What accounts for the persistence of the figure of the black criminal in popular culture created by African Americans? Unearthing the overlooked history of art that has often seemed at odds with the politics of civil rights and racial advancement, Under a Bad Sign explores the rationale behind this tradition of criminal self-representation from the Harlem Renaissance to contemporary gangsta culture. In this lively exploration, Jonathan Munby takes a uniquely broad view, laying bare the way the criminal appears within and moves among literary, musical, and visual arts. Munby traces the legacy of badness in Rudolph Fisher and Chester Himes’s detective fiction and in Claude McKay, Julian Mayfield, and Donald Goines’s urban experience writing. Ranging from Peetie Wheatstraw’s gangster blues to gangsta rap, he also examines criminals in popular songs. Turning to the screen, the underworld films of Oscar Micheaux and Ralph Cooper, the 1970s blaxploitation cycle, and the 1990s hood movie come under his microscope as well. Ultimately, Munby concludes that this tradition has been a misunderstood aspect of African American civic life and that, rather than undermining black culture, it forms a rich and enduring response to being outcast in America.