Bad Bunny references traditional Puerto Rican genres—bomba, plena, and música jíbara—on Debí Tirar Más Fotos, which many have described as his “most Puerto Rican album yet.” The use of barriles (bomba drums) and panderos (associated with plena), layered with reggaetón rhythms and salsa samples, grounds the album in local musical heritage. While this project marks a new level of commercial and critical success for Bad Bunny through its embrace of traditional sound markers, such fusions are not unprecedented. Throughout his career, Tego Calderón has incorporated elements of bomba and salsa into his rap compositions, particularly on El Abayarde. Building on Bruno and Victoria’s concept of “productive nostalgia” in Un Verano Sin Ti, this paper compares Debí Tirar Más Fotos and El Abayarde, focusing on their use of samples and sonic markers drawn from bomba, plena, and música jíbara. I argue that both albums engage with representations of Puerto Rican identity shaped by state institutions and grounded in ideals of racial democracy through mestizaje. Through his deployment of traditional genres, Bad Bunny often reinforces state-sponsored narratives of racial harmony, whereas Tego Calderón foregrounds Black sonic epistemologies that challenge these discourses. Using frameworks of productive nostalgia, acoustemology, and Black Sound Studies methodologies, this study examines how each artist mobilizes local sound to negotiate, contest, or reimagine hegemonic constructions of Puerto Rican identity in the archipelago and its diaspora.