The Top 10 Best Breakup Movies

5. Celeste & Jessie Forever

Not every breakup is messy. Sometimes people can be adults about it. Take Celeste & Jessie Forever. Two high school sweethearts (Rashida Jones and Jesse Samberg) marry young and seem to have everything going for them… Until they don’t. Things just aren’t the same anymore and Celeste thinks they should separate. The two manage to be surprisingly grown-up about the whole thing, even going so far as to infuriating their friends with how they’re still such good friends. That changes when they actually do start to move on. As they date other people, doubt fills their minds and they wonder if they did the right thing. I don’t want to spoil it for you, but it wouldn’t be on this list of breakup movies if they got back together. They do make it work in the end, which makes this a different kind of feel-good story.

4. Blue Valentine

From a feel-good story to a brutal one. Blue Valentine is a brilliant film, but it’s also really hard to watch. That’s probably because Ryan Gosling and Michelle Williams are so damn good in it. Their romance is a whirlwind affair complete with an embarrassing musical number in which Gosling plays a ukelele (it was the endearing and quirky thing to do in 2010). An unexpected pregnancy puts a stop to that and the two marry in an attempt to “make it work.” Well, marriages made to solve problems don’t have the best chances at working in the long run. Cut to 5 years later and the two can’t stand each other. No matter how hard they keep trying to “make it work” they just aren’t meant to be. People change in relationships and not always for the better, so not every breakup is a bad thing.   

3. The Way We Were

The Way We Were is a sorrowful cautionary tale about dating the idea of someone rather than the person themselves. The film stars Barbra Streisand and Robert Redford as a couple from different worlds that fall madly in love with one another. That is until they get to know each other. For Redford, he found himself fascinated with a woman who was unlike anything he’d met in the elitist world he grew up in and thought different meant better. For Streisand, she met a man who she imagined had unlimited potential and squandered it by compromising (aka being a realist). Their love was very real when they first met, but over time it soon became a question of loving the person or the idea of the person. The film teaches a lesson many of us have to learn the hard way.

2. Eternal Sunshine of the Spotless Mind

After a breakup, it’s easy to want to forget everything that happened. That’s why Michel Gondry’s surreal film Eternal Sunshine of the Spotless mind ranks so high on this list of breakup movies. They call it a “breakup” because it quite often breaks your heart and that can be pretty traumatic, especially if things get messy. For the two lovebirds in the film (Jim Carrey and Kate Winslet) all they want to do is forget everything about each other. Fortunately, there’s a way to do that. A medical process that erases select memories. Sound great? Well, the thing is that if you don’t learn from history you’re doomed to repeat it. It’s hard to know what red flags to keep an eye out for if you don’t remember what any of them look like. The film teaches that sometimes the painful memories are the ones you need to hold onto the most so you don’t hurt yourself again.

1. 500 Days of Summer

When it comes to breakup movies, few hit the nail on the head quite as hard as 500 Days of Summer. In it, a guy named Tom (Joseph Gordon-Lovitt) falls for the dreaded manic-pixie dream girl trope (Zooey Deschanel). Everything seems great at first because she’s so different from other girls and such a free spirit. The two are perfect and quirky together. The thing about the “manic” part of a pixie dream girl is that mania never lasts. While Lovitt falls head over heels for her, she maintains her emotional distance from him in a toxic display of independence. The end result is a guy who thought a girl loved him when she never “believed” in love in the first place. Tom is a hot mess when he’s dumped by Summer and it’s a harrowing journey as he tries to put himself better. Kintsugi shows us that sometimes the repaired version is even better than the original.

Honorable Mention: Casablanca 

I was tempted to include Casablanca in the top 10, but after thinking on it I realized that it was more about accepting the way things are rather than living with the dreams of what could have been. It’s still technically a movie with a pretty severe breakup in it, but in the end, Rick has to get over his resentful feelings in order to save the woman he loves.

Those are my picks for the top 10 breakup movies of all time. There are plenty more out there and I’d love to hear what some of your favorites are in the comments below. As always, I’ll be updating this list as new and improved breakup movies hit theaters. So, be sure to check back from time to time to see how the rankings might have changed.