This chapter details the emergence of underground, the precursor to reggaetón, as a cultural practice of diaspora. It begins with a discussion of U.S. hip-hop, Jamaican dancehall, and Panamanian reggae en español that were key influences in underground’s sound and diasporic and racial politics. The chapter also provides important background about the Mano Dura contra el Crimen campaign in the mid-1990s in Puerto Rico, demonstrating how Mano Dura cemented stereotypes of urban blackness on the island that underground artists contested. A close analysis of Eddie Dee’s lyrics and music video for “Señor Oficial” exemplifies how underground artists drew upon diasporic resources to contest persistent racism within Puerto Rico’s so-called racial democracy. Finally, the chapter details the debates that ensued after an unsuccessful attempt to censor underground in order to demonstrate how the music’s racial politics troubled the hegemony of discourses of racial democracy on the island.