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This line is said by an unnamed voice who is probably asking Jimmy literally where he is going. Jimmy responds by answering that he doesn’t figuratively know where he is going, as a stereotypical “smart” person might twist a simple question into something philosophical

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Follow up to School Spirit Skit 2 where the son of the character from that skit talks about his life. Just like much of The College Dropout, this is an obvious criticism of the higher education system in America.

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The elite can’t just pretend the lower classes are dumb, even as much as they try to Dumb It Down

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Macklemore’s stance on this subject would do a total 180 just five years later

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In track 10 off Macklemore’s 2005 album The Language of My World, Mack talks about his own mental conflict between whether or not to cheat on his girlfriend.

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The Seattle police completely focused on the poorer neighborhoods of the city, and almost totally ignored more well off areas like Macklemore’s

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The repeated use of come could be a subtle jab at the rap genre’s focus on sex over relationships, especially since Kweli’s raps on this song mostly focus on relationships.

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Macklemore’s in the bar, his girlfriend isn’t with him, and he really wants to get some action in before the night is up

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For a song to really mean something and live on, it’s got to have a message.

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