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Caribbean Beat Magazine

Shadow: The Uncrowned King

Music-lovers may see Shadow as a king of soca and calypso, but the calypso judges don't think so. Debbie Jacob on a great enigma of Caribbean music

  • Trinidad’s Mighty Shadow. Photograph by Abigail Hadeed
  • Trinidad’s Mighty Shadow. Photograph by Abigail Hadeed
  • Trinidad’s Mighty Shadow. Photograph by Abigail Hadeed
  • Photograph by Abigail Hadeed
  • Photograph by Abigail Hadeed

The name Shadow is enough to light up the face of any true calypso fan. No other singer is more mysterious, mesmerising or controversial.

His music is famous for its bold bass line and its strange, offbeat stories: a bassman from hell who comes out to play; a diablesse (devilwoman) exposing her cowfoot to a horrified victim; Abyssinia, the most frightening blue-devil masquerader ever to demand money from spectators. There’s also a tender side which declares Music sweet and I believe in the stars above and Poverty is hell.

But Shadow was for decades an uncrowned king. Why Trinidad and Tobago’s calypso judges consistently overlooked him until 2000 is hard to explain. In the 70s, his music made more inroads in American black radio stations than any other calypsonian’s. He has been singled out by Walt Disney Productions, one of a small handful of calypsonians contributing to a special calypso compilation for children. But at home it is a different story.

Shadow stands in the living room of his humble Mount Lambert home outside Port of Spain, demonstrating how the youngsters dance to his 1995 song Donkey Cart. It tells of old-time days in Tobago, when La Diablesse captured unsuspecting men. Behind him, there’s a brass sculpture of himself in the days of his legendary Bassman, more than 20 years ago: the floppy hat, long trench coat and bell-bottom pants camouflage the pain of that night’s defeat. “A group of guys showed up on my doorstep a few years after Bassman. They said, ‘Here, we want you to have this because you never win nothing.’ They walked away and I laughed. That is good people.”

Since then, Shadow has won awards from NJAC, a small political party with strong cultural interests. His songs normally make the Top 20 calypso list every year. He hangs the awards over his door. His 1994 album Dingolay won a Caribbean Music Award for best engineered album. Sound engineer John Affoon recalls: “He said, This is the first major award I won, I go’ keep this!”

But never the crown that his many disciples feel he deserves. For years, Trinidadians thought that calypso judges would send him mad, or drive him back to Tobago to plant peas as he once threatened to do. But he has found away to survive. “I’m a slave to what I’m doing,” he laughs “I can’t stop — then I’d really go mad.”

It was a sultry Dimanche Gras night in 1974 when a young skinny singer named Shadow who was reinvigorating calypso with blistering bass lines, challenged the Mighty Sparrow for the Calypso Monarch title. His song Bassman had burst upon the calypso scene like no other song since Sparrow’s Jean and Dinah in 1956. In those days, calypso seemed to be divided into three categories: Sparrow, Kitchener and the rest. But Shadow’s name had emerged as a potent musical force of its own; he threatened to turn the existing hierarchy upside down. Everyone was haunted by a singer who could exert such power just by standing on stage, deadpan, and moving his shoulders or jumping an inch off the ground.

“I was a little boy who had just come into the Police Band and couldn’t play nothing more than the cowbell when Shadow came on stage to sing Bassman,” says musician Neville Brown. “From the time the bass guitarist played a chord the crowd went wild. You couldn’t hear anything in that Savannah. No one has ever matched that moment.”

Few other nights in calypso history have stirred up so much controversy. Twenty-one years later, people still remember its magic, and the disappointment as Sparrow snatched the crown.

Until 2000 Shadow was the only calypsonian remembered for not winning the crown. After that night, he became a legend: a dark mysterious character with a wry sense of humour, offbeat lyrics and a musical voice all his own. He became part of calypso folklore.

Today, his power over the public is stronger than ever. But his bad Iuck with the judges finally ended. For years, Shadow refused to set foot in the Savannah. In 1993, when the competition was held in the National Stadium, he tried again with Survival Road, but again the judges passed him by. In 1994, he looked set to win his first calypso crown with Pay the Devil, a tribute to the legendary masquerader Abyssinia, and a potent social commentary called Poverty is Hell. But, again, it was not to be.

“I was home, peeling an orange, when they made the announcement over the radio that the judges leave me right there in the semi-finals for the Calypso Monarch competition. I put down the orange, went in the bedroom, started to strum my guitar. I said, ‘Hey, it still workin’.’ Then I put down the guitar and started to suck the orange.”

Shadow is more philosophical than aggrieved these days. “Judges don’t worry me too much. They don’t try to understand. They remain in the past. They have to understand everything is based on change. Anyway, I can’t keep them in my head or else there’d be no place for my music. And I can’t make a tune for them.”

In 1995 he reached the semi-finals again, and sang a piece demanding to know why his crown had been stolen. This did not impress the judges either, and he failed to make the finals.

Shadow was born in Trinidad on October 4, 1941. His real name is Winston Bailey. He doesn’t remember when he went to Tobago. “All I know is I always liked the bush, the trees and breeze. I liked listening to the birds. I always looked at the sunset.”

