One of my favorite Elliott Smith songs is Pitseleh, which means "little one" in Yiddish. It's so filled with anguish, despair and even self-loathing. He knew he had this great thing, this relationship, except it was doomed because he's so flawed. So he tried, but it just didn't work out. And as he realizes it'll never work, he ends with the line, "I never meant to hurt you", and shuffles away underneath grey skies. Being a seasoned veteran of a million fucked up relationships, my heart just breaks when he sings "The first time I saw you/I knew it would never last/I'm not half what I wish I was." I guess it's not necessarily a good thing to be able to relate to his songs, but there is beauty in this sorrow.
Elliott Smith > Pitseleh