I first came across with calypso when I bought a calypso LP full of names like Lord Melody, King Rudolph, The Lion and Lord Kitchener. Calypso comes from Trinidad and Tobago. And as the dear wikipedia tells us the first official calypso song was recorded 1912 by Lovey's String Band. Calypso came from the earlier kaiso -music.
The calypso lyrics were very often very political and talking about the corruption. There were people also dumping the censored calypso plates to the sea. Some of the most known calypso singers were: Attila the Hun, Roaring Lion, Lord Invader and Lord Kitchener. A song "Rum and coca-cola" from Lord Invader came well known because it's cover by The Andrew Sisters in 1944.
And a remix version of the Andrew Sisters version with a great video:
Later on Harry Belafonte made calypso more known, but with more commercial style.
"Jump in the line"