This article reviews the history of scholarship on racial authenticity within studies of rap music and hip hop. The concept of authenticity currently enjoys a central place in sociological work on popular music, subcultures, and racial identity. As a music and cultural form that straddles all three of these fields, the debates surrounding authenticity within rap and hip hop are as contentious as any. Using the year 2000 as an arbitrary dividing line, this article presents the late 20th century foundations of research on authenticity and race within hip hop, then moves on to discuss more recent developments in the academic literature. Despite hip hop scholars’ increased emphases on discourses of space and place, and processes of culture and identity formation, the field continues to be framed through notions of essential blackness, and critical interrogations of white hip hop legitimacy. After providing an overview of the state of the field, it is argued that greater attention to language use among hip hop enthusiasts, and a particular emphasis on hip hoppers who fall outside the black–white racial binary will prove fruitful in reinvigorating these longstanding debates. Ethnographic studies of local underground hip hop scenes within the Unites States are recommended as a logical place to begin.