In reflecting back on the halcyon days of '90s teen movies, it may be easy to just think about the screwball comedies or the intense romantic dramas. But what about the films that fell somewhere in between, that mixed happiness and sadness or love and anger, all culminating in some truly heartbreaking moments? When it came to articulating heartbreak, '90s teen movies somehow managed to nail it on multiple occasions.
Experiencing heartbreak in real life can feel like a huge swell of emotions. Depending on the situation, the moments right before heartbreak can feel intense. You somehow manage to feel everything all at once — either joy, sadness, anger, and so forth — until that turns into something like heartbreak. That cycle of emotions getting amplified on the big screen in a '90s teen movie (which already has the potential to be a hormonal affair) only makes the heartbreak you're watching all the more intense.
In this realm of heartbreaking '90s movies, there's a handful of contenders that are quantifiably heartbreaking but they discuss that heartbreak in a variety of ways. Some heartbreaking plot developments or twists are downright sad and others will probably make you feel happy once the heartbreak dies down. Prepare yourself: It's about to get all kinds of emotional in here.
1. Romeo + Juliet
This updated Shakespeare play is the epitome of heartbreak. What's worse than falling in love as a teenager and being kept apart by your parent? Please don't resort to what Romeo and Juliet do in real life in order to deal with heartache, though.
2. Empire Records
Underneath its funny exterior, there's some serious sadness brewing in Empire Records. Whether its the realization of a dream deferred because Lucas stole Max's money and went on a gambling spree or the revelation that Debra has attempted suicide, leading the staff to hold a mock funeral for her, things get bleak. Not even the celebration of Rex Manning Day could keep your heart from breaking.
3. Now And Then
There is a bittersweet kind of heartbreak happening in Now and Then. Sure, these four best friends reunite years later. And yeah, when they're younger they remain quite close. The heartbreak happening here is closely related to the growing pains of being a young teen: whether it was Samantha and her family go through a divorce or Roberta experiencing her first crush gone awry, Now and Then understood the pain of being a teenager.
4. Cruel Intentions
Cruel Intentions was a sexy-as-hell teen movie, to be sure, but there was some seriously heartbreaking stuff happening. Not only was Sebastian's untimely death at the end the ultimate heartbreak, but the ways in which he and his step-sister Catherine toyed with their peers' hearts was just too much.
5. Never Been Kissed
On a scale of nine to 10, how badly did your heart break when Never Been Kissed flashed back to Josie's horrible '80s prom night? I know, I know: She finally got her kiss and a happy ending, but still, this was so sad.
Pleasantville got very real, very quickly. What began as a film poking fun as squeaky-clean '50s sitcoms became a timely and beautiful commentary on topics like individuality, sexuality, and racism. Moments like the soda shop getting destroyed for a provocative window display or Betty almost getting sexually assaulted by a group of teenage boys really turned up the heartbreak dial.
7. The Virgin Suicides
Poetic, melancholy, and sad: it's easy to write off The Virgin Suicides as a dreamy book-to-film adaptation but this film is heartbreak incarnate. Behind the hazy, nice memories of the Lisbon sisters lies a mystery wrapped in nothing but pain. Why did the sisters kill themselves? As the neighborhood boys attempt to pinpoint why their deaths by suicide happened, it becomes clear there was something very serious and sad happening to them all.
8. Welcome To The Dollhouse
As a '90s teen, it doesn't get much bleaker than being Dawn Wiener in Welcome to the Dollhouse. A darkly comic coming of age, Dawn can't catch a break from her peers, crush, or family. Her problems are painful and all too real, like how she's ignored by her parents and physically threatened by a male classmate.
9. Before Sunrise
Another bittersweet and beautiful heartbreaking film, Before Sunrise is a beautiful thing to watch. Knowing that Jesse and Céline, who meet on a train to Vienna and decide to walk around the city together, won't end up together despite their blatant attraction is so heartbreaking.
Casper is definitely a friendly ghost, somehow keeping the mood light as he bonds with human bestie Kat, despite the heartbreaking fact that he is a dead child. How Casper manages to not succumb to the bleakness of the afterlife despite having to share a house with his terrible uncles, who are also ghosts, is nice but still incredibly sad.
Titanic is the ultimate in heartbreaking '90s movies. Watching Rose and Jack fall in love, only for Jack to die in the end, was the worst kind of heartbreak to experience.
Welp, this whole list just broke my entire heart all over again. Time for me to get some tissues and try to self-soothe.