited to see him on the big screen.

Today, I want to go over ten of his movies that I think are the best. These are my personal favorites, so it's all subjective.

Let's dive in.

1. Uncut Gems (2019)

  • Directors: Josh Safdie, Benny Safdie
  • Writers: Ronald Bronstein, Josh Safdie, Benny Safdie
  • Cast: Adam Sandler, LaKeith Stanfield, Julia Fox, Kevin Garnett, Idina Menzel, Eric Bogosian

A two-hour-long anxiety attack in the best way possible. The ride is so insane and wonderful, it's just a set of weird twists and turns of people betting on themselves and being jerks, and you go nuts.

Uncut Gems features Adam Sandler's greatest performance to date. As the gambling-addicted jeweler Howard Ratner, he is a magnetic, chaotic force of nature. The film is a masterfully crafted thriller from the Safdie brothers, and Sandler's manic, desperate, and utterly captivating performance is the engine that drives it. It's a career-defining role that earned him widespread critical acclaim and proved he is one of the most versatile actors of his generation.

2. Punch-Drunk Love (2002)

  • Director: Paul Thomas Anderson
  • Writer: Paul Thomas Anderson
  • Cast: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzmán, Mary Lynn Rajskub

This is the film that made critics sit up and take notice. Director Paul Thomas Anderson brilliantly harnesses Sandler's trademark suppressed anger and vulnerability for this artful, anxious, and surprisingly sweet romance.

As the lonely, overwhelmed Barry Egan, Sandler gives a performance that is both unsettling and deeply moving. It legitimized him as a serious actor.

3. Happy Gilmore (1996)

  • Director: Dennis Dugan
  • Writers: Tim Herlihy, Adam Sandler
  • Cast: Adam Sandler, Christopher McDonald, Julie Bowen, Carl Weathers, Frances Bay

Arguably the quintessential '90s Sandler comedy. The concept of a failed hockey player channeling his aggression to become a golf prodigy is comic genius.

And this movie might be the best showcase of how funny he can be. He carries every scene and makes you buy into a premise that is laugh out loud.

The film is a perfect storm of hilarious rage, iconic supporting characters (Shooter McGavin, Bob Barker), and unforgettable lines. "The price is wrong, b*tch!" is forever etched in cinematic history.

4. The Wedding Singer (1998)

  • Director: Frank Coraci
  • Writer: Tim Herlihy
  • Cast: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert, Angela Featherstone

This movie is charming. It never ceases to make me smile. It's so sweet and energetic.

This film revealed a new side of Adam Sandler: the romantic lead. There's a killer soundtrack and the undeniable chemistry between Sandler and Drew Barrymore. It’s a sweet, funny, and nostalgic rom-com that proved Sandler's appeal went far beyond slapstick.

5. Billy Madison (1995)

  • Director: Tamra Davis
  • Writers: Tim Herlihy, Adam Sandler
  • Cast: Adam Sandler, Bradley Whitford, Bridgette Wilson, Darren McGavin, Norm Macdonald

"Back to school... back to school... to prove to dad that I'm not a fool." This low-brow movie is so weird. I feel like this is a movie I know is messy and sort of disjointed, but you laugh so hard watching it that it doesn't matter that much.

You're just having fun.

This is the film that truly established the Adam Sandler persona. It's juvenile, endlessly quotable, and unabashedly silly. The story of a rich man-child repeating grades 1-12 is a perfect showcase for his unique brand of chaotic, nonsensical humor that became a touchstone for a generation.

6. Hustle (2022)

  • Director: Jeremiah Zagar
  • Writers: Taylor Materne, Will Fetters
  • Cast: Adam Sandler, Queen Latifah, Juancho Hernangómez, Ben Foster, Robert Duvall

A love letter to the game of basketball, Hustle features one of Sandler's best modern performances.

As a weary NBA scout who discovers a once-in-a-lifetime prospect in Spain, Sandler is grounded, passionate, and deeply authentic. It's a fantastic sports drama that proves his dramatic chops are no fluke, earning him a Screen Actors Guild Award nomination.

7. The Waterboy (1998)

  • Director: Frank Coraci
  • Writers: Tim Herlihy, Adam Sandler
  • Cast: Adam Sandler, Kathy Bates, Henry Winkler, Fairuza Balk, Jerry Reed

I saw this movie on vacation on TNT and I laughed so hard I think I snotted. And now, I still do. It's like a great sports movie about underdogs and has some of the funniest lines.

Perhaps the most purely ridiculous and quotable film of Sandler's '90s peak. His performance as the socially inept, rage-fueled "water distribution engineer" Bobby Boucher is a comedic tour de force. The film is absurd, over-the-top, and a perfect encapsulation of the Happy Madison formula that dominated the box office.

8. 50 First Dates (2004)

  • Director: Peter Segal
  • Writer: George Wing
  • Cast: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Dan Aykroyd, Blake Clark

Reuniting with Drew Barrymore, Sandler struck gold again with this high-concept romantic comedy. He plays a veterinarian in Hawaii who falls for a woman with anterograde amnesia, forcing him to make her fall in love with him again every single day.

The premise is brilliant, and the film succeeds by leaning into the sweetness of their chemistry, creating a rom-com classic that is both funny and incredibly heartfelt.

9. Click (2006)

  • Director: Frank Coraci
  • Writers: Steve Koren, Mark O'Keefe
  • Cast: Adam Sandler, Kate Beckinsale, Christopher Walken, Henry Winkler, David Hasselhoff

The ending of this movie is a downer and will always stick with me, but I also think this movie hits Sandler's ethos and life. He just wants us to enjoy every moment, even the hard ones.

What starts as a high-concept comedy about a man who gets a universal remote that controls his life becomes a surprisingly poignant and emotional story about family and regret. Click showcases Sandler's ability to handle heavier themes. It's a film that has resonated more deeply with audiences as they've grown older.

10. Big Daddy (1999)

  • Director: Dennis Dugan
  • Writers: Steve Franks, Tim Herlihy, Adam Sandler
  • Cast: Adam Sandler, Joey Lauren Adams, Jon Stewart, Cole Sprouse, Dylan Sprouse, Leslie Mann

This movie is absolutely nuts. I firmly believe the reason it works is because you kind of trust Sandler to be a fun Dad and not to hurt a kid. And Sandler knows the way to make this movie work is to give it a ton of heart.

He plays Sonny Koufax, a lazy law school grad who adopts a kid to impress his girlfriend. Sandler finds the perfect vehicle to be both irresponsibly hilarious and genuinely touching. It was a box-office smash and proved he could carry a comedy with a little more substance.

Summing It All Up 

The Sand Man is one of my favorite performers and entertainers. I am so happy to be alive while he's exploring such great characters and making movies that get everyone to lean in. He's truly one of a kind.

Let me know what you think in the comments.

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