So I still don't have "There Were Roses" (hint hint Mason, email it to me), but I found that I do have "Billy Grey" and "You'll Never Leave Harlan Alive". Besides, "There Were Roses" skates the fine line into activism songs. Don't worry, I'd still include it happily (or sadly, I guess), but I'm trying to talk myself out of including "Black Boys on Mopeds" which is totally an angry at the world issue song, but so damn spot on in sad-songness with the emotion in O'Connor's voice; and also Johnny Cash's "Ballad of Ira Hayes" which is also super issue-y and sung with more growling defiance than sadness and is sing-songy, but it is so damn sad and wretched that you can't really help having your heart broken. But if I include it, I feel like it is a small step to suddenly including "Bury My Heart At Wounded Knee" which is totally moving but all issue and completely not what I am going for with this time-wasting exercise.
I know that having mentioned Sinead O'connor that the obvious song for a sad mix is "Nothing Compares 2 U", but it was so popular and is so connected in my memory with images of the video that it takes a moment of active dissociation before I can just lose myself in the song, so it is out.
As long as we are talking issue-y but moving sad songs, "Tomorrow, Wendy" was a contender but is also out. The sound of the song is too pleasant and the voice too defiant. Of course this combination juxtaposed with the subject matter and lyrics is what makes it such a moving song, but still, out. I am tempted to let "Joey" in, though. Its melody might be a little too upbeat too, but damn that voice. Knife straight in the heart. If they hadn't backed her with pleasant upbeat tempos we'd have all killed ourselves or been scarred for life listening to Concrete Blonde. But the song is kind of a make up song, not the completely heart stomped tragedy we are going for here. If we were going to let "Joey" on board, then I feel like I'd have to also include "Jesse". "Jesse come home, there's a hole in the bed where we slept now it's growing cold," is about as pleading a line as you could ask for, but still it is a reconciliation song that only might be hopeless and besides, if I wanted my heart ripped out and stomped on by Joan Baez (which is exactly the kind of thing I am sucker for), I would include "Prison Trilogy", which I don't have and which brings us back full circle to issue songs.