Their second film was Dead Presidents in 1995. Dealing with the black underclass society like their feature film debut, and also starring Larenz Tate, the film centered on war veterans during the racially charged Vietnam War era. The film, which was released at the New York Critics Film Festival, failed to make as much of a profit as their first film. They followed Dead Presidents with American Pimp, a feature-length documentary about the underground pimp culture and exploitation of women. It premiered at the 1999 Sundance Film Festival. They had originally set out to do an adaptation of Iceberg Slim's novel Pimp, but someone else acquired the rights. The brothers have stated that the film's perspective was partially shaped by being raised by their mother, who is a feminist. In between projects, they filmed several anti-handgun public Service announcements.

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