American Pimp is a 1999 documentary that examines the pimpsubculture 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 1970s 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, Fillmore 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 hold straight jobs or those who are now in jail.
A 2009 HBO drama based on American Pimp that planned to examine the world of prostitution in Oakland, California came under fire from then Oakland MayorRon Dellums and other city officials before filming had begun. The planned show, called Gentlemen of Leisure would have focused on a pimp in his 40s and his attempts to get out of the business. Dellums worried about the impact Gentlemen of Leisure would have had on Oakland's image. "It is the mayor's view that this project goes against our vision of Oakland as a 'model city' and does a disservice to residents and visitors alike," Dellums' Chief of Staff, David Chai, said. "While the mayor understands that there are certain benefits to having a major film project in our city, he is not willing to support this project at this time. The people of Oakland have come too far to have our city's name trampled upon in the name of entertainment."