10. Pootie Tang (Lance Crouther); The Chris Rock Show
Do we really need to explain why this guy easily cracks the top ten? He's a nightclub performer, he has more ladies than you, and if you step to him, he'll put you down...with his belt. Not to mention Louis C.K. wrote and directed the so-bad-it's-good film based on Pootie's appearances in Chris's sketches. The ultimate pimp.