Take Ten (part 2): the greatest calypso and soca singers of all time

Garry Steckles shares his personal list of the ten greatest calypso and soca singers of all time

  • Illustration by Darren Cheewah
  • Illustration by Darren Cheewah

As I promised — or should that be threatened? — at the end of my last column, I’m about to embark on another list. The previous one was my ten personal favourite reggae singers — with the emphasis on personal. This time around, it’s my ten favourite calypso and soca singers, and it comes with the standard disclaimer: an apology to the many wonderful artists who could be included but aren’t, and to their fans who will inevitably think I’ve lost my mind.

But before I get into the list, a sad task: a farewell salute to a musician who made a major contribution to soca and calypso, as well as to reggae. But the Caribbean owed much more than a musical debt to Kittitian Ras Tamboura Kitwana, who died recently. He was a grassroots educator, a noted historian, and a highly respected Rastafarian elder who championed the movement in the days — not so long ago — when its followers were often treated with suspicion and scorn by mainstream Caribbean society. He was also a true gentleman, in every sense of the word.

Tamboura was a leading member of the legendary Ellie Matt and the GI’s Brass, and then GI’s Brass International, who were widely regarded as two of the top bands in the Caribbean for much of the late 1970s and well into the 80s. He played percussion and sang, touring extensively — mainly in North America and Britain — in the days when the bands were at the peak of their popularity.

As an educator, Tamboura’s long-running radio programme Under the Banyan Tree was a living, breathing St Kitts and Nevis history lesson, as he shared his knowledge and wisdom with listeners. As one of the Eastern Caribbean’s most prominent Rastafarians, Tamboura was a pioneer of the movement in its early years, and was famous for being the first man with dreadlocks allowed into Dominica, in the days when many Caribbean nations refused to admit people with locks. Tamboura’s appearance on stage there attracted huge numbers of Dominica’s indigenous Rastafarian community to celebrate what was, for them, a momentous occasion.

RIP, Tamboura, and I wish you were around to tell me where I might have gone wrong with the following list.

In no particular order:

David Rudder

I wasn’t being entirely truthful when I said this would be in no particular order. The following nine names, sure — but when a performer is known as the “Lyrics Man” in a genre renowned for scintillating lyrics, he has to be something special, and David Rudder, in my humble opinion, is not only the greatest calypsonian of them all, but one of the greatest musicians, period.

In a career that dates back to the 1970s, Rudder has steered calypso and soca in new and uncharted directions, and at the same time has used his gifts to celebrate the music’s roots, its history, and the revered performers of yesteryear. The issues Rudder addresses range from West Indies cricket (“Rally Round the West Indies”) to the horrendous aftermath of the Rodney King trial (“LA”) to the election of Barack Obama (“Party on the Mall”); from the delights of his beloved homeland (“Trini 2 De Bone”, “The Ganges and the Nile”) to police brutality (“Forty-one Bullets”) and the history of calypso (“Calypso Music”, “The Ministry of Rhythm”).

Personal favourite song: a tough one, so I’ll take the easy way out and pick Rudder’s latest single, “Unity”, recorded with the hugely popular Trinidadian band Kes, and with a line in it that’s right up there with the Lyrics Man’s best: “Live your life like yuh playing mas.”

The Mighty Sparrow

Arguably the most popular calypsonian ever, Slinger “Sparrow” Francisco exploded on the Caribbean music scene in 1956 with “Jean and Dinah”, a deceptively raunchy number with an instantly addictive melody line that won him the first of his eight Trinidad and Tobago Calypso Monarch and Road March crowns.

Blessed with a voice that can switch seamlessly from the most ribald of calypsos to the sweetest of ballads, Sparrow ruled the genre through the 60s and 70s, regaling us with songs like “Ah Fraid Pussy Bite Me”, “Melda (Obeah Wedding)”, “Mas in Brooklyn”, “Drunk and Disorderly”, “Royal Jail”, “Sa Sa Yea”, “Congo Man”, “Lying Excuses”, “Sixty Million Frenchmen”, and “No Money, No Love”.

Personal favourite song: “Mr Walker”, in which Sparrow, in hot pursuit of a rich man’s daughter, trots out some of his most outrageous lines, along with snatches of poignant social commentary.

