This article focuses on a hip-hop perspective of school, schooling, and school music. The study involves applications of ethnographic (including autoethnographic) techniques within the framework of a holistic multiple case study. One case is an adult amateur hip-hop musician named Terrence (pseudonym), and the other is myself (a traditionally trained American music educator and scholar). My history as a professional educator and scholar juxtaposed with Terrence's perspective as a high school dropout offers a valuable contrast of beliefs, values, and assumptions about school and education. Exploring Terrence's experiences and perceptions helps us to understand him as a musician and learner and also allows for a critical investigation of my own perspectives. Recognising my assumption-laden perspectives offers meaningful layers of nuance towards complicating the relationships between schools, those who school, and those who are schooled. Implications for teachers and researchers include expanding considerations of vernacular music in school settings and encouraging critical self-reflection.