Culturally relevant pedagogy is a framework that conceptualizes the process of student learning as contingent upon educators' deep understanding of students' cultural backgrounds to co-construct knowledge and develop academic skills. Concurrently, there are a growing number of studies that explore hip-hop as a culturally relevant curriculum for urban youth of color. This work explores the potential and pitfalls of hip-hop as culturally relevant pedagogy by offering insights from two studies based in Chicago that incorporate hip-hop discourses and ideologies into curriculum and programing in and out of schools. Insights suggest that hip-hop can be a powerful tool to engage youth of color, but educators must first truly grasp students' realities, develop strong relationships with students, families, and communities, and be committed to social justice.