The authors utilise the format of a dialogue in this essay to explore the place of hip-hop in the United States College classroom. Dialogue fosters a spirit of collaboration that generates more reflective responses and can spark new ideas that would be difficult to think of individually. Previous scholarship has also argued that hip-hop is itself inherently dialogic in that it constantly converses with the world at large. Thus, through dialogue, the authors debate pedagogy as it intersects with hip-hop culture. First, they discuss specific strategies for integrating hip-hop into the classroom, using examples from a range of previously taught classes. Second, they discuss some of the challenges they have faced in teaching with and about hip-hop, particularly as it pertains to the social locations of teachers and students. Finally, they explore whether hip-hop pedagogies are inherently critical, liberatory, or radical.