He grew up with his grandparents Evlan and Elly Bailey until he was 14 (“I used to look after the cattle and sheep and donkeys”). The first music he remembers is the sound of wooden drums covered with goatskin. Heated over a coconut branch fire, these drums, always accompanied by a fiddler, were frequently heard weddings and other celebrations. “The first time I remember hearing calypso was when I was eight. I was so carried away. I knew from that moment what I wanted to do with my life.”

The house was full of music: his grandfather was a musician and choirmaster. “We used to be all right at home, but my life and happiness was really being out there in the bush. While other children used to be playing, I would be by myself bathing in the river all day.” He was close to his sister Maria, who was a year older than him. She was one of the select few who heard his first calypso.

“I used to listen a lot to people and their problems and I came up with this:

Imelda, you charge me wrongfully
I don’t know nothing about you and your boy baby
When I receive the citation I fell in a trance
But me ent paying any maintenance.

“Music was never difficult. In no time I’d come up with a sweet melody and lyrics loaded with rhythm.”

At 15 he began learning the guitar. “I left home from Les Coteaux to go to a village near Charlotteville. A man named Joseph Kerr taught me two basic chords. I played those chords until my fingers were sore.” Kerr was so surprised at the youngster’s progress that he showed him off to the neighbours. “He said, come let’s go up the road. I ent too feel to go because my fingers were hurting, but I said, this thing like a magic. And I got lots of encouragement from the people.” He still had no instrument of his own. “I used to make drums out of a bucket and play a bottle and spoon. Whenever I had to go for water, I’d turn over the drum and play it.”

Another strong musical influence was Carnival in Les Coteaux, which was filled with the traditional rhythms of the frightening blue devils. “I went to Carnival and found myself in a steelband. I said, ‘Give me a knock on that.’ There was a piece of brass shaped like a rum bottle and it had a good tone blending with the steel. I couldn’t give it back.” You can still hear that percussion in Shadow’s music.

When he was 16, Shadow caught a boat and went to Trinidad. He auditioned to sing in a calypso tent. “I remember singing and someone saying, a next Sparrow, but I still didn’t get to sing on stage. I was always good for the people but I couldn’t please the judges.”

While he struggled to get into a tent, he stayed in John John with his father, then moved to Laventille. “There I did all my research. I meditated and worked. I lived some kind of a how. Sometimes I got a little work. I wasn’t lucky getting jobs but I never did anything wrong.” He decided to learn carpentry but gave it up after nearly falling from a roof.

“I didn’t go back. I realised it had no music up there. I spent a lot of time not eating meat, and that was good for me spiritually.” Much of this time was spent alone, waiting for Carnival. “I tried all the tents, Kitchener, even the Original Young Brigade. I tried too early. I used to try too much.” He secretly wrote songs for calypsonians — he still won’t say which ones — who earned encores with them. “I wasn’t angry or sad or bitter about not getting in a tent. I just felt I had to go back and do more work.”

His first break did not come till 1970. Those were Black Power days in Trinidad, and the country was looking for a new sound. Calypso tent manager Syl Taylor of the Young Brigade saw what the public wanted in Shadow, and he won early notoriety with a song called Saltfish, a comic piece full of double entendre and innuendo.

“I had the crowd going from the first verse. By the second verse, every time I had to come in the crowd started to laugh, and I couldn’t come in. I went off stage to ask a friend for the second verse. I clean forget it. By the time I caught myself, they wouldn’t let me go back on stage.”

It took some determination to recover. He followed the tent to Point Fortin in south Trinidad. “They wouldn’t put me on, but I’d made up my mind to get on stage. When the MC walked off stage, I went to talk to Syl Taylor. I timed the MC good. I saw him watching me talk to Syl. I told the MC, ‘Syl said put me on.’

The MC said, But Syl said never put you on stage again.’ Finally, I convinced him. When the MC put me on, I saw Syl in the background looking angry. I called to him and said, Syl, watch a good calypsonian work.’ I went out and got seven encores.” Taylor wouldn’t forgive Shadow. When the tent returned to town, he refused to put him on stage again. “I got frustrated and went to Tobago. I said after all this work I had failed again. I didn’t really fail, but there were people stopping me. It was a sad, sad thing to go in the bush with all that music in me.”

But Shadow returned to Trinidad (“I was desperate. I wanted to get close to calypso”) with one thing in mind: to break into the calypso kingdom ruled by Kitchener and Sparrow. He came with a song called The Threat.

When he landed he heard that the calypsonian Blakie wanted him to sing in his calypso tent on Wrightson Road. It was 1971, and his first regular slot. “The first night at the tent I went dressed in a short pair of jeans and a T-shirt. I hadn’t combed my hair for a week. Blakie said, ‘You come to sing?’ I said, ‘Not tonight.’ I just wasn’t feeling it. I tried my best and I had failed. From there, I decided to deal with my feelings.”

The next night, the tent travelled to Naparima Bowl in south Trinidad. “When I got in the Bowl, I got nervous and scared. I remembered what had happened before. All the time I was strong and suddenly I got weak. It was like I was carrying the whole burden of my life in my hands. I tried to fix my nerves. I took a big drink of rum and I started to sing.”

