9. Nebraska - Bruce Springsteen
So...how exactly do we go from songs about death and Hell to one of rock and roll's most celebrated songwriters? I mean, The Boss certainly has some dark songs here and there, but how the hell is he managing to fit on a list like this? After Darkness on the Edge of Town though, you couldn't imagine Springsteen in a darker place on Nebraska.
Left without his E Street Band and just an acoustic guitar and harmonica for a majority of these songs, Nebraska is one of the most sobering listens that you'll ever hear from Springsteen, with the characters in these songs at the end of their rope. Whereas Born to Run felt like breaking out to find freedom somewhere else, this is what happens when that freedom doesn't come, like in the title track when a man is sentenced to death row or in My Father's House, where you see Springsteen seeking closure at his folks' place and finding a shell of what it once was.
Although most of these songs have a bit of a bitter streak, you can pretty much let the protagonist on Johnny 99 say it all for the record, as he answers to his crimes by bringing up his troubled past and how "it was more than all this that put that gun in my hand." Sometimes the greatest darkness isn't so much in the people we see. It's everything else going on around them.