The Player’s Ball (sic) takes place a couple of times a year, and it’s where they pass out the coveted “Pimp of the Year Award”. This year’s winner was Evan Xpays. AFAIK, it’s completely legit and the pimps are real. The last one took place in Vegas on January 8th.
The Hughes Brothers (Menace II Society, et al) made a documentary which follows the big pimpin’ lifestyle and pays a visit to the 1999 Player’s Ball. Here’s a review: