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Best Adam Sandler Movies: A Guide to His Most Iconic Films

Adam Sandler is one of those actors who has carved out a unique space in Hollywood. Whether you love his goofy humor or his surprisingly deep dramatic performances, there’s no denying his impact on the film industry. From slapstick comedies to heartfelt dramas, Sandler has delivered a wide range of performances over the years. If you’re looking for a movie marathon or just want to check out his best work, you’re in the right place.

The Evolution of Adam Sandler’s Career

Before we jump into the list of his best movies, let’s take a quick look at how Sandler became the household name he is today.

  • Early Days: Sandler started as a stand-up comedian and then joined Saturday Night Live (SNL) in the early ’90s, where his quirky characters and hilarious songs made him a fan favorite.
  • Comedy King: Movies like Billy Madison and Happy Gilmore established him as a comedy star.
  • Dramatic Turns: Films like Punch-Drunk Love and Uncut Gems proved his versatility as an actor.

Now, let’s dive into the movies that have defined his career.

1. Happy Gilmore (1996)

If there’s one movie that perfectly captures Adam Sandler’s comedic style, it’s Happy Gilmore. Sandler plays a failed hockey player who discovers a hidden talent for golf. The movie’s ridiculous premise, memorable quotes, and the iconic fight with Bob Barker make it a must-watch.

Why it stands out:

  • Classic one-liners like “The price is wrong, Bob!”
  • A perfect blend of absurd humor and heart
  • Introduced audiences to Sandler’s signature anger-fueled comedy

Box Office: $41 million (not bad for a quirky golf movie!)

2. The Wedding Singer (1998)

Set in the 1980s, The Wedding Singer showcases Sandler’s softer, romantic side. His chemistry with Drew Barrymore is undeniable, and the nostalgic soundtrack makes it even more enjoyable.

Why it stands out:

  • Sandler’s first foray into romantic comedy
  • Drew Barrymore and Sandler’s on-screen magic
  • The heartfelt song “Grow Old With You”

This movie proved Sandler could do more than just yell and break things—he could make us swoon, too.

3. Big Daddy (1999)

Big Daddy mixes comedy with genuine emotion as Sandler’s character suddenly finds himself raising a young boy. The movie explores themes of responsibility, maturity, and the bond between a father figure and a child.

Key elements:

  • The adorable performance by Dylan and Cole Sprouse
  • Classic Sandler humor with a heartfelt twist
  • A surprisingly touching story about growing up

4. Punch-Drunk Love (2002)

Paul Thomas Anderson’s Punch-Drunk Love was a game-changer for Sandler. Known primarily for comedies, he shocked audiences with his intense and vulnerable performance.

What makes it special:

  • Sandler’s first major dramatic role
  • Unique, artistic direction by PTA
  • A romantic story that feels raw and real

If you thought Sandler was just a goofball, this movie will change your mind.

5. 50 First Dates (2004)

Sandler teamed up with Drew Barrymore again for this charming romantic comedy about a woman with short-term memory loss.

Why it’s a fan favorite:

  • Heartwarming and funny
  • Beautiful Hawaiian backdrop
  • A mix of Sandler’s humor with genuine emotion

6. The Longest Yard (2005)

In this remake of the 1974 classic, Sandler plays a former NFL quarterback who leads a prison football team against the guards.

Aspect Details
Genre Sports Comedy
Co-stars Chris Rock, Burt Reynolds
Box Office $190 million worldwide

What stands out:

  • A solid blend of humor and action
  • Great ensemble cast
  • Perfect for sports and comedy fans alike

7. Click (2006)

Who knew a remote control could make you cry? Click starts as a typical Sandler comedy but turns into a surprisingly emotional tale about family and life’s fleeting moments.

Why it resonates:

  • A unique, relatable premise
  • A mix of humor and heart
  • A reminder to appreciate the present

8. Uncut Gems (2019)

If you haven’t seen Uncut Gems, prepare yourself for a nerve-wracking experience. Sandler plays Howard Ratner, a New York jeweler with a gambling addiction who finds himself in over his head.

Why it’s a must-see:

  • Sandler’s best performance to date
  • Intense, edge-of-your-seat storytelling
  • A gritty, realistic look at addiction and ambition

The Safdie Brothers brought out a side of Sandler that many didn’t know existed.

9. Murder Mystery (2019)

Teaming up with Jennifer Aniston, Sandler delivers a light-hearted, globe-trotting comedy in Murder Mystery. It became one of Netflix’s most-watched movies.

What makes it fun:

  • Exotic European locations
  • Classic whodunit mystery with a comedic twist
  • The easy chemistry between Sandler and Aniston

10. Hustle (2022)

In Hustle, Sandler plays a down-on-his-luck basketball scout who discovers a talented player in Spain. It’s another reminder that Sandler’s acting chops go beyond comedy.

Highlights:

  • A love letter to basketball
  • A compelling underdog story
  • One of Sandler’s most grounded performances

Honorable Mentions

While these ten movies represent the best of Sandler’s career, there are plenty more worth watching. Here’s a quick list of honorable mentions:

  • Billy Madison (1995) – The movie that started it all
  • Spanglish (2004) – A mix of drama and comedy
  • Grown Ups (2010) – Classic Sandler ensemble fun
  • Reign Over Me (2007) – A deeply emotional performance

Adam Sandler’s filmography is as diverse as it is entertaining. From laugh-out-loud comedies to thought-provoking dramas, he’s proven time and again that he’s more than just a funny guy. So, whether you’re in the mood for something lighthearted or a movie that hits you right in the feels, Sandler’s got you covered.

What’s your favorite Adam Sandler movie? Let us know in the comments.

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