I've been indulging my masochism by reviewing this thread, and I'll indulge in a bit of sadism by adding to it. Some of my favorite sad songs have been mentioned several times ("No Man's Land", "The Dutchman", "Streets of London") but some are oddly missing. My nominations for the ten saddest songs of all time, in the not yet mentioned division, are ...

1) Molly, by Biff Rose
    (If you've never heard Biff Rose, this song deserves a listen.)
2) Angel Over Montgomery, by John Prine rec with Bonnie Raitt
    (Best version is the duet on the Steve Goodman benefit album.)
3) Freeborn Man of the Travelling People by Ewan MacColl
    (Is this actually a trad song 'discovered' by MacColl?)
4) Changes by Phil Ochs
5) Walking on a Wire, by Richard Thompson, sung by Linda Thompson
6) Brother Can Spare A Dime, Yip Harburg
    (You've got to hear him sing his own song to fully appreciate it)
7) Ashoken Farewell, Jay Ungar
    (You don't need words to make a song achingly sad.)
8) Rambling Man, by Hank Williams
    (Sung at an exquisitely painful slow tempo.)
9) Joe Hill, lyr Alfred Hayes, mus Earl Robinson
    (Not to mention Billy Bragg's reworking of it re Phil Ochs)
10) Lonesome Death of Hattie Carroll, by Bob Dylan
    (also Percy's Song by BD.)

I am now going to hunker down behind a conveniently located virtual stone wall, while the brickbats fly.

-- Etan Ben-Ami