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In this paper, I center my analysis of Puerto Rican destierro (Figueroa-Vásquez 2020) via popular music, starting with “Lamento Borincano” (1929) and ending with “LO QUE LE PASO A HAWAII” (2024). Labeled the first Latin American song of protest (González 1985), I argue how “Lamento” captures the painful lamentations of forced migration and uprootal at the hands of empire, and how popular musical genres like salsa and reguetón, continue to bring Puerto Ricans together to grieve. By reading these sonic contributions through the lens of lamentation, I argue how popular culture, in this case music, exposes the insidious nature of empire, and how music serves as a form of collective resistance. In this way, Puerto Ricans, via their own lamentations, come together and rebelled against colonial empire, as we see how Puerto Ricans organize to resist and disobey U.S. and Spanish colonialism. I conclude with thoughts on the continued work lamentation, collectivity, and rebellion.