Veteran Trinidadian calypsonian Explainer dies at 74

The Trinbago Unified Calypsonians Organization (TUCO) says that veteran Trinidadian calypsonian Winston “Explainer” Henry went to the Great Beyond on Oct. 7. He was 74.
“It is with great sadness that we announce the passing of composer, calypso extraordinaire, icon and father, Winston ‘Explainer’ Henry, who departed this life, today 7th October, 2022,” said TUCO in a statement.
It said Explainer, who was born on Nov. 13, 1947, was the father of three children – Wendell, Stageann and Winston.
“He was affectionately dubbed the messenger because he composed songs which expressed the ills of society and the oppression of the poor man,” TUCO said.
It said Explainer started singing calypso in 1969, “which gave him a lifelong career of 43 years, and shot to fame when he joined an Ace Producer Mr. Rawlston Charles who produced memorable tunes like ‘Ras Mass’ and the immortal ‘Lorraine’, just to name a few.”
TUCO said “Lorraine,” a “highly infectious song, was, indeed, a hit with locals and fans abroad.
“In fact, ‘Lorraine’ made it to the British charts at position number 35,” it said.
In Explainer’s 50-plus years in the calypso arena, TUCO said he produced great hits and collaborated with Bunji Garlin, Blaxx, Maximus Dan and Farmer Nappy.
It said Explainer composed for many artistes, and was a mentor to young calypsonians, including Devon Seale, Karene Asche, Rondell Donawa, Chuck Gordon, Erphaan Alves and Victoria Cooper.
As a cultural ambassador, TUCO said Explainer took calypso around the world, performing in Europe, North America, South America and throughout the Caribbean.
He also performed in prestigious venues like the Common Wealth Institute in London, and The Apollo Theatre, Madison Square Garden, Studio 54 and the Brooklyn Academy of Music.
TUCO said that, in 2018, Explainer was the recipient of Trinidad and Tobago’s Hummingbird Medal-Gold National Award for his contribution to the cultural artform.
Explainer was last attached to Kaiso House Calypso Tent and was a member of the TUCO calypso monarch adjudication committee, TUCO said.
“On behalf of the president, general council membership of TUCO and the wider cultural fraternity, we extend condolences to his family, loved ones, friends and fans in this time of mourning,” the statement said. “May He Rest in Peace.”
On his website, Explainer had written that his calypso career began in 1967, making his debut on Scouting for Talent with the late Holly Betaudier.
Then, two years later, he proceeded to the Southern Brigade Calypso Tent, which was managed by the late Edwin Peters.
In 1970, having that urge to be recognized nationally, Explainer wrote that he was taken to the late Lord Kitchener by Emorold Phillip (Valentino) and was accepted on the cast of The Calypso Revue the said year, where he sang from 1970 – 1974.
Being an admirer of the Mighty Sparrow, who was also his mentor, Explainer joined the Sparrow’s Original Young Brigade (OYB) in 1975, singing his first popular song, “Man and Wages,” followed by “Mr. African” in 1976, which took him to the National Semi Finals.
In 1977, Explainer sang “Caribbean Integration,” which took him to his first National Finals, after which he was no stranger to the Big Yard, because he made it to the National Finals 10 times, and, though not fortunate to win, was a favorite among his fans, with hits like “A Tribute to Maestro” in 1978.
Explainer wrote that he had a bumper season in 1979, with major hits like “Kicksin in Parliament,” “Sunday Night Fever,” “Yuh Got to Pay” and the first Raga Soca called “Dem Weh Dred.”
“From there on he never looked back and his name was on the lips of every Calypso lover,” the website said.
In 1980, after assessing the prize of an amateur competition “Scouting for Talent” in which the winner was paid more handsomely than the National Calypso Monarch, he decided to protest in song against the prize structure by singing “Not Me and the Monarchy” and “Table Turning.”
On hearing the song, Sissons Paints decided to increase the prize money from TT$1,000) to TT $12,000, Explainer wrote.
He said he stopped competing in 1998 because he recognized music as a “Mission and not a Competition.”