11 Times '90s Teen Movies Broke Your Heart

by Kayleigh Hughes
20th Century Fox

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.


When Kat Reads Her Poem About Patrick In '10 Things I Hate About You'

Even after Joey ruins everything in an equally heartbreaking scene, Kat (Julia Stiles) forgives Patrick (a swoon-worthy Heath Ledger) and bares her soul in front of the class. Every strong but vulnerable young girl could relate.


The Devastating, Iconic "Am I A Bet?" Moment In 'She's All That'

When Laney Bogg's heart breaks, all our hearts break. She didn't deserve to be treated as a plaything for the awful popular kids.


When Amanda Mistakes Preston For A Jerk And Humiliates Him In Front Of Everyone In 'Can't Hardly Wait'

Poor Ethan Embry, whose sweet, lovestruck character Preston is the only one who sees Amanda for the incredible person she is. His poor puppy dog face falls and your heart breaks.


When A Young Josie Geller Gets Egged On Prom In 'Never Been Kissed'

Like 60 percent of Never Been Kissed is just heartbreaking scenes of Drew Barrymore's sweet nerd character being treated terribly, but nothing punches you in the feels quite like the devastation of seeing her glowing with excitement about going to prom, only to be egged by her date as a cruel prank. I want to give her a million, billion hugs.


When Romeo Thinks Juliet Is Dead In 'Romeo + Juliet'

You know it's coming, and it still completely breaks your heart every time. Leonardo DiCaprio's tears over Claire Danes' Juliet are enough to make you want to give up. (Mercutio's death is also definitely a runner-up.)


When Meagan Has To Leave Graham At Camp In 'But I'm A Cheerleader'

Homophobic forces kept them apart, but Natasha Lyonne's Meagan comes back, saves Graham, and wins her heart in an amazing cheer sequence that is so sweet it breaks your heart and heals it back up all at once.


When Kim And Edward Both Recognize They Can Never Be Together In 'Edward Scissorhands'

Jonny Depp's poor Edward has just saved Winona Ryder's life, but they both know they'll have to be separated forever. He's too good and pure for that town, and it's tragic.


When Chase Hooks Up With His Ex Dulcie And Betrays Nicole In 'Drive Me Crazy'

Adrian Grenier's Chase and Melissa Joan Hart's Nicole are clearly meant for each other, but they have a huge fight that leaves Nicole tearful and hurt, right before prom. It sucks to watch, but the two crazy kids eventually get it together.


When Cher Gets Called A Virgin Who Can't Drive In 'Clueless'

Wow, Tai. Way harsh. This awful friend breakup is a huge emotional blow that sends Cher's life spiraling.


When Roberta Learns The Truth About How Her Mom Died In 'Now And Then'

It's heart wrenching moment, and it's a good thing she has a group of best friends who are there for her when things get hard.


When Sebastian (Spoiler Alert) Freaking DIED To Save Annette In 'Cruel Intentions'

Why did sultry bad boy Sebastian (Ryan Phillipe) have to die? He had finally learned to love, thanks to Reese Witherspoon's brilliant, clever Annette. It's all Kathryn Merteuil's fault.

Honestly, this list makes it clear that it wasn't a true '90s teen movie unless there was some serious heartbreaking moments.