Hip hop music and culture have a complex identity in that hip hop is based in self-determination, resistance, and the long enduring fight for Black freedom, but was also created alongside the seductiveness of the material and psychological conditions of capitalism, sexism, and patriarchy. Hip hop pedagogy (HHP) as a pedagogical framework is birthed out of that intricate balance in hip hop. Given those basic contradictions, I explore the complex personhood of hip hop and its relationship to HHP, which generates humanizing, critical, and creative pedagogical (re)interventions and sensibilities that foster self-determination, self-knowledge, and acts of resistance with young people. I do this by examining hip hop educational spaces that nurture the ways of doing and knowing youth who are deeply informed by hip hop.