1999 documentary that examines the pimp subculture in the United States. It was directed by the Hughes Brothers, the filmmakers behind Menace II Society and Dead Presidents.
The documentary consists of first person interviews of people involved in the pimping lifestyle. The interviews are separated by short clips from 1970's blaxploitation films such as Willie Dynamite, The Mack, and Dolemite.
The first portion of the documentary focuses on pimps working illegally. The illegal pimps that are interviewed are from all over the United States, e.g., Charm from Hawaii, Filmore Slim from San Francisco, and Payroll from Las Vegas. These pimps, and many others discuss their theories on the history of prostitution. The pimps go on to talk about their philosophy on pimping, and how they live their daily life.
The film also discusses the legal sector of prostitution. Dennis Hof, the owner of the Bunny Ranch in Nevada, is interviewed. He feels that Nevada is much smarter than the other states because they have imposed the proper health and background checks on prostitution, instead of trying to suppress prostitution by making it illegal.
The majority of the documentary glorifies the pimping lifestyle. The pimps and prostitutes interviewed mainly discuss the perks of the lifestyle. They talk about the money they have made, and the expensive suits and cars they were able to buy; however, near the end of the film, the interviews involve prostitutes that have died from the lifestyle as well as pimps who have retired and lead straight jobs or those who are now in jail.
John S. Dickson ... Himself (as Rosebudd)
Antonio Fargas ... Link Brown
Heidi Fleiss ... Herself (archive footage)
L. Hammond ... Payroll The Pimp
Hugh M. Hefner ... Himself (archive footage)
Dennis Hof ... Himself
The Bishop Don Magic Juan ... Himself
Max Julien ... Himself / Goldie
Rudy Ray Moore ... Dolemite
Conan O'Brien ... Himself (archive footage)
Roscoe Orman ... Willie Dynamite
Kenny Redd ... Himself (as K-Red)
Todd Anthony Shaw ... Too $hort
Clarence Sims ... Himself (as Fillmore Slim)
Carol Speed ... Lulu
Andre Taylor ... Himself (as Gorgeous Dre)
Mel Taylor ... Himself