Adam Sandler’s Cinematic Journey: Ranking the Top 25 Movies from Best to Least Preferred

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There are few actors as renowned as Adam Sandler when it comes to comedy. The 1990s, early 2000s, and even early 2010s were primarily dominated by some of the world's funniest movies, mainly due to Sandler’s performances.

Adam Sandler is the quintessential actor who can put a smile on nearly anyone’s face with his one-liners and goofy personas. He can turn any premise and idea into a joyous adventure with a hefty dose of laughter.

Here are the top 25 best Adam Sandler movies ever released. Read on to find out where to watch some of the best, funniest movies ever.

1 – The Waterboy (1998)

The Waterboy Adam Sandler Kathy Bates Henry Winkler
Image Credit: Buena Vista Pictures Distribution.

If there is one movie to watch to see the full scope of Adam Sandler in a single film, The Waterboy is the one to watch. The story of a boy who wishes to join a football team but is relegated to a disgraceful position has the funniest moments in Sandler’s career.

While it shows its age somewhat in some of its punchlines and jokes, this movie is begged to be rewatched repeatedly.

2 – The Wedding Singer (1998)

The Wedding Singer Adam Sandler Drew Barrymore Christine Taylor
Image Credit: New Line Cinema.

The Wedding Singer is one of the best Adam Sandler movies and one of the best wedding-themed films of all time. Sandler’s wedding singer character’s attempts to win over an upcoming bride engross in the relationship between the two leads and its strong balance of romance and comedy.

3 – The Meyerowitz Stories (2017)

The Meyerowitz Stories Adam Sandler Grace Van Patten Dustin Hoffman
Image Credit: Netflix.

One of the most unique Adam Sandler movies, this comedy sees the beloved actor take a backseat as one of the co-stars in this story of a family and their personal issues as they navigate reuniting with their father. While bittersweet in tone at times, it is also a comedy, showing a more reserved and far more effective use of Sandler’s talent.

4 – 50 First Dates (2004)

50 First Dates Adam Sandler Drew Barrymore Rob Schneider
Image Credit: Columbia Pictures Industries, Inc.

The premise alone is a winner for 50 First Dates as Adam Sandler plays the charming Henry who tries to romance Drew Barrymore’s Lucy every day due to her perpetually thinking she is living the same day repeatedly. This is one of the best feel-good movies from Sandler’s career that happens to be quite funny, too.

5 – Billy Madison (1995)

Billy Madison Adam Sandler Darren McGavin Bridgette Wilson-Sampras
Image Credit: Universal Pictures.

Billy Madison’s premise is just as bonkers as the leading role that Adam Sandler plays in the movie. Starring as a rich kid who now has to go through the K-12 education system in half a year, Sandler is flexible in matching the energy of each class he joins.

6 – Big Daddy (1999)

Big Daddy Adam Sandler Joey Lauren Adams Jon Stewart
Image Credit: Columbia Pictures Inc.

Big Daddy is one of the most formative movies in Adam Sandler’s career as a desperate man who adopts a kid simply to win back the woman he loves. But, of course, nothing goes his way, and he learns the importance and hilarious struggles of being a single father.

7 – Reign Over Me (2007)

Reign Over Me Adam Sandler Don Cheadle Jada Pinkett Smith
Image Credit: Columbia Pictures Industries, Inc. / Sony Pictures Entertainment Inc.

Few times in his storied career has Adam Sandler taken the risk of doing a more serious film that turned out well. Enter Reign Over Me, the one exception to this rule; a tale about a man trying to recover from the grief of losing his family and his friend’s attempt to help him.

It is riveting and unlike anything Adam Sandler has done before or after.

8 – The Longest Yard (2005)

The Longest Yard Adam Sandler Burt Reynolds Chris Rock
Image Credit: Paramount Pictures.

After all of Adam Sandler's antics, The Longest Yard puts him in one of the trickiest spots ever: prison. Leading a group of inmates to rally a football team together to take on the corrupt wardens is just as much one of the funniest Sandler movies as it is heartfelt.

