Calypso music
The first major stars of calypso started crossing over to new audiences worldwide in the late 1930s. Attila the Hun, Roaring Lion and Lord Invader were first, followed by Lord Kitchener, one of the longest-lasting calypso stars in history—he continued to release hit records until his death in 2000. 1944's "Rum and Coca-Cola" by the Andrews Sisters, a cover version of a Lord Invader song, became an American hit despite the song being a very critical commentary on the explosion of prostitution, inflation and other negative influences accompanying the American military bases in Trinidad at the time. Perhaps the most straightforward way to describe the focus of calypso is that it articulated itself as a form of protest against the authoritarian colonial culture which existed at the time.
Music of Jamaica
The basic elements of hip-hop—boasting raps, rival posses, uptown throwdowns, and political commentary—were all present in Trinidadian music referred to as Extempo Wars as long ago as the 1800s, though they did not reach the form of commercial recordings until the 1920s and 30s. Calypso like other forms of music continued to evolve through the 50s and 60s. When rocksteady and reggae bands looked to make their music a form of national and even international black resistance, they took calypso's example. Calypso itself, like Jamaican music, moved back and forth between the predominance of boasting and toasting songs packed with 'slackness' and sexual innuendo and a more topical, political, 'conscious' style.