We study the role of Hip-Hop teaching artists in a school change initiative. A school-university-community partnership in a Canadian city, the project sought to develop a school-wide focus on the "urban arts" for student learning and wellbeing. The experiences of nine teaching artists over four years, examined through the lens of Critical Hip-Hop Pedagogy, offer insight into the roles of Hip-Hop based teaching artists in a nontraditional, arts-based, school change initiative.