The Art of the Pimpossible

Created via word merging, the term pimpossible is a mashup defined, according to Chi-Town comedian DeRay Davis, as “anything above and beyond regular pimpin’.” It’s the core concept behind a kind of street-based supercapitalism designed to breed Benjamins by whatever means available, from hawking hubcaps to selling hos. And DeRay...

By S. Pajot

October 15, 2009

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Created via word merging, the term pimpossible is a mashup defined, according to Chi-Town comedian DeRay Davis, as “anything above and beyond regular pimpin’.” It’s the core concept behind a kind of street-based supercapitalism designed to breed Benjamins by whatever means available, from hawking hubcaps to selling hos. And DeRay has a doctorate in it. He’s hustled weed, rhymes, and threads, although joking remains his most marketable skill.

Originally mentored by fellow South Side natives Bishop Don Juan and funnyman Deon Cole, Davis is on the cusp of mega-pimpdom. Over the past few years, he has starred alongside Eddie Murphy and Cedric the Entertainer, guested on HBO’s Entourage, and created skits for Kanye West. He’s also been called “the funniest dude alive” by O.G. comedy king Katt Williams. So, this Saturday, witness the pimpossible when DeRay bum-rushes the Miami Improv for some freestyle funny stuff. Showtimes are 8:30 and 10:30 p.m. Tickets cost $18.19 plus the usual two-drink minimum.
Fri., Oct. 16, 8:30 p.m., 2009

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