Heartbreaker #8: A River For Him by Emmylou Harris, on Bluebird.
Ms. Harris is acutely capable of locating the heartbreak in other people's songs, and has constructed a handsome career from this art. But she penned this one herself, and it's as lonely a song as you could hope to find this side of Hank Williams (lyrics here).
A friend asked me if I mightn't choose her cover of Steve Earle's Goodbye, from Wrecking Ball. I'm among the legion of fans who think Wrecking Ball is just about as good as she and Daniel Lanois get, individually or as a duo. And Goodbye definitely gives me the shivers and puts me in a minor key. It just doesn't get the tears flowing. This is because it is so obviously a sentiment voiced by a recovering addict: Was I just off somewhere or maybe just too high / But I can't remember if we said goodbye. That's chilling and deeply depressing, and quite sad for the person it's addressed to, but it does not come across to me as a "sad" song per se, if you see what I mean. It's too calculated. A River For Him, on the other hand, is messy with recognition of what's been lost forever.
But speaking of Steve Earle... Heartbreaker #7