As you may or may not know (or as you may or may not have figured out from reading some of my gloomier posts recently), I recently went through a breakup.  The evening of the final discussion, we were out to dinner, and when the topic came up, I insisted that we go somewhere more private to continue the conversation.  We went back to my apartment and as we sat down on the couch, I picked up my iPod.  "Let's see, what's good breakup music?"  At the time, I don't even remember what I put on -- something fairly quiet and innocuous, I suppose. 

Having the time to give it a bit more thought, I went through my iTunes library and here's what I came up with.  I made an iMix out of it for your listening pleasure, but so many of the songs weren't there that I wanted to include the entire playlist below.  It's in no particular order, and most of the songs are self-explanatory. 

I actually saw Jill Sobule last night at Joe's Pub (she was fabulous as always), and she pointed out that Angel/Asshole is a breakup song for the person who did the breaking up -- not your typical breakup song perspective.  Shoot me an email if you want a copy of the mix (assuming I can fit it all on one CD).