Before he knew it, the place had gone wild with his song Modern Housewives. “They called me back and back but no matter, I couldn’t get back my confidence. I was supposed to feel really happy but I was confused. I felt it might only happen one night.”

All the while he was hiding The Threat in his pocket. Realising something special was happening, Blakie took Shadow to the late Art De Coteau, one of the great Carnival arrangers. Blakie and De Coteau were excited, but Shadow was unsure how people would react to a newcomer threatening their two beloved kings.

One night he decided to take the chance. “I was sick and perspiring, but I let go a piece of The Threat in the tent. Well, it’s been the same story since. I ent win but I still threatening.”

The following year he returned with Trouble and Obeah. The deep, dark side was emerging. “I sang: Before I came here my name was Boy Bill. I had the best orchestra in hell. The people weren’t listening so I came with Bassman.”

was a huge popular success. But Shadow was sceptical about winning. “I told Cro Cro, they don’t want me to come first, so I’ll come out last.’ Cro Cro said, don’t do that.’ I wanted to go out there and sing dead, but when I went out the music was peppy and hot. I remembered Cro Cro’s words. I stomped my foot, took a stroll around the stage, and by the time I got to the microphone picked it up calmly and sang my song.

When he lost that night, Shadow’s first concern was for his friend Cro Cro. “I couldn’t find him. I searched everywhere. Finally, I found him crying in Independence Square.”

The people took Bassman to the streets in 1974 and made him King of the Road, but Shadow could not shake off his rancour at the decision. He would come back to it again.

Something is mad, here in Trinidad.
They take it for fun, pushin’ me around
I want to catch those judges in Hell

Judges or no judges, Shadow has a big place in calypso history. His music helped to shape soca and cement its popularity; technically, it also helped to bring the bass line to the forefront.

His real success has been his cross-generation appeal, and a style which has leaned increasingly towards rapso (rap over soca lyrics) while retaining enough musical craft to earn the praise of traditional calypso pundits.

His lyrics can come from anywhere, anytime. Three guitars line a wall in his bedroom, ready for the muse, and a tape recorder lies waiting within arm’s reach of the bed. “I go to bed sometimes at 6 p.m.,” says Shadow, “and wake up in the middle of the night and start to write. I never feel restless when I wake up. I know I have something to do. When you stay away from the music, it stays away from you.”

The years he spent running the Master’s Den calypso tent gave Trinidad and Tobago some of its most unusual and colourful characters: Trinidad Rio, Cro Cro, Funny, Eagle, Count Robin, Cardinal, M’Ba and Gypsy. “Man got strong there in the Master’s Den,” Shadow says.

He took in an unknown fisherman with a dynamite song called Soca Baptist when no one in town would touch it with a ten-foot pole. When the Baptists protested and, it is rumoured, Dr Eric Williams sent a secret message asking Shadow to give Boy Blue the axe, he stood by the singer who, as SuperBlue, would become one of the biggest successes of the next 15 years. He introduced an American girl, Daisann McLane, Lady Complainer, to the stage and opened the way for foreign acts in calypso.

“Shadow is going to be remembered for his contributions to rhythm and melody, for his strangeness, his weirdness, that sense of obeah in his music, the theme of retribution, his dedication and obsession with the music,” says calypso expert Dr Gordon Rohlehr.

“For me the most powerful year for Shadow was Jump, Judges Jump. That year the whole insecurity of Trinidad’s music came out. Short Shirt from Antigua had Tourist Leggo, which was such a big threat that a ban on foreign calypsos for the Road March Race was enacted. There was a big clash in the Savannah while the controversy was going on. Short Shirt sang Tourist Leggo, then Sparrow came back and let go Shadow who completely overwhelmed everyone. He saved Trinidad.

“I was in the stands outside the Savannah that night. I had no money to go in but I and all end up inside the Savannah on the stage. People who had never climbed in their life scaled the wall and jumped on the stage. The people lifted him up. It was like he said, ‘Just in case all you forget, this is the house of music.'”

Calypso superstar David Rudder sees Shadow as the most African of calypsonians. “There are those who have the Indian influence in their music. I’m reggae and jazz and African mixed, but Shadow’s the pure, tribal vibe. He’s one of those fellows who’s holding the line between generations. A true artist will always hold that line no matter what their age. People still wait on Shadow before they pass a judgement on Carnival. There will always be people who can’t go through Shadow’s door because of his weird, off-key sense of humour and his unique way of visualising his world.”

Shadow revolutionised calypso with a restless spirit that guides him more than he guides the music. “I remember a song called The Heart,” Rudder says. “There’s one violin playing throughout the tune. That violin was one of the strangest, saddest sounds; and yet there’s Shadow shouting against that sadness, ‘I am the hardest.'”

People keep reaching out to Shadow as their uncrowned king. “Tell Shadow I know how good he is. Plenty people know,” Rudder says. “Not only how good he is, but how important he is.”

Shadow shrugs and sings another song from his 1995 album.

Everything is over the judges’ heads.
By the time they understand, I go be dead
And they still won’t understand.