Jíbaro music, the country music of Puerto Rico, draws its lineage back to the ancient décima from Spain, featured in music and poetry all across Latin America. The Commonwealth of Puerto Rico adopted this genre as reflecting authenticity and values. Yet its policies forced nearly all of the music’s exponents to seek an audience in a diaspora that revered them as the purveyors of the lost homeland. New York City became an important hub of this genre; arguably, it saved it from extinction. The scant scholarly literature on jíbaro music has unreflectively echoed the construction of jíbaro as traditional, Hispanophile, and presumptively white music. Through the figure of Ernestina Reyes, “La Calandria,” in the context of her larger cohort of great country music singers, this chapter offers a completely new interpretation of this genre and questions the empty space it assigns the woman singer, who is invariably spoken about as always already inferior to all male singers. The chapter comments on the contrast between working-class musical aesthetics and practices and the overwhelmingly bourgeois sense of taste that has ruled accounts of pop music.