9 – Grown Ups (2010)

Grown Ups Adam Sandler Salma Hayek Kevin James
Image Credits: Columbia TriStar Marketing Group, Inc.

When it comes to a classic Adam Sandler movie that is the definition of his comedic styling, Grown Ups is the one. Sandler excels in this family-friendly comedic drama about himself and his two friends bringing their families together for a celebration.

With a massive cast of comedy legends like Kevin James and Chris Rock, this movie is fun for the entire family.

10 – Just Go With It (2011)

Just Go With It Adam Sandler Jennifer Aniston Brooklyn Decker
Image Credit: Sony Pictures.

This classic romantic comedy about Adam Sandler trying to woo the girl of his dreams leads to an unlikely relationship with his assistant, played by Jennifer Aniston. When it comes to romance films for Sandler, his onscreen relationship with Aniston is the strongest, as she is one of the few to match his energy.

11 – Spanglish (2004)

Spanglish Adam Sandler Téa Leoni Paz Vega
Image Credit: Columbia Pictures Industries, Inc.

Its premise is odd today, but Spanglish is one of the more original funny family movies you can watch. With a housekeeper moving into Sandler’s well-off home, the entire family is turned upside down as kids, parents, and everyone clash in hilarious ways.

12 – Funny People (2009)

Funny People Adam Sandler Seth Rogen Leslie Mann
Image Credit: Universal Pictures.

Funny People is one of the most tonally unique films for Adam Sandler. The balance between comedy and tragedy is unique, forcing Sandler to use his full range. It’s also worth watching for the fascinating relationship between Sandler and Seth Rogen’s characters.

13 – Happy Gilmore (1996)

Happy Gilmore Adam Sandler Christopher McDonald Julie Bowen
Image Credit: Universal Pictures.

Adam Sandler’s take on sports is a unique one, to say the least. As the titular Happy Gilmore, Sandler finds skill in being an unconventional golf player who shocks the scene in his attempts to win enough money to buy his grandmother’s house. This movie has some of the best and most memorable Sandler scenes.

14 – Punch-Drunk Love (2002)

Punch-Drunk Love Adam Sandler Emily Watson Philip Seymour Hoffman
Image Credit: Columbia Pictures.

The tone of Punch-Drunk Love is so far removed from all of the other romantic comedy films Sandler is in. Instead, it is gritty and mature in an adult way, allowing him to show his genuine comedic flair unabashedly while engaging in a strange but compelling romantic relationship.

15 – Hustle (2022)

Hustle Adam Sandler Queen Latifah Juancho Hernangomez
Image Credit: Netflix.

Hustle is one of the better Netflix movies that Adam Sandler helped produce, taking a step in the serious drama direction. The mix of sports and adult drama is intriguing and primarily worth watching, even if it doesn’t necessarily push Sandler to his acting limits.

16 – Anger Management (2003)

Anger Management Jack Nicholson Adam Sandler Marisa Tomei
Image Credit: Columbia Pictures Industries.

Anger Management is one of the Adam Sandler movies that has aged not quite as well as viewers may remember. Sandler and Jack Nicholson have a dueling rivalry with one another that is as fascinating as it is toxic, which is why you should mainly watch this movie today.

17 – Uncut Gems (2019)

Uncut Gems Adam Sandler Julia Fox Idina Menzel
Image Credit: Netflix.

If you can ignore the memes from this movie for a moment, it is one of the unique comedies to come out of Adam Sandler’s career. Equal parts comedy and action, this is one movie that will make you laugh one minute and experience heart-pounding action the next.

18 – Hotel Transylvania 3: Summer Vacation (2018)

Hotel Transylvania 3: Summer Vacation Adam Sandler Andy Samberg Selena Gomez
Image Credit: Sony Pictures Entertainment Inc.

The third entry in the animated monster series is somehow the best, as Count Dracula and his family take a trip on a luxury cruise ship. With a large, fantastic cast of characters who bring out the best of Sandler’s voice, this is one wild ride worth experiencing with the whole family.

19 – Hotel Transylvania 2 (2015)

Hotel Transylvania 2 Adam Sandler Andy Samberg Selena Gomez
Image Credit: Sony Pictures Animation.

