Friday, May 1, 2026

Jerry Roberts: 23 years of calypso

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Jerry Roberts is like a cat with nine lives. No matter how many times people write off his tent as a failure he springs right back and surprises them year after year by opening. He admits, though, it hasn’t been easy.

It is his love for music that drives him and even though he comes close to being broke after every Crop Over season, he wouldn’t change it for anything.

He loves the St Philip-based Stray Cats calypso tent and pours his heart and soul into it to make sure that people who want a stage to perform, have it.

In a chat with EASY magazine on a day that started out gloomy before the clouds gave way to dazzling sunshine, he said that people often ask him why he doesn’t just shut down the tent that started in the early 1990s, especially since he only gets a handful of sponsors.

“I keep coming back because people think I will fail,” he said in a serious tone. “Everybody says, ‘I see you in the paper every Crop Over and ask ‘How you do it.’ When people try to lick you up, it gives you that extra push . . .”, Jerry said.

And he manages the tent with a few faithful sponsors.

“I try to do the music first because that’s the most important thing and sometimes I get so busy I don’t have time to look for sponsors. We have one of the best sponsors in Paul Doyle and the use of the Crane Resort. A guy saw me and told me how lucky I am. He asked how many calypso tents have some place like the Crane Resort to perform.

“I complain about sponsors but then I realised how lucky I am. We have Stoute’s Car Rentals, Gale’s Hatcheries, So-Lo, Emerald City, Cutters, and Douglas Trotman who has been a supporter,” he said before breaking into laughter.

It is not unusual for him and tent mate Anthony De Cheerman Walrond to write songs but Jerry goes a step further and arranges the music (he can’t write music), sometimes pays to get it scored, and also

pays for recording time to push the members of his tent.

He explained that it was after a bad experience in a defunct tent that he started Stray Cats so that other people wouldn’t have to go through what he did.

His niece Joy-Ann Roberts is back in the tent, making him even more motivated. He also has a funny memory from 1995 when he was booed at the first Party Monarch competition.

“I wouldn’t move and Joy-Ann came out and wuk up and then I sing my song sitting in a chair with the one-man band and then they hollered, ‘The judges ain’t ready’ By then she could hardly walk and was limping,” he said, laughing.

Jerry added: “You’ve got to love music. I love music and I was playing from the time I was eight years old. In those days I couldn’t afford a guitar so I made guitars and did so at the age of 14. I started out with Blue Rhythm Combo and went to Canada and stayed there for 18 years.

“I was a star for three months in Hollywood and they wanted me to get married and I run like hell and left everything,” he said, again laughing heartily.

He headed back to Barbados broke, unmarried, but soon had to leave again because he couldn’t find a job.

Back in Canada he drove a taxi before playing for the Eskimos.

“You’ve got to love music and if people in Canada shoot at me on stage and I ducked because I said I ain’t moving, people in Barbados can’t do me anything. They’d have to kill me.

“Music keeps you alive too; that’s probably what has got me still living. I’m 68 and I don’t feel it,” he asserted.

The snickering and disrespect doesn’t bother him one bit . . . . He is past that now. He knows that even though people have come and gone over the years, if he fails to open the tent door, then some people who are interested in the art form might not get a chance anywhere else.

This is not to be interpreted as his being ready to take just any one. He wants people who are prepared to help out, listen and grow.

Going by the moniker Big Boar Cat, he has moved away from being a one-man band and has a group of talented youngsters he likes working with. It was noted that his plan from the get-go was to have young musicians involved in the tent and the festival.

The band this year has two trumpeters, two saxophonists, a drummer, a bass and a rhythm guitarist, keyboardist as well as The Kittens – the background vocalists.

Jerry praised his bandleader Keron Prescod, who arranged some of the songs and writes the notes. He said that “takes a load off”.

“That’s the chemistry that we have so when somebody comes into the tent and cannot afford the music [this is what we do],” he said.

The tent leader is grateful to the calypsonians who perform year after year and make the tent what it is. He singled out Annie Anna, who is a consistent performer; Khaddfi, who comes every year with a party tune; and De Cheerman, who plays an integral role as songwriter.

For those who don’t know, Stray Cats did land a calypsonian – Big Davy – in the Pic-O-De-Crop semi-finals but hasn’t done so since.

When all is said and done, Jerry, a former student of Christ Church Foundation School, is not daunted. He knows how hard life can be as his schooldays were not easy because he was dyslexic.

He is contented with the progress he’s made over the years and will continue to play his music and scratch his way to success and happiness. (GBM)

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