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For educators who navigate the nexus of social justice and Hip Hop with an ethic of healing racial trauma, we are aware of Hip Hop’s capacity to be a source of healing(mis)education and to reproduce harm at the very same time. In this chapter, the author takes up a question central to the seminal album The Miseducation of Lauryn Hill (Hill et al., 1998): “how you gonna win when you ain’t right within?” Turning to the field of education, the author offers Hip Hop as a mechanism of racial healing and cultural responsiveness within a society that is not right within, and grapples with what it looks like for Hip Hop to “get right within” as it mirrors the deep misogyny, violence, and capitalism that make up the very fabric of America (Levy 2019).