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In this chapter, I investigate the emergence of the postcolonial era, nation, and space in Trinidad and Tobago through songs of independence, which, I argue, are both political events and ongoing, dynamic cultural processes. This contribution draws on calypso lyrics written and performed to commemorate Trinidad and Tobago gaining political independence from Britain in 1962. Through the narratives of the lyrics, I examine temporality, the construction of national identity, the deconstruction of colonial identity, and the geographic reach of independence as a postcolonial trigger. Analysing its cultural production and content, I show how calypso is a relevant but until now largely overlooked archive for studying postcolonialism and nationalism in the Caribbean region. Looking at calypsos which were commissioned for and themed on independence almost sixty years after this crucial event reveals overtures of freedom and future aspiration blending with undertones of collective redefinition and historical significance. This project is important because it makes use of a meaningful aspect of Trinbagonian national identity to question what this identity is built on and whether its foundation has changed throughout the era of postcolonial independence. Moreover, I demonstrate that the ‘postcolonial’ as a period, person, and geopolitical state does not exist passively nor isolated from the ‘colonial’ but is rather composed and (re)constructed with the verses and refrains of past, present, and future independence.