saddest song....hmm.. a tough one but " The Hobboes lullaby" by Woody guthrie (?) sung by Emmy Lou Harris is up there The Band played Waltzin' Matilda is a great Anti War song Fire and rain , James Taylor but as a boy a record called " A little dog cried" always set me howling with tears. My brother would put the record on the player and see who would cry first!