For a film made in the mid-90s, by a straight white man in his early 20s, Chasing Amy is startingly smart and sensitive, filled with more relatable moments than anyone would care to admit. Sure, by today’s standards, its exploration of sexuality is questionable at best and cringe-worthy at worst, but it’s also an honest depiction of how an era (and some people still) confront this reality. And for all the important issues it tries to address, like homophobia, racism, and toxic masculinity, it’s also at its core a confectionary romcom. If When Harry Met Sally asks, “Can women and men be friends?”, then Chasing Amy complicates it with a question of its own: “Can a lesbian and a guy who falls in love too quickly be friends?” You may or may not arrive at an answer by the film’s end, but you’ll find much to like in its earnestness and thoughtfulness.

Genre: Comedy, Drama, Romance

Actor: Ben Affleck, Brian O'Halloran, Carmen Llywelyn, Casey Affleck, Dwight Ewell, Ethan Suplee, Guinevere Turner, Jason Lee, Jason Mewes, Joe Quesada, Joey Lauren Adams, Kevin Smith, Matt Damon, Scott Mosier, Welker White

Director: Kevin Smith

Rating: R