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.
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.
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!”