As educators endeavor to engage an increasingly diverse student population, the curricular inclusion of elements of popular culture has been found to represent a particularly meaningful and successful approach. Research has consistently documented how utilizing issues of interest to students enhances affective links to the classroom and engenders stronger academic performance and critical thinking skills. However, the impact of teaching popular culture on educators themselves has been largely ignored, with this paper suggesting that these classroom experiences encourage a mode of reflective practice that heightens awareness of positionality and its impact on educational philosophy. Through an autoethnographic account of a recent course offering on hip-hop culture, the author explains how this pedagogical and epistemological standpoint not only benefits individual educators, but also has the potential to contribute to larger institutional transformation.