Education
He attended San Fernando Boys" Roman Catholic School.
He attended San Fernando Boys" Roman Catholic School.
Born and raised on Coffee Street in San Fernando to George and Elcina Calliste, he is one of four children. He worked as a limbo dancer before taking up singing calypso in 1959 when he made his debut at the Good Shepherd Hall in Saint 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.
In 1979 he moved over to the Mighty Shadow"s King of the Wizards Tent and recorded his first album, To the Caribbean Manitoba 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 1994 he signed with Eddy Grant"s Ice Records label, releasing the Rebellion album that year and Message to Sundar in 1995. Black Stalin became Doctor Leroy Calliste on 31 October 2008, when he was conferred with an honorary doctorate from the University of the West Indies, Saint Augustine, for his tremendous dedication and contribution to Calypso music and culture in Trinidad and Tobago.
He has won the Calypso Monarch competition on five occasions and the Calypso King of the World title in 1999. Stalin won the Calypso Monarch competition for the first time in 1979 (with "Caribbean Manitoba" and "Play One") and went on to win it again in 1985, 1987, 1991 and 1995. 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 "Econometrica", a song calling for Saint 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. 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 "Black Manitoba Feeling to Party" and "Wine Boy", poking fun at the politician Dhanraj Singh.