What is Hundredaire Playboy?
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A person who lives like a millionaire playboy (I.E. has no job) but has hundreds or less in the bank.
"I heard Josh took his date to the sizzler on their date... and she paid."
"Yeah, that dude's a real HUNDREDAIRE PLAYBOY"
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Chris "Ludacris" Bridges, T.I. comes in a close 2nd, luda only beats him due to the infamous diss track by Young Buck entitled..
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the art of screwing up words.
Crikey! That little moster bit off my whole hram!..