Using a pilot program in one Chicago elementary school as a case study, this article reports findings of an ethnographic investigation on the impact of Hiphop based music education at the elementary school level. The findings describe how this program facilitated a process by which the youth participants were empowered through (a) identity building within a community of practice, (b) musical expression as internal critical dialogue and an external critical voice and, (c) a classroom ethos supportive of expression related to contemporary Black youth subjectivity. The findings of this study suggest that implementation of Rap music making as an in-school activity involves creative use of computer and multimedia technologies to develop novel social skills and competencies in elementary school youth and thus, also provides a framework for better promoting learning equity (race, ethnicity and class) with digital media and cultural responsiveness in urban education.