Although Calypso was internationally popularized by artists of various backgrounds, like Jamaican American singer Harry Belefonte, ask anyone who knows and they’ll tell you: if you’re not a Trinidadian, then you’re not a Calypsonian. A genre which owes its colorful humor to Trinidad’s irreverent and easy-going national character, Calypso has produced some of Western world’s wittiest and most innovative lyrical talents. For much of its history, Trinidad was a poorly fortified Spanish backwater with a reputation for carrying on a lucrative smuggling trade and an especially debaucherous Carnival season. In Port of Spain’s underworld, Trinidadian musicians played to audiences of pimps, prostitutes, and privateers, and they adopted numerous musical styles from the island’s diverse population, which included a Creole French bourgeoisie, Venezuelan planters, Afro-Caribbean slave labor, and the East Indians imported by the British, who took control of the island in 1797.

In the early 20th century, road march calypso, which developed as an accompaniment to the two months of Carnival parties, festivals, and parades, dominated the calypso scene. However, as the protestant British, averse to the rampant carousing of the Catholic holiday gone rogue, enforced increasing restrictions on the festivities, the soloistic tent calypso rose in prominence. By the 1930’s, the period known as the Golden Age of Calypso, the calypso tent became a battle arena where calypsonians, notorious for their sly wit and indolent hedonism, came to demonstrate their legendary linguistic dexterity in improvised verbal duels and the twisting rhymes of their lyrical compositions. Taking flamboyant monikers such as Lord Invader, Attilla the Hun, and Roaring Lion, the Golden Age calypsonians were masters of the double entendre, and their songs extemporized on ribald scandals and current events. Their scathing political commentaries soon became a central focus of the British censorship offices, who were responsible for the destruction of hundreds of original Calypso records. Nonetheless, always insistent on having the last word, calypsonians found inventive ways to circumvent colonial restrictions and remained politically outspoken until Trinidad’s independence in 1962.