Well, when I was a little tyke, my mother could make me cry by singing "Oh, Susannah." Later, it was "The Moon Shines Tonight on Pretty Red Wing" (the tune more of us probably know as "Union Maid.") My father always said that "your bladder's too close to your eyeballs" thing. But a couple of newer songs that I feel are quite sad are "I Remember Loving You" which I think might be by U. Utah Phillips, and "Here's to You Rounders" - sung by Bok & Trickett - I don't have any railroad bums in my family as far as I know, but there's something about those two that touches me.