One of the most significant traditions in Caribbean music is that of Calypso, which began on the twin island nation of Trinidad & Tobago. Calypso rhythms can be traced back to the seventeenth century when the first enslaved Africans were brought to Trinidad to work on the sugar plantations. The Africans were forbidden to speak to one another while they worked in the sugar fields, so they began to sing songs similar to those they knew in West Africa as a means of communicating and uniting with one another. This early Calypso music was developed from African call-and-response chants called "kaisos". These were songs of boastfulness and derision, often accompanied by the traditional African drums and chorus. Early Calypso music in Trinidad was sung in French patios, and was used as a covert way to ridicule the upper class and slaveholders.

The appeal of Calypso music broadened over the years and it became a tradition for Calypso singing competitions to be held annually, during the carnival season. Calypso's popularity soared after the abolition of slavery in the 1830s, and the music genre became synonymous with the Afro-Trinidadian struggle against colonialism. Calypsos typically involved ribald and sarcastic parodies about current events and social commentary, and because Calypso music garnered such widespread popularity and high regard, socially and politically conscious calypsos influenced many of Trinidad's most important social and political events.

Calypso made a breakthrough to pop music in 1954 when Harry Bellefonte recorded an album and "The Banana Boat Song (Day-O)" sold over a million copies. Soon after that, five million copies of the Andrews Sisters recording of "Rum and Coca Cola" were sold. Modern calypso music is now sung in English and African drums have been replaced by brass band and steel pan accompaniments. But Calypso is considered the heart of Trinidadian music and although it has become highly commercialized, this musical genre continues to shape the social consciousness of Trinidad.