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Monopoly and pimps first of all don't really go together, and they aren't unique to the 80's (like, at all).
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very clever and polished design. Monopoly is about getting rich, but it's innocent because it's a board game - the pimp represents tainted money, so he complicates that innocence. Good touch!
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The pimp's shoes are very platform 70's style! And he reminds me of a cross betwix Elton John & George Michael!! I like it though :)
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He kinda does look like the Macho Man now that you mention it. "Ohhh Yeaaaaa". Thanks for all of the comments you all!
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~Chuck