American Pimp (1999)

Street pimps, all of them African-American, discuss their lives and work: getting started, being flamboyant, pimping in various U.S. cities, bringing a woman into their group, taking a woman from another pimp, and the rules and regulations of pimping. The men are clear: it’s about money. The women work every night, hustle hard, turn over all their earnings, and steal anything they can from clients. We meet a few of the women, who tell us what they want from a pimp. We also listen to a women who’s legally employed at a Nevada brothel; we meet her White boss, a legal pimp. He and the street pimps, some of whom are now retired, make the case for legalizing the trade.

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Too $hort … Too $hort

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)

Clarence Sims … Himself (as Fillmore Slim)

Carol Speed … Lulu

Andre Taylor … Himself (as Gorgeous Dre)

Mel Taylor … Himself

Patrick Hegarty … Himself (uncredited)