In this article, the social imagination of community-based sites of urban resistance enable out-of-school literacy practices in Black popular culture to foreground the contemporary context in which youth empowerment is nurtured in out-of-school learning settings. Second, the author chronicles how youth advocates in hip-hop--based community settings organize culturally relevant life lessons to political empower and facilitate healing of youth. Finally, the author expands insights from his previous work as a youth advocate for local high school rap artists in at-risk conditions of an urban community. As participants at a youth center, the students learned how to use the art of emceeing as a cultural outlet to overcome and heal from difficult life struggles. The students also developed strong mentoring relationships with youth advocates at the center. Finally, the author worked with the center in designing critical hip-hop curriculum texts to challenge gang activity, incarceration, and death. Each of these events demonstrates the cultivation of community-based literacy practices in hip-hop as social justice education.