Hip-hop-based education (HHBE) research analyzes how hip-hop culture is used to produce favorable educational outcomes. Despite its richness, the work reveals little about how to prepare practicing K-12 teachers to use HHBE toward the critical ends reflected in extant HHBE literature. In this article, we challenge many tacit assumptions of HHBE research by examining the curricular and pedagogical wants and needs of in-service teachers who are interested in HHBE but who are not familiar with hip-hop's unique history and culture. Through a collaborative self-study with a teacher-educator, we, as Black male hip-hop insiders, reflect on the promises and pitfalls of preparing predominantly White teachers to incorporate hip-hop into their teaching and learning repertoire.