Historically, across U.S. education systems, traditional teaching strategies and school curricular practices have been anchored in Western views and Eurocentric frameworks that position whiteness as the center of legitimate knowledge and, as a result, other knowledge as peripheral and insignificant. In this article, we offer practical considerations for educators and researchers who seek to disrupt systems of oppression through the implementation of hip-hop based education. As an extension of culturally relevant pedagogy, we contend that the critical implementation of hip-hop based education must include an interrogation of educator and researcher positionality as it relates to hip-hop culture.