In this article the authors provide a general overview of the controversies associated with urban street fiction, a brief introduction to the genre and an introduction to the complex representations of Black adolescent femininity within two contemporary titles, "Black and Ugly" (Styles, 2006) and "Bitch" (King, 2006). The authors provide a critical textual analysis that focuses on how women authors of urban street fiction rely upon and resist popular stereotypical representations of Black adolescent girls in their work. The authors argue that reading urban street fiction is a powerful out-of-school literacy practice that invites critical attention from educators.