Last Updated on August 3, 2021
#1- PUNCH-DRUNK LOVE
Paul Thomas Anderson did something with Adam Sandler’s skills that no other filmmaker has tapped into. Subduing Sandler and forcing him to understate ever aspect of his performance resulted in the single best acting job in his entire filmography. PUNCH-DRUNK LOVE is a brilliant and astounding film from one of our best directors and should have garnered an Oscar for Sandler.
#2 – THE WEDDING SINGER
Sandler released two movies in 1998: THE WEDDING SINGER and THE WATERBOY. One was his par for the course toilet comedy and the other was a surprisingly well-done romantic comedy. THE WEDDING SINGER is the film that proved Sandler could be a romantic lead and a character the average guy could relate to. Plus, with his musical background, this film put Sandler’s singing chops to perfect use.
#3 – BULLETPROOF
In the history of buddy cop movies, few are as underrated as this pairing of Damon Wayans and Sandler. Great banter and some well-shot action sequences make this a must see for fans of the genre. Sandler could use a few more movies like this in his career and fans may turn back in his favor.
#4 – AIRHEADS
One of his earliest movie roles, AIRHEADS may be a supporting turn for Sandler but he does a great job in carrying the comedy without going to broad with it. Pip may be an idiot, but he is a lovable one. Brendan Fraser and Steve Buscemi do the heavy lifting here, but Sandler’s contribution is strong.
#5 – HAPPY GILMORE
HAPPY GILMORE is the second feature that cemented Sandler as a Hollywood comedy lead. It is heads and tails better than BILLY MADISON while still keeping the toilet humor intact. Maybe it is the sports theme, which would become common in Sandler’s career, or maybe it is just the fact it doesn’t have to go too over the top, HAPPY GILMORE is another quotable classic.
#6 – HOTEL TRANSYLVANIA
Yes, it may be animated, but HOTEL TRANSYLVANIA is a perfect match for Sandler’s child-like humor. Bringing together his crew of frequent collaborators like Steve Buscemi, David Spade, and Kevin James, this movie delivers a well-scripted tale that features all of the classic movie monsters you know and love. Sandler is great as Dracula and tells his tragic back story beautifully.
#7 – CLICK
While many people discount the early 2000s output from Sandler, CLICK is a gem buried right in the middle of a bunch of garbage. Featuring a unique time travel plot device and a gorgeous Kate Beckinsale, CLICK is a great balance of heart and humor that really deserves a second look.
#8 – BIG DADDY
After THE WEDDING SINGER, Sander’s comedies started to take a more adult twist and tackle more grown-up concepts like parenthood. Coupled with the same toilet humor, Sandler began to act his age, or at least like a man-child his age. BIG DADDY was one of the last good comedies Sandler would appear in for several years.
#9 – BILLY MADISON
Following his success on SNL, Sandler’s first solo feature is ridiculously stupid. The concept of a spoiled rich kid going back through every grade to prove himself to his father is replete with bathroom humor and really poor direction, but damn if it isn’t a heartwarming and fun movie.
#10 – SPANGLISH
The great James L. Brooks knows how to balance comedy and drama. After his award-winning AS GOOD AS IT GETS, Brooks cast Adam Sandler in a dramatic role as a husband and father on the cusp of losing his family. Critics were not always kind to this movie but it was one of the best performances in Sandler’s career.
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