Shadow

1941-2018

by Erin MacLeod

It was 1974, on Dimanche Gras, the Sunday night before the streets of Trinidad’s Port of Spain would be, as they are each year, filled with revellers for two full days. In a musical battle as important as any boxing match, legendary calypsonian Mighty Sparrow’s seventh Calypso Monarch Crown was in doubt. His challenger? A man who called himself Shadow. Bouncing up and down in a peculiar skip-rope dance that became his signature, Shadow conquered the crowd with a rhythm-driven song called “Bassman.” Arranged by Art DeCoteau, the unique song pushed the bass front and centre, bringing some funk to the calypso stage. Though the judges chose the elder – by only six years – statesman Sparrow as winner, this triumph was only for the evening.

Shadow took over the city the very next day, his “Bassman” and the less experimental yet still entertaining “Ah Come Out to Play” ringing out all over town. Pan and brass bands played the tell-tale track throughout Carnival Monday and Tuesday, which helped Shadow win what might be the more important crown: the Road March, a distinction chosen by throngs of masqueraders.

At the time, a Rolling Stone journalist named Michael Thomas detailed all the brouhaha of that night in a piece entitled “King of Calypso.” “But outside, in the thick of it,” he writes, “the mob wanted ‘Bassman.’ It was that infernal poom poom poom. It was perfect for jumping-up.” Throughout the capital of the two island nation could be heard, “never far away, the sound of a steel band approaching – just the rhythm at first, and then the melody as high and strident as a thousand singing telephones, getting louder, playing ‘Bassman.’”

What made this particular song so special was that it just felt different from everything else. “Before Shadow, you had a typical bassline,” explains David Rudder, who, along with being one of the most significant and well-loved calypsonians Trinidad has produced, is also a big Shadow fan. “When he arrived, it was a different style. I grew up being part of that movement that was swept up by Shadowmania. He just showed us a whole new way to see and feel.”

But who was this Shadow that took Carnival by storm? Born in 1941 as Winston McGarland Bailey in the Belmont neighbourhood of Port of Spain, but raised by his grandparents in Les Coteaux on the island of Tobago, the boy who became Shadow reportedly started writing calypsos at the age of eight, and by 15 was playing guitar. Looking for a larger audience, he returned to his birthplace at 16, and tried to get into music, struggling to make a living and at times facing homelessness. Ironically, only a few years before challenging him, Shadow first took the stage at the Mighty Sparrow’s calypso tent – the term for a venue dedicated to the genre, specific to the carnival season.

The origins of his name – he apparently heard some workmen calling each other Shadow – are not as interesting as his visual interpretation of its meaning. Dressed in iconic black, with a large hat, sometimes a cape and other times with a skeleton costume underneath, Shadow’s sartorial flourish was the result of a combination of influences. There was, of course, the mid-century American radio programme character of the same name, as well as the Midnight Robber carnival character – one most likely based in the West African griot storytelling tradition – who dresses in a Western-inspired black outfit and speaks in boasts and braggadocio.

Lawrence Waldron, art history professor, and creator of the Shadowlingo blog – a treasure trove for anyone who has an interest in Shadow or thinking seriously about popular music – adds to this perspective. “On the tail of the Black Power movement in Trinidad and Tobago,” explains Waldron, Shadow’s image was “to be an intra-racial and psychological coup. Just like he had flipped the music, he aimed to flip on its head the metropolitan, urbane mestizaje or creolité of the Port of Spain calypso establishment, tilting against it with unapologetic Tobago (i.e. rural) Afro-blackness and vastly expanded [it].”

Shadow’s work as an artist sits at a crossroads. His music is calypso – a genre whose history reaches back to the period of enslavement, retaining rhythms of Africa and providing cutting (though often veiled) criticism of colonial oppression – but it is also soca, which was officially invented by Ras Shorty I in 1972. Lord Shorty is considered the Father of Soca, but for soca to evolve, it needed Shadow’s 1974 “Bassman.” Its driving, infectious rhythm reaches towards what listeners now understand as soca as much as calypso. Soca, arguably a descendent of “Bassman,” has become a genre of music that looks to reach the international heights of dancehall and reggae any moment now, if the music-loving world could pay contemporary masters of the form like Machel Montano, Nailah Blackman and others adequate attention.

