10. Casablanca

Quite possibly the best breakup movie, Casablanca is about a couple that breaks up not because they want to, but for the good of the nation! Humphrey Bogart’s Rick Blaine has a problem: His ex-girlfriend Illsa (married, natch) totally wants to get back with him. “This is a problem?” you might be asking. Yes, because her husband happens to be an important figure in the fight against the Axis powers. If his wife leaves him for some guy with a lisp who owns a bar in Africa, it would crush him. So Rick does the patriotic thing and tells Illsa that their happiness is less important than the fate of the free world. That’s the real reason your relationship didn’t last, right?

9. Detour

Film noir crime dramas make some of the best breakup movies, mostly because of their bleak pessimism. And Detour is one of the bleakest, most pessimistic films of the bunch. It also features one of the most fatal femme fatales in the entire genre, Vera (Ann Savage). She’ll make that awful girl you used to date seem like Kitty Forman. Also, it just so happens that this film has entered the public domain, which means you can watch it for free online.

8. Vertigo

This makes the list of best break-up movies because the film’s central relationship is doomed from the start (just like all your relationships). Private-Eye Jimmy Stewart falls in love with a girl he’s supposed to be following. She dies (bummer), and he goes into some kind of guilt coma. When he wakes up, he ends up falling in love with her look-a-like (what a coincidence). And you thought your relationships were screwed up.

7. The Dirty Dozen

Almost all Hollywood action movies have some kind of a romantic plotline…you know, for the ladies. But if you’re looking for a breakup movie, you’re probably not in the mood to watch Neo get it on with Trinity, or Billy Crystal fall in love with Meg Ryan. That’s where The Dirty Dozen comes in. The closest thing to a romantic relationship in the movie is when psycho Telly Savalas tries to rape a Nazi chick. And if that somehow reminds you of your last relationship, your name is probably Jesse James.

6. Butch Cassidy and The Sundance Kid

After a breakup, it’s advisable to spend some time with your buddies. So it makes sense that one of the best breakup movies is also one of the best buddy movies. You’ll laugh, you’ll…well, you’ll laugh. There’s nothing to cry about, man! The ending is vague. I’m sure they survived. I don’t care what Wikipedia says!

5. Taxi Driver

“Well,” you’ll say to yourself, “at least I’m not this guy.” Travis Bickle makes a great breakup protagonist because you’re probably better off than he is, no matter what the circumstances of your recent breakup were. And it provides some helpful hints for the next time you get a date, like “don’t take her to a porno theater.” A good rule of thumb is to wait at least three dates before trying that.

4. Annie Hall

Yeah, it’s a romantic comedy. But it’s also one of the best breakup movies because the main characters {SPOILER} don’t stay together in the end! {END SPOILER} And since Woody Allen is at the absolute top of his game here, you’re bound to come away with it feeling a little better about not just relationships, but people in general…at least until you remember he ended up leaving his longtime girlfriend to get with her adopted Asian daughter.

3. Halloween

In the world of slasher movies, sex equals death. That’s not the worst philosophy if you’ve just gone through a breakup. So for one of the best breakup movies, why not go with one of the first slashers? Just don’t get any ideas from Michael Myers. Or comedian Mike Myers, for that matter. The Love Guru can’t help you now.

2. Revenge

Breaking up can put you in a dark mood. So it makes sense that the best breakup movies would be dark, dark, dark. Tony Scott‘s “Revenge” is probably one of the darkest—a violent, brutal movie by any standard.

1. Kill Bill

When “The Bride” runs off with a new man, her boyfriend, AKA Bill, takes the news very poorly. By poorly, I mean he wipes out her entire wedding party and leaves her for dead in a coma. Years later, when she finally comes too, it’s her turn at settling the score. If nothing else, this movie will make you glad that your survived your breakup. That, along with the fact that it’s one of the most fun kung-fu homages to come out of Hollywood makes it prime best breakup movie material.

(Special Thanks to Jame Gumb)