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I agree with many of the recommendations on this thread, and I've discovered some new names I'll have to check out, but I don't understand why at least three luminaries have been left off:
DEL THA FUNKEE HOMOSAPIEN (also his group, Hieroglyphics)
PRINCE PAUL (and his group, Handsome Boy Modeling School)
and
PRINCESS SUPERSTAR (she ain't got a group, but she should!)
Del I've heard described as "the whitest black guy in rap," which makes no sense whatsoever to me. He's got some of the illest flow I've ever heard, and almost universally works in themes and ideas that make you think. The "Deltron 3030" album he did with Dan the Automator is, in my opinion, one of the most perfect hiphop albums imaginable. One track that I often cite to people goes:
I wanna create a virus
To bring dire straits to your environment
Crush the corporations with a mild touch
Crash your whole computer system and revert you to papyrus
I wanna create a super virus
Much worse than that old Y2K business
Cuz they don't want to unite us
So fuck it, total anarchy and can't nobody stop us
That's just SWEET.
Prince Paul, admittedly, I know less about, but he's well-revered as a producer, for one, and talks extensively in his lyrics about the politics of the hiphop industry and its effects on the culture it caters to. On his appropriately titled "The Politics of the Business" album, he takes the stale old skit track and turns it into a rap itself, including one that's a hokey radio ad for "double U double U double U Prince Paul dot com" in crescendoing falsettos and some disillusioned burnout cornering him on the street, admitting to buying into all the fads and wondering when it'll all pay off for him: "What do I gotta do to get in the GAME?!?"
Princess Superstar is definitely a pioneer in the genre, being a white female rapper who actually knows what she's doing rather than just reciting poetry over beats. Yet despite her talent, it doesn't seem anyone in the scene has deigned her worthy of being paid attention to: at this point, the rap community seems to have accepted a handful of white rappers, and to have accepted a handful of female rappers, but as yet they don't grant any cred to white female rappers. Which, if you actually listen to PS, has got to be one of the worst miscalculations they could do. Somehow, despite being a protoge of Kool Keith, she doesn't rate. I saw her open for N*E*R*D two years ago in Central Park, and she was actually BOOED throughout her set. And this was at a free show! Granted, the event wasn't well suited to her, but fuck, that takes some stones to heckle a show you didn't need to pay dick to see.
Sometime when I'm feeling more industrious I'll go into some more detail about the nerdcore rappers, but I think I gotta crash now.
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