Saddest: Hound Dog, Bay at the Moon" sung by Odetta. Saddest phrase in a song: "Aint nobody loves me but my mother, and I think she may be jivin' too" -BB King. The Irish sweep the catagory though, with Danny Boy, Parting Glass, Valley of Knockanoor and a thousand others. As G.K Chesterton says: "For the great Gaels of Ireland are the men that God made mad, for all their wars are merry, and all their songs are sad." Of course, Chesterton might have allowed as how the Brits had a little something to do with making Ireland sad.