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Sufjan Stevens – Chicago Lyrics 12 years ago
I think this has to do with a guy who keeps dropping everything to restart his life. He first tries to be optimistic and drive to Chicago. (I fell in love again. All things go, All things go. Drove to Chicago.) By saying he fell in love AGAIN, that must mean he "falls in love" and drops his life to move for a girl often. "All things go" means he dropped everything he had to move for her. He couldn't even afford it so he had to sell his clothes to the state. He sold everything and gave up his life for this new one. Eventually, he found out moving for her was a mistake and he shouldn't have dropped his life to restart it with this girl. Then, he ends up doing the same mistake over again. He wants to be optimistic and restart his life in New York. Him and his buddy take a van over to NY and he can't even afford it. He's so poor he has to sleep in parking lots. It's like history is repeating itself. He had to sell his clothes in order to afford living in Chicago and now he has to sleep in parking lots in order to live in New York. He then says "If I was crying, it was for freedom, from myself and from the land." This is to show how he now hates New York and wishes he never moved there. He then found out that was a mistake, too. So he keeps reiterating "I made a lot of mistakes. I made a lot of mistakes." because he realizes you shouldn't drop everything and everyone for wishful thinking. "You came to take us, to recreate us." - That is his inner self talking about how he wanting to recreate his life and in doing so, it was a huge mistake. He shouldn't have been seeking a new life somewhere else. He should have been trying to fix his current one.

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