Leroy Calliste (24 September 1941 – 28 December 2022), better known as Black Stalin, was a leading calypsonian from Trinidad and Tobago known for his lyrics against European colonial oppression. He won the Calypso Monarch competition on five occasions and the Calypso King of the World title in 1999. Biography Born and raised on Coffee Street in San Fernando to George and Elcina Calliste, he is one of four children. He attended San Fernando Boys' R.C. School. He worked as a limbo dancer before taking up singing calypso in 1959 when he made his debut at the Good Shepherd Hall in St. Madeleine, but did not join a calypso tent until 1962 when he joined the Southern Brigade. He was given the nickname "Black Stalin" by fellow calypsonian Blakie in the mid-1960s. In 1967 Black Stalin 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 (with "Caribbean Man" and "Play One") and went on to win it again in 1985, 1987, 1991 and 1995. In 1979 he moved over to the Mighty Shadow's King of the Wizards Tent and recorded his first album, To the Caribbean Man. That year he walked away with his first Calypso Monarch crown for his two compositions, "Caribbean Unity" and "Play One". In 1985 he won the crown again with "Ism Schism" and "Wait Dorothy", and again in 1987 with a tribute to steelband entitled "Mr. Panmaker" and "Bun 'Dem", a song calling for St. Peter to cast the likes of Christopher Columbus, Cecil Rhodes, Margaret Thatcher and Ronald Reagan into Hell. In 1987 he was also awarded the Hummingbird Medal (Silver) for his contribution to Trinidad and Tobago culture. In 1991 the usually dread and critical Stalin took a winning turn and walked away with the Calypso Monarch crown again, with "Look on the Bright Side" and "Black man Feelin' to Party". In 1995 he went chutney, with a "Tribute to Sundar Popo", in honour of his old friend and fellow singer. In 1994 he signed with Eddy Grant's Ice Records label, releasing the Rebellion album that year and Message to Sundar in 1995. After finishing as runner-up to Mighty Sparrow in 1985, in 1999 Black Stalin won the title of Calypso King of the World with the calypsoes "Ah Feel to Party" and "Wine Boy",