Ladson-Billings, Gay and among others have demonstrated the strong need for educational curriculum and practice to respond to the specific academic, cultural, and social needs of culturally unique, minoritized students. This article focuses on culturally responsive leadership practices for students with Hip-Hop identity performatives. This research uses theoretical frameworks from culturally relevant pedagogies and the scholarship that addresses how young students negotiate, perform, and reinvent and reestablish themselves through Hip-Hop culture, literacy, and identity. Such scholarship situates Hip-Hop pedagogies and student identity. This 2-year ethnographic study of an alternative school reports on how a culturally responsive school leader recognized and validated Hip-Hop student identities. Though he was somewhat removed from the Hip-Hop performative himself, the principal was able to create a safe space in which these student identities were able to exist, and in doing so, prevent the visceral impulse toward marginalization and exclusionary practice of Black and Latino Hip-Hop students that so many of his teachers possessed. Thus, the study discusses leadership theory, as it answers the following research question: How can urban school leaders play a role in forging a space for Hip-Hop identity development in the schools they lead? Secondarily it asks -- given the tensions and contestations in representations of Hip-Hop music -- if they should actually do this, and if so, what are the characteristics of such leadership?