Shadow’s musical innovations were matched by his lyrical talent. Calypsonians tend to have a sobriquet – a character that they present on the stage – but Shadow, according to Trinidadian visual artist Christopher Cozier, pushed the limits. In “Bassman,” he explains, there’s a three-way discussion between Winston Bailey the man, his sobriquet Shadow and the sound of the bass guitar line. Farrell was the name of “the bassman from hell,” whose rhythms were “takin’ [Shadow’s] head for a pan-yard.” From that song onwards, creativity, innovation and not a small amount of absurdity (see “Toe Jam,” for example) was key to Shadow’s work. And, as Cozier observed himself, Shadow had the ability to whip a crowd into a frenzy, describing his own experience in the late 1970s: “The crowd kept storming the stage every time Shadow tried to sing. People went into a frenzy over Shadow.”

Rudder also remembers the talent Shadow had for lyrics. “He reflects our life and times in the strangest, most minimalist way,” he says. “I remember one year Mighty Duke was trying to write a philosophical calypso about life, and what it really means and so on, and he’s struggling with the lyrics. Shadow heard the conversation and he wrote a song called ‘What is Life?’ the next day.” The song contains questions such as, “Why all this struggling to survive? What is this sense in being alive?” alongside observations like “the trees grow big and strong just to be cut down.” From 1994’s “Poverty is Hell” to 2016’s “What You Come Here For?” and many before and in between, Shadow had a knack for addressing a huge range of issues and topics.

Waldron agrees that Shadow’s lyrics present a sort of metaphysics: “He was a philosopher poet,” he explains. “Untrained and natural, sitting and contemplating on his own the internal contradictions of authority, credentialed bodies, natural and social hierarchies, romantic pair-bonding, artificial intelligence, and even life and death themselves.”

“The way he told a story, so simple but so right,” Rudder describes. “You need to appreciate the fact that he said few words, but the way he said it, it made so much sense. He cut through all the crap.” It’s therefore not a big surprise that he was set to receive an honorary doctorate from the University of the West Indies at the time of his passing on October 27, 2018.

This lyrical talent and ability to move between genres served Shadow well and allowed him to stand the test of time. Whether due to his strangeness or his singular musical ability and challenging of expectations, he was rarely able to please the judges and commented on this fact in 1976’s “Jump Judges Jump.” Regardless, his songs were always popular: he was the people’s calypsonian.

For 17 years, he simply ignored competition, reportedly saying, “I never get no crown, but they can't touch my music. The Shadow music sweet too bad.” He returned in 1993, working his way up to a win as Calypso Monarch in 2000 with “What's Wrong With Me” and “Scratch Meh Back.” The very next year, he took the Soca Monarch and Road March crown (and the honor of being the oldest person to do it) for his irresistible soca “Stranger.” With commentary on safe sex alongside encouragement to “do your thing,” the tune found success on the road just as “Bassman” had 26 years earlier.

“Calypso is blues with a smile,” says Rudder, “and he did this really well. A lot of people have this idea that tradition means you have to go back and play what was done 50 years ago. It’s more drawing from it and creating something new. It’s like Shadow’s influence on me: I draw from it and create something new. Shadow is one of those people: at the end of the day I think it his body of work is testament to who he is and who we are.”

In a 1992 episode of the Trinbagonian television show Calypso Showcase, the host Alvin Daniell had the pleasure of interviewing Shadow. “It struck me just as I call your name that you used to be called Mighty Shadow, [but] you prefer to be called Shadow,” said Daniell. Winston Bailey, leaning back in his seat, shook his head and responded: “Never the Mighty, never the Mighty, only Shadow.” Preferring throughout his career to focus on the rhythms and the melodies – “I’m a singing man, not a talking man,” he once said – the man in black’s music spoke and still speaks for itself.


Illustration: André Gottschalk

One Last Note...

A celebration of important music figures we lost in 2018

“He just showed us a whole new way to see and feel.”

David Rudder