This chapter traces the influence of paperback books on American literary subcultures after World War II. Cheap, handy, and accessible for most readers, the mass-market paperback format at once democratized the culture of letters and exploited stereotypes for profit. When it came to race relations, paperbacks’ capacity for disrepute collided with African Americans’ struggle for civil rights in a subgenre called “black sleaze.” In the 1940s and 1950s, books that tackled racial violence were repackaged with prurient covers that emphasized the taboo of interracial sex. This set the stage for the 1960s, when direct-to-paperback books bracketed social upheaval in the real world for sexual hedonism in fantasy. White readers’ problematic consumption of black sleaze was epitomized by the release of Iceberg Slim’s autobiographical novel Pimp in 1967 by the white-owned, tabloid-oriented Holloway House. However, after seeing the racial composition of its readership change in the 1970s, Holloway House sidelined sleaze for black pulp fiction formula stories by black authors for black readers. The switch may have appeared to vanquish sleaze, but elements of it remained embedded in this masculinist subgenre of books, which went on to inspire key figures in rap and hip-hop culture.