This article theorizes and charts the implementation of a learning activity designed from the hip-hop aesthetic of sampling. The purpose of this learning activity was to enable recent urban school graduates to reflect upon their previous schooling experiences as a platform for future learning in higher education. This article illustrates what these learning activities helped students learn from their urban schooling experiences, the epistemologies made available to students through sampling, and the concurrent barriers to learning that these activities also produced. These results contribute to the newest area of scholarship in hip-hop-based education with a focus on urban education.