Somehow, Adam Sandler’s return to the role of Count Dracula in animated form is better than the original. With a tighter focus, as the hotel is open to anyone and everyone, viewers get to see the fantastic relationship and its growing pains between Dracula and his grandson, Dennis.

20 -Bedtime Stories (2008)

Bedtime Stories Adam Sandler Keri Russell Courteney Cox
Image Credit: Walt Disney Studios
Motion Pictures.

While its effects may not be the most impressive these days, there is something whimsical and magical about Bedtime Stories. The story of Sandler’s character trying to impress his niece and nephew with wild stories that somehow come true is as ridiculous as it is enjoyable to watch.

21- I Now Pronounce You Chuck and Larry (2007)

I Now Pronounce You Chuck and Larry Adam Sandler Kevin James Jessica Biel
Image Credit: Universal Pictures.

There is a reason that Kevin James and Adam Sandler star in so many movies together, and it primarily started because of the hilarious I Now Pronounce You Chuck and Larry. Though its premise is a bit odd in the present-day culture and the film hasn’t aged the best over the years, Sandler and James’ chemistry with one another is undeniable.

22 – Hotel Transylvania (2012)

Hotel Transylvania Adam Sandler Kevin James Andy Samberg
Image Credit: Sony Pictures Entertainment Inc.

One of the few examples of a solid animated film from Adam Sandler’s long career is the traditional family-spooky comedy Hotel Transylvania. Sandler is the lavish and charming Count Dracula with a comedic twist as the host of a hotel for monsters to gather at.

23 – Hubie Halloween (2020)

Hubie Halloween Adam Sandler Kevin James Julie Bowen
Image Credit: Netflix.

Hubie Halloween finds itself as one of the lesser Adam Sandler Netflix releases. The movie follows Sandler on Halloween, forced to investigate a murder amidst antics, pranks, and one-liners. It’s a fun Halloween movie that is at least worth one watch.

24 – Click (2006)

Click Adam Sandler Kate Beckinsale Christopher Walken
Image Credit: Sony Pictures.

In many ways, Click’s most significant issue is trying to be like some of the best movies of all time, dealing with time travel, reliving moments repeatedly, and blending them together. While it lacks some because of doing too much, Sandler is still unforgettable as a man with the power of time and his family’s future in his hands.

25 – Murder Mystery (2019)

Murder Mystery Adam Sandler Jennifer Aniston Mark Strong
Image Credit: Netflix/Scott Yamano.

Adam Sandler and Jennifer Aniston are reunited in unlikely circumstances as the stars of a movie featuring a couple who go on vacation only to find themselves as the lead culprits in a recent murder. Its main struggle is never finding the right balance between drama, mystery, and comedy, but it remains a decent watch at least once.

Author: Cody Perez

Bio:

Copywriter, experienced editor, website creator, PR associate, consultant

  • Expertise: Gaming, Pokémon, movies, TV shows, PR, and creative writing
  • Education: BS in Business Economics (specializing in Business Management), minor in Japanese from Tokyo International University
  • Helped lead or create websites, such as GameRevolution, VGR, RPGInformer, MangaInsider, FandomPost, POKUniverse, and more.
  • Helped launch various indie video games, tech startups, and consulted for YouTube Shorts
  • Writer in the entertainment industry since starting in high school in 2011

Experience: Cody Perez started his career as a journalist and creative writer in the tech and gaming spaces in 2011 while in the middle of high school. Since then, he has produced thousands of high-quality, researched articles for some of the largest entertainment websites in the world, including IGN, Destructoid, Siliconera, Digital Trends, DotEsports, and many more. He also was the lead editor at GameRevolution, growing the site to reach its consistent, historical peak of 8 million MUV the entire time he worked there. Cody also helped launch various successful sites, such as VGR (2 million MUV in a year), POKUniverse, and RPGInformer.

Cody brings together his passion for tech and gaming to his work life, so he can enjoy his hobbies nearly 24/7. He has now taken his expertise and experience with subjects like gaming and Pokémon to Wealth of Geeks, where he is often found creating new lists and reviews, or editing older content to bring it up to the company standard.