Black Stalin (born Leroy Calliste on September 24, 1941 in San Fernando, Trinidad and Tobago) is a leading calypsonian. Stalin began singing calypso in 1959, but did not join an calypso tent until 1962 when he joined the Southern Brigade. In 1967 he joined Kitchener's Calypso Revue tent and managed to place in that year's Calypso Monarch competition. Stalin won the Calypso Monarch competition for the first time in 1979 and went on to win it again in 1985, 1987, 1991 and 1995.