In the face of systemic neglect of low-income urban neighborhoods, Hip Hop was much more than entertainment: it was a countercultural revolution embodied as a way of life bound to community action and social change. Hip Hop represents resilience, resistance, and redemption for those living on the margins; to this day, it is an art form for the underdog and is used in social action and political protest all over the world. Given their drastically different cultural underpinnings, it might seem counterintuitive to merge Hip Hop and therapy. In both, however, people are partaking in expressive practices to help them release, communicate, and connect. This article discusses the author's use of Hip Hop therapy (HHT) in a Bronx transfer school.