Black Stalin, who has died aged 81, was a modern calypsonian of the old school, dedicated to keeping political and social commentary at the heart of his music when other exponents of the art were becoming purveyors of frivolous party music. His determination to stick to what he saw as the righteous course allowed Stalin to become calypso monarch in his native Trinidad and Tobago – the highest achievement any calypsonian can aspire to – on five occasions. It also brought him a global audience of fans who were appreciative of his acerbic, Rasta-influenced take on political and racial affairs.
In the 1990s in particular Stalin was a force on the world music scene, and some of his many albums sold in significant quantities abroad. He was fiery by nature as well as in his lyrics, and among his best known songs were the classic Burn Dem (1987) – in which he begged Saint Peter to allow him to personally throw various world leaders, including Ronald Reagan and Margaret Thatcher, into the fires of hell – and More Come (1994), in which he celebrated an endless stream of black “warriors” ready to die in the battle against oppression.
Such compositions stood in marked contrast to the trend for dance-based “bump and wine” calypsos that took hold in Trinidad and the wider Caribbean from the 80s onwards – and which threatened to undermine the proud calypsonian tradition of creating music with a political edge.
While Stalin knew as well as anyone that calypso has often been leavened with humour, sexual innuendo and good dance tunes, he appreciated that social and political commentary was at its heart. And although he was not above issuing the odd feelgood tune himself – two of them, Black Man Feeling to Party, and Look on the Bright Side, won him the Calypso Monarch competition in 1991 – in general he stuck to his guns.
His body of work, generally stronger in meaning than in melody, was a mix of optimism and pessimism, often defiant and upbeat (as in his popular We Can Make It, from 1988, which encouraged Trinidadians to stand firm during an economic crisis) but just as frequently bemoaning the human condition (as in Ism Schism, from 1985, which despaired of the cynicism of politicians and the propensity of the electorate to fall for their tricks).
Though ethnic identity was a preoccupation, and he referred to himself mainly just as “The Black Man”, Stalin was scornful of those who played what he called “race politics” and stood aside from the black power movement that threatened revolution in Trinidad in 1970. Instead he positioned himself as a voice of the poor, of whatever race.
Born Leroy Calliste to Elcina, a market vendor, and her husband, George, in San Fernando in the south of Trinidad, he had a humble upbringing in the most impoverished part of town. Receiving only a cursory education at San Fernando Roman Catholic boys’ school, he spent much of his youth hanging around the practice yard of one of the local steelbands, the Free French Steel Orchestra, where he formed the idea of becoming an entertainer.
After school there were a number of short-lived jobs, including as a clerk at the Point-a Pierre docks and as a limbo dancer. Showing little interest in a conventional career path, he was increasingly drawn to San Fernando’s calypso “tents” – where a roster of calypsonians showcase their latest compositions to the paying public, especially in the run-up to carnival.
He made his singing debut at the Good Shepherd Friendly Society Hall in his home town in 1959 with the self-penned tune Why I Want to Be a Calypsonian, and by 1962 had found a regular home with the Southern Brigade tent in San Fernando, where he came under the wing of one of the most popular calypsonians of a previous generation, the fearsome Lord Blakie, who gave him the sobriquet Stalin. Although Calliste was too much in awe of Blakie ever to ask him why he had chosen the name, many later thought it suited his occasionally abrasive and dictatorial style, though he had a softer side to his personality too.
Calliste became well enough established to join an early 60s tour of calypsonians around the Caribbean, and by 1964 he was appearing at the Original Young Brigade tent in the Trinidadian capital, Port of Spain, run by the greatest of all calypsonians, Mighty Sparrow.
In the small economy of Trinidad, most calypsonians at that time regarded the idea of releasing records as an aspiration rather than an expectation. So although in 1966 Stalin issued his first single, he busied himself in subsequent years mainly with live performances – including a 1972 tour to New York – allied to yearly tilts at winning the calypso monarch competition, which offered the prospect of decent prize money.
It took him until 1978 to find a financial backer to release his first album, To the Caribbean Man, material from which helped to win him his first calypso monarch crown in 1979. For the next decade many of Stalin’s lyrics were informed by Rastafarianism and he began to come to the attention of the wider world, making his first European tour in 1987. He won his second calypso monarch crown in 1985, followed by others in 1987, 1991 and 1995, by which time albums such as Rebellion (1994) and Message to Sundar (1995) – both on Eddy Grant’s Ice Records label – were meeting with critical approval across the globe.
The height of Stalin’s activity and acclaim was from the late 70s to the early 2000s, but he managed to release a final album, Just for You, in 2009. Although he suffered a stroke in 2014, which left him unable to sing publicly, he maintained his status as one of Trinidad’s most beloved entertainers.
He is survived by his wife, Patsy (nee Mitchell), whom he married in 1974, by their three children, Shaka, Keina and Abiola, and by two sons, Jason and Ray, from an earlier relationship.
• Black Stalin (Leroy Calliste), singer, born 24 September 1941; died 28 December 2022
