Mellencamp was working on his Cuttin' Heads album when his best friend, Billboard editor Tim White, died suddenly. "It took all the wind out of my sails," he recalled. "This song was written after Tim's death. I was pretty unhappy, and I was trying to make myself feel better."
"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.