My recent Johhny Cash post had me thinking about song categories again...quite a few songs have a psychopathic character or event about a guy or gal that does something really despicable - with no apparent remorse. I'll start off with the Johnny Cash song I mentioned:

Cocaine Blues - but the author is T. J. "Red" Arnall - whose version is a lot more matter-of-fact hillbilly bluegrass - Johnny Cash sounds like a 'baddder' due to me

On the Banks of the Ohio - another guy that is hard to relate to

Nebraska - Bruce Springsteen's character in this song sounds like a guy that deserves no pity either

Who can outdo me for songs about even more despicable characters ? : ) More points if it's your own original !!! :0