By taking an introspective look into my beliefs, perceptions, and life experiences this study will use an autoethnographical approach to examine the researcher’s evolution from street life, to prison life, to academic life. This study will examine the urban life experiences of the author, tracing a forty-six year span of Black male urban life to examine the potential value of America’s Urban youth. Critical pedagogy will be used as the theoretical framework for this narrative. This research is important because it will explore how Urban and African-centered literature was pivotal in inspiring the researcher to move from a criminal mentality to one of resilience, self-determination, and community uplift.