This chapter explores one of American popular music’s most polarizing moments in the late 20th century, the ideological and aesthetic divide between East and West Coast hip hop cultural practices. In both public press and recorded music of the era, a persistent dialectic emerged, one where East Coast authenticity was contrasted against West Coast artifice. This chapter explores how, by rooting the identity of artists to their location, whether urban or suburban, such gestures served to create a distinction in the growing market for rap music in the 1990s. In addition to examining these professed differences, the chapter investigates underappreciated similarities in the origins of East and West Coast hip hop practices stemming from Jamaican Sound System culture.