The saddest songs for me are the ones where there could have been a different ending, and those about bad things happening to people where they have no say - "Death of Queen Jane," and "Victor Jara" (words by ???/tune, Arlo Guthrie). Alice mentioned "There Were Roses." The first time I heard it was from a quiet voiced singer in a loud bar. Everyone quieted down to hear him (a miracle) and I was blubbering by the time he finished. The saddest songs have some sort of happy element (sometimes just a memory of happiness) in them as well - like James Keelaghan's "Kiri's Piano," and someone mentioned Garnet Roger's "Row of Small Trees," Jon's suggestion "Maggie." It adds contrast and makes the sadness even more intense.

They're all songs where you feel what happens instead of just hear about it. I'm glad to see I'm not the only one furtively wiping away tears at the end of a song.