Adam Sandler Movies: Best of All Time

For many fans of the best comedy movies, Adam Sandler has been firmly entrenched as one of the top comedy actors of the last twenty years. The the list of Adam Sandler movies includes a large array of straight-forward comedies that have mostly been driven by the unique comedic talents of Sandler himself.

Sandler made a name for himself initially on Saturday Night Live as part of the crew of top comedy actors on the show in the early to mid-1990s. He used his popularity from the show to embark on movie making and soon formed Happy Madison Productions, a studio named after two of his first, and still most popular movies and characters (Billy Madison and Happy Gilmore). This list of Adam Sandler movies is focused on the Top 10 movies with Adam Sandler of all time, beginning in the mid-1990s when he first appeared on prominently on screen.

For the purposes of this top 10 list of Adam Sandler movies, the movie must have been entertaining, well-received commercially and/or critically (where not many Sandler films have been), epic in nature with a lasting impact, iconic in its time, and Sandler must have been a significant player in the film.

Best Adam Sandler Movies of All Time

10. 50 First Dates (2004) – Adam Sandler reunited with his Wedding Singer co-star Drew Barrymore in this romantic comedy about a woman (Barrymore) who suffers from a type of short-term memory that kicks in when she wakes up each morning. This makes it difficult for the pair to build a long-term relationship.

9. I Now Pronounce You Chuck & Larry (2007) – Sandler joined comedy colleague Kevin James (“King of Queens”) in this movie about two men who decide to portray a gay couple for personal reasons, which doesn’t sit well at the fire station.

8. Spanglish (2004) - In a movie that shows off a more mature side to Adam Sandler, Spanglish is a romantic comedy in which a strained relationship between Sandler’s character and his wife (played by Tea Leoni) leads to potential extramarital affairs.

7. Mr. Deeds (2002) – In this movie, Sandler takes on the role of an underachiever who inherits a billion dollar fortune and plenty of “grown up” responsibilities. Winona Ryder plays his love interest, though there is plenty of turmoil.

6. Big Daddy (1999) – People who aren’t as enthusiastic about typical Sandler comedy might appreciate Big Daddy as much or more than any of his other films. This movie not only portrays his comedy style, but it also has a nice story about an ill-equipped man (Sandler) who becomes a father.

5. Anger Management (2003) – In another one of the more mainstream Adam Sandler movies, Anger Management showcases Jack Nicholsan as an anger management teacher who’s very eccentric teaching methods get under Sandler’s character’s skin, but manages to get him to open up. The result is plenty of funny moments.

4. The Waterboy (1998) - Adam Sandler definitely likes to incorporate his passion for sports in his comedy movies. His character Bobby Boucher is an under-educated waterboy for his college football team who learns to channel his pinned-up anger towards his mother to become a dominant force in college football.

3. Wedding Singer (1998) – This particular Adam Sandler movie has perhaps a broader audience because it not only features a Sandler-driven plot, it also delves into the best of the 80s with great 80s music, hair styles, and themes. Drew Barrymore is at her best as the romantic interest for Sandler’s character.

2. Billy Madison (1995) – One of the Adam Sandler originals, Billy Madison is arguable his most iconic film. His character (for which the movie is named) is memorable, and reminiscent of the nature of Sandler comedy.

1. Happy Gilmore (1996) – For true Sandler fans, the debate about the best Adam Sandler movie breaks down to this film or its predecessor, Billy Madison. However, if you appreciate Adam Sandler’s comedy, his character and the story in Happy Gilmore was a bit more entertaining.

No doubt there are great Adam Sandler movies not included in this list. In fact, there are several that could have been comfortably included without reservation. However, the list in place gives a good scope of the legacy of Adam Sandler films that spans about 15 years.

Want to tell us your favorite film not on our list of Adam Sandler movies and why? Just add a comment and share your thoughts!

This feature article about the Best Movies with Adam Sandler was written by Neil of Movie Room Reviews

See also:

• List of Johnny Depp movies
• Best Jim Carrey movies
• Best Will Smith movies