re: Who is the most RESPECTED rapper?

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Drake will be remembered in 2020 like chumbawumba is remembered today

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Chumbawumba was actually a deeply respected band that had an accidental hit, completely unlike the rest of their material. They were a deeply political anarchist collective, more concerned with activism than music. Hell, they did a split disc with Noam Chomsky.

They also showed up on Letterman with one of the members wearing a t-shirt that said "One Hit Wonder". They had no illusions about the pop music machinery.

As for most respected rapper, Dre and Jay-Z have moved on to their middle age period, in which they are the Rapper Emiritus. No one thinks their new stuff is vital, but there's sort of a career value there. But hot names come and go, but they don't have the same kind of enduring legacy. I'd say a guy like Talib Kweli is the most respected, but I think he'd rather have Drake's money. But the most popular guys are rarely remember the most fondly, in any genre.