Mighty Shadow obituary

In the flamboyant world of calypso, Mighty Shadow, who has died aged 77, stood out as an eccentric counterpoint to the colourful norm. On stage, typically clad in dark cape and wide-brimmed black hat, he would perform with a slight frown while either standing still or moving in jumpy, jerky movements as his deep, tremulous voice conveyed a vulnerability that was matched by songs of personal frailty and wild imaginings.

It was a persona and outlook that stood in dramatic contrast to the classic bravura of the typical calypsonian, one that might have been expected to generate either bemusement or scorn in his native Trinidad and Tobago. But in fact it proved so original, so eerily amusing and so engaging that Shadow quickly came to be hailed as one of the greats.

Given that Trinidad is the birthplace of calypso, and that calypso music is the backbone of the country’s most important cultural touchstone, the annual carnival, Shadow’s greatness in that sphere was more important than it might appear to the casual observer.

Two of the most vital elements of carnival are the Calypso Monarch competition, in which judges decide who is the best calypsonian of the season, and the Road March title, awarded to the purveyor of the song most played on the streets by revellers during carnival. Shadow won both – the Calypso Monarch crown in 2000 and two Road March titles, one in 1974 and the other in 2001.

His best known song, Bassman, which won him the 1974 Road March crown, announced him as a potent alternative to the hitherto dominant forces of calypso, Mighty Sparrow and Lord Kitchener, and was also one of the earliest examples of soca – a more uptempo, electrified version of calypso that has ruled the roost in the Caribbean ever since.

Shadow was born Winston Bailey in the Belmont area of the Trinidadian capital, Port of Spain, and grew up with his grandparents, Evlan and Elly Bailey, in Les Coteaux, a village in Tobago much associated with the African spiritualism of obeah, the atmosphere of which could often be detected around his music.

His grandfather, a small-time farmer, was also a choirmaster, and it was he who taught Winston the rudiments of singing. He also began learning the guitar at 15, and the following year left home to establish himself as a calypsonian, using Shadow as his moniker after he heard a road worker being addressed by that name and felt it “was something that suited me”.

Living in some of the poorest parts of Port of Spain and working occasionally as a carpenter, Shadow initially found it easier to sell his songs to other calypsonians than to persuade promoters to put him on the bill in his own right – not just because his demeanour was so strange but because he also suffered from stage fright and a lack of confidence.

Eventually, however, he was taken under the wing of the leading calypsonian Lord Blakie, who, in 1971, gave him a slot in his Victory calypso “tent” – a venue set up to showcase songs for the upcoming carnival season. There were hiccups along the way – Shadow would sometimes simply refuse to come out and perform – but in general the wry, abstract humour of his delivery and lyrics proved hugely popular with audiences, and gradually his confidence improved.

Within three years he had produced Bassman, in which he sang about his helpless possession by a hideously catchy steel pan bass-line. Having planned to “forget calypso and go plant peas in Tobago”, Shadow finds that “Every night I lay down in me bed/ I hearing a bassman in me head”. He visits a brain surgeon for help (“A man in me head/ I want him to dead”) but is sent away and has no option but to return to a life of music, revealing to the world the tune that has bugged him so much.

It was a strange construction for a calypso, yet it chimed beautifully with listeners – after all, everyone has had some form of bassman in their head – and its dark, if lighthearted, edges of madness and inner turmoil gave an insight into Shadow’s restless, real-life obsession with music. Crucially, and naturally, it also had an irresistible bass-line – one that henceforth encouraged a much greater focus in calypso and soca on what Shadow called the “bottom of the music”.

Bassman guaranteed lifelong affection for its creator, and is still played as regularly today as it was when it was released. But Shadow also followed up with other popular gems, including Feeling the Feeling (1989), Poverty Is Hell (1994) and Dingolay (also 1994), the latter an uplifting and heartfelt tribute to the life-enhancing power of music.

Although he won calypso titles with less regularity than some others (there was a widespread suspicion that judges disliked his weirdness, and as a result he boycotted the Calypso Monarch competition for 17 years), in the public perception Shadow was what his fellow calypsonian David Rudder called “our uncrowned king”. This stood him in great stead across a five-decade career in which he made more than a dozen albums and, from 1979, ran his own Master’s Den calypso tent, which brought forth some of Trinidad’s best new calypso talent. “Mighty” was added to Shadow’s stage name not by the artist himself, but by popular acclaim.

Nonetheless he lived for most of his life in humble circumstances, latterly in the Mount Lambert area just outside of Port of Spain, where he continued to succumb to his fixation with song, often going to bed at 6pm before waking in the middle of the night to write music. “I’m a slave to what I’m doing,” he said. “I can’t stop – then I would really go mad.”

He was awarded Trinidad’s Silver Hummingbird medal in 2003 for his contribution to culture, and died shortly before he was due to receive an honorary degree from the University of the West Indies.

He is survived by five children.