Singles — 1992
This movie is so '90s, you guys: it's set in Seattle during the grunge phenomenon and stars Bridget Fonda and Matt Dillon (with long hair!) as two Gen-Xers just trying to make it work, you know? The Cameron Crowe-directed rom-com also has cameos from some of the era's best bands, like Pearl Jam, Soundgarden, and Alice in Chains. Obviously the soundtrack is great, too.