melancholy songs

I'm not usually drawn to melancholy songs, but every once in a while I'll lock onto one and listen to it to death.  When I was in high school it was Elle G. by The Newsboys.



In my twenties I could not stop listening to the Johnny Cash cover of Hurt.



Oddly enough, the melancholy song I've been going to lately is an old one rather than a new one.  It's the Gary Jules cover of Mad World.


For whatever reason, these particular songs are the sad ones I decided I wanted to listen to when I want to listen to a sad song.  The songs themselves feel like they have more substance than a run-of-the-mill sad song, but that might be me rationalizing after I've decided I like a song.

Do you have any that serve this same function?