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Originally Posted by Oriphiel
Belafonte is the man.
Edit: If I had to recommend just one album of his, it'd be "Jump Up Calypso"...
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But the album "Calypso" was pretty popular in it's time, and I love the album cover because at a glance it kinda looks like he has seven fingers on his left hand. 
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Both of those are great albums, especially the second one. An interesting piece of trivia about them though is that they're not actually calypso despite the titles. The style of music on those albums is mento, but the record label simply labelled all carribean music as "calypso" back in the 50s. This was done because they were marketed to an American audience and Americans knew the word "calypso" but not the word "mento".