According to Jacob Edgar, resident ethnomusicologist for Putumayo Records, an American record company that specializes in Caribbean and other world music, calypso's political and social overtones are comparable to those in today's rap music. Even early calypso chantwells, or lead singers, such as Boadicea and Hannibal, used the music to deliver commentaries about the onerous actions and policies of the colonial government. Much like early rap, the often-improvised lyrics were a means of communication. There is some question as to the origins of the word calypso. There are others who contend that the word comes from the Homer epic The Odyssey, which featured the nymph Calypso.
Debate also continues over the origins of calypso music.
Most music experts believe that calypso can be traced back to the gayup, or communal work song practiced by West African slaves who were not allowed to speak in the fields. Others say it is derived from French Caribbean troubadors who would travel throughout Europe in medieval times spreading news and stories. The first calypso recordings date to 1914, with the genre's heyday peaking in the 1930s. Some of the big names during those years were Roaring Lion, Attila the Hun, Lord Executor, and Mighty Destroyer. These calypso musicians often dressed in elaborate costumes and incorporated a variety of stage effects to stand out amongst their rivals.