The most comforting thing in the world is curling up and watching a teen movie from the '90s that you used to love. That era feels simultaneously like it was ages ago and also yesterday, and there's something so perfectly familiar and nostalgic about it. The teen movies from the '90s were solid, with tons of great plots revolving around proms, popularity contests, graduations, makeovers, and critically important moments in adolescent life. And one thing that you may or may not be surprised to find, on a rewatch, is just how many times your favorite '90s teen movies broke your heart.
A real teen movie connoisseur knows that the best '90s movies truly had it all, as far as tone and emotion were concerned. They were all totally funny, but they weren't great films unless they also had a romantic element, and a dramatic turn, and an "oh my god" moment that broke your heart. Because teen life, especially in the '90s, was complicated, and the best movies were the ones that truly understood that. Whether that complication came from a romantic betrayal, a serious insult dropped by a supposed friend, or a tragic death, all the "my heart is breaking" moments in the list below were crucial to the '90s teen movie experience.