This song sees Paul Simon tackling aging. He told Mojo magazine July 2011: "'Old' was a song about people starting to kid you that you're getting old before you actually are really old, but now I'm actually getting there."
You're The One was nominated for a Grammy Award for Album of the Year in 2001. As a result Simon became the first artist to be nominated in that category in five consecutive decades (1960s-2000s). Paul McCartney also joined that club in 2006 with his album Chaos and Creation in the Backyard.
"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.