The ethnographic study that forms the basis of this article investigated the ways in which three Black males, Darrell (15), Reggie (15), and Dave (16), negotiated the messages of rap and the mass media to form their own counter-narratives of Blackness. The article aims to: (1) demonstrate how Black males are deconstructing rap to expose racial stereotyping within society and the media; (2) explore how Black males are debunking monolithic notions of Black masculinity; and (3) investigate youths’ knowledge-making processes outside the walls of their schools.