6. Big Eden (2000)
Henry Hart returns to Big Eden and winds up confronting his unrequited passion for his high school best friend and his feelings about being gay.
This movie, more than any other on this list, nails the feel of an old-school, turn-of-the-millennium romcom. At first glance, you’d think this movie about a successful New York artist returning to his small town would see him battling homophobia, but Big Eden depicts a kind of post-everything utopia that could only exist in the ‘90s. Nearly everyone in this rural town is not only accepting of the gay triangle brewing in their midst, but actively invested in it. As in any classic romcom, the outcome of this love triangle is clear from the start, but each relationship is as exquisitely detailed as it would be in a Nora Ephron film.
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