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Shurwayne Winchester was born on February 8th, 1974 in Tobago. He is undoubtedly blessed with a singer's voice, a quick wit and an ability to make pictures with music. His talents first came to light in 1996, when he was only twelve years old and began competing in local calypso competitions, where he consistently placed within the top three. He participated in these local competitions until 1990, when he was encouraged to compete against seasoned veterans, such as Calypso Queen Denyse Plummer, Calypso Monarchs Cro Cro and Luta in the Carib Independence Calypso Competition.