On the 23rd of October, the Caribbean lost one of its great musical icons, the calypsonian, The Mighty Shadow.
The Shadow had suffered a stroke a few days before and passed away two days before the University of the West Indies could confer upon him, most deservedly, an Honorary Doctorate of Letters in recognition of his great contribution to music.
The Shadow, (the label of the ‘Mighty’ was conferred by others), born Winston Bailey, in the Port-of-Spain suburb of Belmont, Trinidad, was raised in Les Coteaux, Tobago on his grandparents’ farm. In an interview years later, Shadow remembers hearing a calypso for the first time on a gramophone at an aunt’s home and being ensnared by the sound. He asked his aunt to replay the song again and again, instantly recognising that this was his calling in life; he was going to be a calypsonian.
Inspired by the sounds of his environs, the rehearsals of the choir conducted by his grandfather and the cadence of the Tobagonian fiddlers and goat skin drummers, Bailey, in his own words,” tried writing calypso.” His aspirations to make it as a calypsonian drove him back to Trinidad as a teenager where he experienced homelessness for a while.
In 1970, at the age of 29, Bailey, who, by now had adopted the sobriquet of The Shadow, got his first break when he appeared in Lord Blakie’s Victory Calypso tent. His immediate goal of breaking the stranglehold of the two icons of calypso, Lord Kitchener and The Mighty Sparrow, on the Road March crown, which they had dominated from 1965, was perceived by many as impossible.
In 1974, the man who claimed “that he came here to sing calypso” broke their reign with the first of many classics, Bassman. The calypso with the catchy refrain, “Everytime I lie down in meh bed, I hearing a bassman in meh head” launched the start of Shadowmania and the question of why wasn’t Shadow crowned the calypso monarch that year.
The consummate showman, The Shadow often appeared on stage fully attired in black, inclusive of a broad brimmed hat and cape, with his distinctive voice – there was never any doubt whom you hearing – belting out his superbly crafted songs, accompanied by excellent musical arrangements, which covered the gamut of social commentary, politics, comedy and of course, love.
The Shadow’s signature act was to often stand motionless in front of the microphone or to the side of it whilst singing, then suddenly burst into a series of “skipping rope” bouncing motions. At times he would mutter or ramble an undecipherable chorus, sending audiences into a frenzy.
The Shadow was soon the rising star on the calypso and soca scene, nipping at the heels of Kitchener and Sparrow, yet the Calypso Monarch crown eluded his grasp. The judges, whom he felt were biased against him, provoked him to sing that “he wished to catch them in hell,” and drove him to skip the competition for seventeen years.
In 1981, The Shadow, who having appeared previously in both Kitchener’s and Sparrow’s tent, launched his own Masters’ Den Calypso tent which attracted future calypso monarchs such as Gypsy and Cro-Cro, and Road March King, Super Blue. The Shadow, who, just before he launched into his second song in one Calypso Monarch Final, advised the judges “to put their pens down because they couldn’t judge him” was not wary of challenging the establishment or hierarchy of the calypso world. He understood that progress comes with change, which people tend to be afraid of.
Patrons to his tent in 2000, upon hearing his lamentation “What’s Wrong With Me?” – an enquiry of the judges as to why they wouldn’t award him the crown – and “Scratch Meh Back” pleaded with the self-exiled rebel to enter the monarch competition. Rather reluctantly, “they [the judges] weren’t interested in my music,” he relented and bowed to the pressure. Much to his shock and his adoring fan base, he was duly crowned the Calypso Monarch. The next year, The Shadow added another Road March Title, with “Stranger,” a song which also landed him the International Soca Monarch Title.
The Shadow, often considered eccentric, perceived music as his destiny, and pursued it relentlessly, to the oblivion of all else. He once regretted that there was not enough time to produce all the music he wanted to for the people; the music was for the people and not the judges, after all. He would often go to bed early in the evening to rise in the middle of the night to pursue “the music inside of me.”
The Shadow produced a multitude of albums and hits which sold very well in the competitive world of calypso and soca music. His many classics include Charlene, Dingolay, Poverty is Hell, Tension, Pay The Devil, Don’t Try Dat, Obeah, Goumangala and I Come Out To Play.
“I was planning to forget calypso
To go and plant peas in Tobago,
But I afraid I can’t make de grade,
Every night I lie down in meh bed,
I hearing a bassman in meh head,
Bumpty—bump …
If I don’t want to sing,
When he start to do his thing,
I don’t want to but I got to sing…” (Bassman – 1974)
The Shadow, a true maestro, the likes of whom we will never see again, has departed. We are grateful that he listened to the Bassman and for the body of work that he has given us.
