This is still one of my favorite sad ones. I'll whip it out when I feel like being mopey and dramatic. It was released in 1988 so more people should have had the opportunity to discover her. I don't think that they have, so it feels all the more personal to me when she says "take my life, I'll give you mine, you give me something to cry about". I adore this song.
Mary Margaret O'Hara – "To Cry About"