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The 50 Best Radio Freestyles

21. Super Natural "Words" (1993-94)

Station: WKCR (89.9FM)
DJ: Stretch & Bobbito
Best Punchline: "Brains expand when I gets busy on the flex/Who's next?"


Supernatural is widely regarded as one of the greatest freestyle rappers of all time. Although, he never found mainstream success (read: sold albums), he's maintained a successful career on the performance circuit and remains a staple at festivals such as Rock The Bells.

Supernat's claim to fame is taking words or items people toss him during his freestyles, seamlessly incorporating them in his rhymes in real time. On Stretch & Bobbito's show, he flaunted this ability by flawlessly integrating such random and bizarre words as: “tasty cupcakes,” “yellow teeth,” “skinny bones,” “Haitian women” and “receding hairlines,” into a dazzling five-minute freestyle.

Being able to rhyme words that make no sense is fairly easy to do, but making coherent raps out of them is a whole other matter, and nobody does that better than Supernat.

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