12. “A Guided Tour of Chicago” by The Lawrence Arms
Most Chicago line: “He's Darren in front of 7-11 on Walton and State. She's Babs up and down on Belmont right by the train. He's buddy and his wife in Uptown, by the Aragon, he's Andy selling Streetwise at the White Hen in Boystown. He was Ed from the South Side who gave me cigarettes and hope at Walgreen’s on Belden and Clark where inspiration dies alone.”
Few songs pack in more references to Chicago than this lightning-paced track from local punk goofballs The Lawrence Arms. Any song that references Uptown, the Aragon, Streetwise, and Boystown (along with specific 7-11, White Hen and Walgreen’s locations) automatically makes this list. That’s just the rules.