Leroy Calliste was born on the 24th of September 1941, popularly known as Black Stalin, he was born and raised on Coffee Street in San Fernando to George and Elcina Calliste, and he attended San Fernando Boys’ R.C. School. He was given the nickname Black Stalin by fellow calypsonian Blakie in the mid-1960s. He is a leading calypsonian from Trinidad and Tobago known for his militant Rastafarian and Black Nationalist lyrics.
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”.
His debut came in 1959 at Saint Madeline’s Good Sheppard Hall, but it was not until 1962 he joined a calypso tent (The Southern Brigade), although his work had previously come to the attention of the art-form’s senior players.
In 1967 he was cast at Kitchener’s Calypso Revue and graduated to national significance by earning a place in the annual calypso competition, pitting him against stalwarts like Lord Melody, Cypher, Young Killer and Composer for the $1,000 prize.
Two years later, he made the grade and convincingly, singing “Caribbean Man” and “Play One”, the latter a tribute to pan pioneer Winston “Spree” Simon. His 1979 win, the first such triumphs at the national level, therefore should be seen not just as a trophy on the shelf.
What it marked was the arrival at the top rung of a very different kind of calypsonian. It was no cakewalk. In fact, his victories have always come in spectacular fashion, their value heightened by the fact that he simply never won from a poor field.
In 1979 he was up against Explainer’s “Kicksing in Parliament” and “Dread”, the combination everyone swore would take the title. Also on that stage were Crazy, Short Pants, Relator, Singing Francine, Bro Valetino and Poser, who went on to win the road march title.
In 1985 he won the crown again with “Ism Schism” and “Wait Dorothy”, and again in 1987 with a tribute to steel band entitled “Mr. Pan maker” and “Bun ‘Em”,a song calling for St. Peter to cast the likes of Christopher Columbus, Cecil Rhodes, Margaret Thatcher and Ronald Reagan into Hell.
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 Feeling’ to Party”.In 1995 he went chutney, with a “Tribute to Sundar Popo”, in honour of his old friend and fellow singer.
A five-time winner of Trinidad’s National Calypso Monarch competition (1979, 1985, 1987, 1991, and 1995), Stalin sings of the struggles of South Africa, the quest for world peace, his secrets for staying alive (“stay strong, high and dread”) and the craft of pan drum making.
His disarming smile and gentle manner mask a razor-sharp wit, one that has conspired with a bag of memorable and highly interactive songs, to help him win fans the world over.