Excluding Hip Hop culture and rap music from music education misses opportunities for addressing key aspects of popular culture, society, and students' lives. This article addresses intersections of Hip Hop, gender, and music education to forward potential Hip Hop praxis. After tracing related scholarship, I discuss and problematize representations of women in Hip Hop, including patriarchal, hetero-normative, and essentialized notions of Hip Hop that objectify and marginalize women. Through musicking, critical media literacy, and critical pedagogy young people might analyze and engage critically with Hip Hop and issues of identity, meaning making, representation, and agency in music education.