Stolen Car gets me every time. The original is a Bruce Springsteen tune. The Patty Griffin cover is even more depressing. You can find it on the Springsteen tribute album ("Light of Day").
Here's a snippet of it from a live Patty Griffin show:
http://www.youtube.com/watch?v=Aiqhz7TEB2E
Springsteen live:
http://www.youtube.com/watch?v=FPobte6iqSU&feature=related
If this song doesn't hit you hard, you either have no soul or you haven't hit your 30s yet.