This dissertation examines the various ways in which pop-cultural illustrations of the “bad nigger” figure beginning in the late 1960s helped to shape the kinds of defiant and oppositional practices that define the lives of black male youths today. I offer a brief history of the cultural and literary trope of the so-called “bad nigger.” I not only chart the cultural and political expressions of the “bad nigger” trope from the antebellum South to the industrial North, I also offer a critique of these accounts of defiant black male behavior that have dominated much of the intellectual discourse. Writing on the Streets: Urban Literature’s Black Male Hero does not pretend that the struggles of poor black inner-city life are somehow romantic or dramatic. What this dissertation does do, however, is offer popular black male cultural productions as a new critical site for engaging the cultural politics of economic power and racial oppression. Much of the scholarship on black male youth culture fails to engage popular texts that respond to black peoples’ negotiation of global issues. The works that do engage popular expressions and cultural productions often underestimate the importance violence, defiance, and opposition plays in the construction of a black male identity, not just for poor urban black male youths, but for men of color in general. Thus, this dissertation intends to magnify the need for more critical inquiry into popular cultural productions such as “street literature” and rap music, both of which contain poetic as well as practical elements of community uplift and self-empowerment and engage issues of cultural nihilism and self-destruction. This project’s focus on non-canonical texts follows bell hooks’ methodology and whose intellectual philosophy argues for “learning in relation to living regular life, of using everything we already know to know more. Merging critical thinking in everyday life with knowledge learned in books and through study has been the union of theory and practice that has informed my intellectual cultural work” (hooks 2). My hope, therefore, is that the readings I offer here will open the possibility for scholars and students of literature to consider more earnestly the importance of popular cultural productions in black communities. Furthermore, I write this dissertation in an effort to convince cultural and literary critics to concern themselves with the unique history and plight of poor urban black males confronting oppression and struggling in this criminal society.