Calypso is a popular Caribbean musical genre that originated in the island nation of Trinidad and Tobago. The genre was developed primarily by enslaved West Africans brought to the region via the transatlantic slave trade during the seventeenth and eighteenth centuries. Although West-African Kaiso music was a major influence, the genre has also been shaped by other African genres, and by Indian, British, French, and Spanish musical cultures. Emerging in the early twentieth century, Calypso became a tool of resistance by Afro-Caribbean working-class Trinbagonians. Calypso flourished in Trinidad due to a combination of factors—namely, the migration of Afro-Caribbean people from across the region in search of upward social mobility. These people sought to expose the injustices perpetrated by a foreign European and a domestic elite against labourers in industries such as petroleum extraction. The genre is heavily anti-colonial, anti-imperial, and anti-elitist, and it advocated for regional integration. Although this did not occur immediately, Calypsonians sought to establish unity across the region regardless of race, nationality, and class through their songwriting and performing. Today, Calypso remains a unifying force and an important part of Caribbean culture. Considering Calypso's history and purpose, as well as its ever-changing creators and audiences, this essay will demonstrate that the goal of regional integration is not possible without cultural sovereignty.