17. Slowdive - Dagger
http://youtu.be/CczmMDvQDa0 This song is a little more open to interpretation than some of the others on this list. However, for sheer, numbing, melancholy alone this truly is a song that can be wallowed in with heartache. There are lot of overtones in this song aside from a breakup and heartache; drugs, death, love. 'I thought I heard you whisper/It happens all the time' is something anyone mourning over a lost relationship, or just simply mourning, can relate to; that lingering sensation of the one you love that almost becomes hallucinatory. Maybe it was your fault though 'You know I am your dagger/You know I am your wound.' 16. Eminem Kim (NSFW)
http://youtu.be/TNXYvidMaTM There are few artists who do breakup songs like Eminem. I mean, some may convey their dismay at the situation, their heartache, their pain, or perhaps sometimes their side in the situation they've found themselves. Eminem, he's more your kind of brutal murder fantasy breakup song through writer. As a prequel of sorts to '97 Bonnie & Clyde, we here go through the motions of kidnapping Kim, break between raps, rhymes and genuine anguished screamed and shouted vocals; running the gambit of vitriolic hatred, fear, and somewhere in there his own brand of love as he reminisces and cries how he love her in between brutal descriptions, and the undertaking of the final act itself.