The Hold Steady
Okay, this is going to be a section in itself. For good reason!
First of all, here's "You Can Make Him Like You," which is the title of my buddy Ben Tanzer's upcoming novel (which is awesome).
And then there's "Stuck Between Stations," which opens with a Kerouac reference ("there are nights when I think that Sal Paradise was right") and closes with the death of John Berryman ("she said you're pretty good with words, but words won't save your life and they didn't so he died").
And then there's "Cattle and the Creeping Things," which is mainly about junkies and the bible, and is part of what is essentially a novel in stories told as a rock and roll album, and was the only (to my knowledge) song that was ever annotated by NPR.