Watch: Jay-Z Talks Tough With David Letterman

Rapper discusses Brooklyn upbringing with the late-night host

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Jay-Z's appearance on the Late Show With David Letterman Monday night was probably a bit more awkward than either the host or the guest had anticipated. While Jay's conversation with Dave could have just been two millionaires chatting, it ended up more like a tense debate between a resident of a tony New York suburb and someone from Brooklyn's hardscrabble Marcy Projects.

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In the first few minutes of the conversation, Letterman very gingerly tiptoes up to asking Jay about his past as a drug-dealer — which is extensively discussed in his new book, Decoded . Jay describes the environment in his community during the 1980s as one stricken by "Reaganomics" and "Iran-Contra" before Letterman finally utters the word "crack." Jay also describes his neighborhood as a pleasant one that would suddenly turn "super violent" — Dave blithely asks about the source of the violence, and Jay says, "Little guys with big guns," which bizarrely gets applause.

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The conversation stumbles along for several more minutes and finally wraps with Dave asking Jay whether his success has spoiled his street cred. Jay responds, "[Maybe] for guys who are not really from the street!"

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