Conor Oberst told the Independent newspaper July 18,2008 about the inspiration behind this song, which honors the life of a cancer patient. He explained: "I was walking to this liquor store and pharmacy in Nebraska with a friend of mine. Suddenly, she was like, 'Oh my God! Look at that old man sitting in that car, look at how small he is!' Of course, when we got closer we realized it was actually a little boy. It turned out he was waiting in line with his mom to get medicine, and we were there to buy vodka or something. My friend started crying, and we just went home. It was just one of those life experiences that begs to be written about. It's partly about Danny, but it's also about whether or not you can transmit your experience of love to another person and whether that message remains intact when it arrives."
"The Night Chicago Died" was written and recorded by the British group Paper Lace. They talk about Al Capone in the song, but got a lot of details wrong - understandable since they wrote it based on gangster movies.