The most soul destroying song I can think of.
http://www.youtube.com/watch#!v=kNgvN6E4HRI&feature=related
What I love is the comments on YouTube, praising what a touching and beautiful song it is. It's so utterly hopeless and depressing, yet delivered so matter-of-factly with it's bouncy little tune, I find it just turns into comedy. It's like the Wheeler Family on Night Court set to music.