8. The Wedding Singer (1998)
The majority of Adam Sandler’s movies are considered at least marginally divisive, but when it comes to comedy, the Sandman really does know his stuff. The Wedding Singer marked the first on-screen pairing of Sandler and Drew Barrymore in a tragically underrated musical rom-com. In case you couldn’t tell, we love The Wedding Singer.
On paper, it plays to all of Sandler’s strengths. He plays a slightly tragic but incredibly sweet guy, he gets to use his beautiful singing voice, and he also has the opportunity to scream incoherently on at least one occasion. Basically, it’s a Sandler slam dunk.
More than that, The Wedding Singer is one of the ’90s best comedies because of the excellent chemistry between its stars. The Sandler-Barrymore effect was re-employed twice more in subsequent decades, so undeniable is their spark. The Wedding Singer remains one of Sandler’s best (and most overlooked) movies to this day.