So I've spent a couple days trying to nudge the question from the side, trying to consider songs that I think of as heartbreaky without sending myself into a downward spiral that could take weeks to recover from.
Today doesn't get a list, and it doesn't get a video. mdlbear posted that Jordin Kare has died.
I remember one filksong from my first year at BayCon - Leslie Fish's "Banned from Argo," sung in the back corner of a party room by four people sharing a copy of Westerfilk. The next year, I went looking. I remember one song from my second year - Jordin Kare singing "The Bride of Saint-Germain."
I wrote about this before. Bride of Saint-Germain has, as far as I know, never been recorded. It's certainly never been publicly released. And now, no matter how well the OTW does in its struggles to get fanworks accepted as fair use, no matter what kind of precedents vidders win from congress... he's never going to record even one of the fannish concert versions that sometimes make their way to Youtube.
I loved Jordin's music; I have both Fire in the Sky and Parody Violation and I can sing along with all of them, even if I don't quite know all the words. The song that breaks my heart is the one I'll never hear again.