10 Best Romantic Comedy Movies on Amazon Prime Video

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Chasing Amy
Chasing Amy /

1. Chasing Amy (1997)

Director: Kevin Smith

Starring: Ben Affleck, Joey Lauren Adams, Jason Lee, Dwight Ewell, Jason Mewes, Kevin Smith, Ethan Suplee, Casey Affleck, Matt Damon, Scott Mosier

While you might be looking for one of many romantic comedy movies that fits the traditional roles of the genre (the cheap laughs, the predictable plot, Matthew McConaughey), there isn’t a better movie in the genre streaming for free on Amazon Prime Video with a membership than Chasing Amy. Kevin Smith had already made a name for himself with Clerks and Mallrats, but Chasing Amy absolutely delivers on that level if not better.

The movie follows a pair of best friends and comic book artists named Holden and Banky with the former falling hard for a lesbian comic book artist named Alyssa. The two begin dating, but things fall apart when Holden finds out that he’s not the first guy that she’s been with and things progress from there.

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With Jay and Silent Bob also returning to the screen, Chasing Amy is absolutely fantastic in terms of delivering all of the laughs in a real world setting while also giving viewers an untraditional romantic comedy film that will leave a mark on the minds and emotions of anyone who watches it.