Breaking up is almost always sad, but the really sad breakups stick in our memories forever. Who knows? Maybe you two will be able to work everything out together after all. But drama movie characters don't have the benefit/curse of a lifetime of running into each other at the grocery store, so they often break up for good. And yeah, it's sad - here are four of the saddest.


Rick (Humphrey Bogart) and Illsa (Ingrid Bergman) are in love. Unfortunately, she's married to a Victor Laszlo, who's a very important person in the Allied war effort against the Nazis. And even rough, cynical Bogie realizes that there are more important things in this world than two people who love each other staying together - but the fact that they want to be with each other just makes it sadder. It could be worse, though: Illsa loves her husband and Rick gets to be friends with Claude Rains.


Woody Allen is playing an unhappy comedy writer dating a 16-year-old girl (what do you mean, "autobiographical"? Get outta here), but he dumps her when after getting together with the alternately pretentious and adorable Diane Keaton. It's sad, the girl cries, you know how these things are. But the REALLY sad part is after Woody and Keaton break up, and Woody tries to stop his former child girlfriend from going away to London, but they both know it's too late. The sad smile Woody gives into the camera is probably the best acting he's ever done in his entire career, and it's the capper to one of the saddest movie breakups ever.

"Chungking Express"

Wong Kar-Wai's romantic masterpiece is about how nothing's permanent, not even love—our the devastation that comes after a breakup. In two discrete but connected stories, two lovesick cops cope with getting dumped in various whimsical and twee ways. The first guy buys a bunch of pineapple that's about to expire (it makes sense in the movie, we swear), while the second guy resorts to talking to his furniture. Whatever it takes, fellas.

"Eternal Sunshine of the Spotless Mind"

It's common in the event of a nasty breakup to want to erase all memory of the other person in the relationship. But what if that technology actually existed? The actual memory erasure process would be pretty painful, as all those happy memories you didn't think you wanted get disintegrated before your eyes. That's what happens in this movie between Jim Carrey and Kate Winslet. Luckily (or maybe not), the memory erasure allows them to get back together again, although that might be just lead to the entire thing starting over again. Love is tough.