Most awesomely nasty and vicious break up songs ever.
I think that sits well enough on the specific/general spectrum to do a good top 5. Same rules as last post. Here goes nothing.
5. Song for the Dumped - Ben Folds Five. Funnily enough for a list in which stingingly smart insults are the norm, Ben Folds, lyrically clever nerd musician extraordinaire, hits a home run with words that possess no subtly or finesse whatsoever. "Give me my money back you bitch. And don't forget to give me back my black t-shirt." The intelligence was saved for the premise, and the punch is much in the piano as in what he's saying.
4. From a one nerd with glasses, a piano and plenty of rock, to another - indeed to the greatest of the all. Elvis Costello is of course the man to whom I refer (technically he plays more guitar himself - so sue me.) Here I've more picked an artist before having a specific song in mind, because Elvis has been doing bitter and brilliant better than nearly anyone for about 30 years. The winning song is Alison, but that may be because I'm too dumb to realise other songs I like more are also aimed at former partners. I mean we are talking Elvis Costello here. Still I'm very happy with this choice - the song is both understated and menacing at the same time.
3. In a repeat of 4, I insist Bob Dylan has to have a candidate on the list. The best choice is surely Like a Rolling Stone, which is one of the angriest and best rock songs of all time, as voted by music critics employed by Rolling Stone - who always seem to think white men perfected the genre in the late 60's / early 70's (in fairness they have a very strong case for both assertions.) The only problem is its technically only a common speculation that this is about an ex-girlfriend - Dylan could just have a serious grudge against someone he didn't sleep with; the song doesn't discuss the singer's relationship to its target. Let's stick with the it anyway though, because its just that good. A quote from a guy called Bill Wyman as read on Wikipedia says it better than I could:
"'Like a Rolling Stone' portrays an entire youth generation as a slumming sorority girl — and that's just the first verse. Then he gets nasty: The rest of the song is the rock 'n' roll equivalent of one of those scenes in The Sopranos in which a mobster systematically kicks the bejesus out of someone who's already down."
Yeah, that pretty much covers it.
2. You're So Vain, Carly Simon. I'm a sucker for a song with a punchline, especially one this good. It's not just the chorus that's great, either - "You're where you should be all the time, and when you're not your with some underworld spy, or the wife of a close friend." Ouch. Ouch ouch, even. This one had everyone asking "I wonder what poor jerk that was about." Several possible former flames of Carly get brought up. The best explanation I ever heard, on The Coulda Been Champions, maintained that different lines in the song were about different men, so that in effect this was about all of her shitty ex-boyfriends, and also about none of them. Which takes "you probably think this song is about you" to an entirely new level of absolute awesome. Way to screw with their heads, Ms. Simon.
1. Is, of course, You Oughta Know, Alanis Morriset. Absolutely in-fucking-credible. If I were her ex I would honestly have feared for my safety. "I wish nothing but the best for you both" shows Alanis sure knew how to use irony even if she didn't know what it was. Searing hatred drips from every line. Brutally intelligent and yet utterly irrational and passionate. "Are you thinking of me when you fuck her?" I bet he will now. Every time he's with a woman. For the rest of his natural life. Which she clearly hoped would be short - "But you're still alive!" ("and I wish that this was not the case, in case you didn't get that bit.") What a song. Lyrically, musically, and the incredible rawness of her delivery. It makes me flinch whenever I play it. Which is often.
Please don't hurt me, Alanis. I promise not to even try to go out with you let alone break up with you. I won't even ever come to Canada. Really.