Well, that’s pretty much what I thought would happen if I tried to dress like Madonna. Ever since I was little, I have been certain of two things. One, I definitely did see a ghost in my basement when I was five; and two, Madonna was the strongest, most unique, most uncompromising trailblazer pop music had ever seen, and deep down I always wished I were her. Madonna was fearless and unapologetic and in charge of both her naughty bits and yours. She gave a concrete visual to all my concepts of “cool,” and I always thought her traits—chief among them fearlessness—would magically become mine the second I slipped on fingerless gloves or a bedazzled cowboy hat. In October of 2001, I was invited to a costume party where everyone was “encouraged” to come dressed as a pimp. This was the beginning of the new millennium, a time when pimps had become a pop culture fascination again, but only to the point that they were considered wisecracking, colorful street characters and not dangerous Svengalis hell-bent on making a dirty buck.
