This chapter explores the music, writings, and performance of reggaetón artist Tego Calderón, who is often credited with making reggaetón mainstream in Puerto Rico. Calderón is known for his politicized lyrics and his embrace of an Afro–Puerto Rican identity and aesthetic. The chapter shows how Calderón’s reputation as an artist who incorporates Afro–Puerto Rican folklore into his performance has made him a uniquely Puerto Rican artist in the eyes of even reggaetón’s staunchest detractors. At the same time, Calderón revises these same elements of Afro–Puerto Rican culture to articulate a serious critique of the disparagement of blackness that is part and parcel of dominant discourses of racial democracy. This chapter shows how Calderón draws from diasporic resources from throughout the Americas to express a black diasporic identity that refutes discourses of racial democracy in Puerto Rico.