This chapter develops a working framework, always open to revision, as time, change, and history mandates, a provisional understanding in how black males in hip-hop become black in and through the cultural intersections between media, race, language, culture, fluidly defined. It examines how media frames blackness in relation to the discursive and material processes of identity formation in response to its gaze in black popular culture. Interrogating racial formations of black masculinity within and between these discourses is indispensable to deconstructing the media war on black male youth. The chapter discusses the contradictory relationship between urban youth culture, media, and urban education. It serves as a guidepost for how to deconstruct to reconstruct more positive and empowering identities for black male youth. Media is often the first point of reference, regarding whites' interpretations of the urban "black experience" for a majority of white female educators, teaching in urban schools.