Lord Kitchener

The beloved Kitchener, a uniquely gifted songwriter, composed many of the most enduring melodies in the history of calypso. Apart from having a warm and distinctive voice, with just a hint of fragility, Aldwyn Roberts — known to his legions of fans simply as Kitch — had an endearing personality and movie-star good looks. His instantly hummable melodies brought him a record eleven Trinidad and Tobago Road March titles — and an even more staggering eighteen of his compositions were the vehicles that won the coveted steelband Panorama crown, including a run of eleven consecutive years from 1967 to 1977.

Personal favourite song: there have been so many, and I was sorely tempted to choose the double entendre masterpiece “Dr Kitch”. But I’ll settle for “Mas in Madison Square Garden”, a celebration of calypso and its place in the hearts of Caribbean people living outside the region.

The Mighty Gabby

Barbados’s most accomplished calypsonian, Anthony “Mighty Gabby” Carter has been making memorable music since the late 60s, with hard-hitting lyrics, melody lines that last, and frequent excursions into innovative areas beyond the traditional confines of calypso.

Personal favourite song: again, a tough choice, as Gabby’s discography includes classics such as “Emmerton”, “Gisela”, “Jack”, “Chicken and Ram”, “Massa Day Done”, and “In de Savannah”, but my vote has to go to “Windforce”, a 1989 hit that was a strong contender for that year’s Road March crown at Barbados Crop Over.


One of calypso’s unique voices — gruff, growly, and still perfectly pitched — Macdonald “Grynner” Blenman has a limited recorded output. But Barbados’s beloved “Ugly Man” (as he calls himself) has a gift for coming up with catchy songs that make people sing along and dance — a gift that has brought him a record seven Road March crowns at Crop Over.

Personal favourite song: I love just about everything I’ve heard by Grynner, with “Bajan Yankee”, “We Want More”, and “Get Out de Way” among the very best, but the hands-down winner in my book is the wonderful “Leggo I Hand”, Barbados’s 1989 Road March, which features one of calypso’s most memorable lines: “Jah Rastafari para jambo creator of rhythm and tempo master of the sweet calypso leading I band.”


The aptly named Winston “Explainer” Henry would be on my top ten calypsonians list if the only song he’d ever written and recorded was his sublime 1981 hit “Ras Mas”. Fortunately, Explainer has made dozens more memorable recordings, many of them biting social commentaries, in a career that dates back to 1969 — the most popular of them being 1982’s “Lorraine”, the story of a homesick Trinidadian leaving his better half behind as he heads to the land of calypso to take part in Carnival.

Personal favourite song: Simple. “Ras Mas”.

Ras Shorty-I

Acclaimed as the man who created soca, Garfield “Ras Shorty-I” Blackman was much more than a formidable and hugely popular musician. He started his career as the calypsonian Lord Shorty, and was known as one of the wildest men in a genre known for hard-living lifestyles, before adopting a new name and a new philosophy on life, becoming deeply religious and retreating with his family into the forests of southern Trinidad. In his latter years, Shorty focused on making faith-based music, much of which reflected the influences of Trinidad’s Indian population, with whom he had grown up.

Personal favourite song: “Watch Out My Children”. A simply sublime melody with words to match, this warning about the dangers of cocaine was embraced by the United Nations as part of an anti-drug campaign.


High-octane soca with a wide range of influences that included zouk, salsa, and merengue was the musical signature of Montserrat’s Alphonsus “Arrow” Cassell, one of the best-loved and most influential artists to emerge from the Caribbean. Arrow, whose “Hot, Hot, Hot” remains the biggest international soca hit ever, and was adopted as the anthem of the 1986 football World Cup in Mexico, was also renowned as a high-energy and charismatic stage performer.

Personal favourite song: again, a difficult choice, but I have to go for “Hot, Hot, Hot”, in all its different incarnations.

Andre Tanker

I’m not one hundred per cent sure if Andre Tanker should be described as a calypsonian. I am one hundred per cent sure he could be described as a superlative, one-of-a-kind musician who blessed us with music that was heavily influenced by calypso and soca, even if he plied his trade — with considerable success — outside the mainstream of either genre. He had a wonderful voice, full of vibrant character, and a gift for rhythmic structure that could only be described as unique.

Personal favourite song: “Sayamanda” is hands-down Tanker’s most popular composition, but my personal choice would have to be “Steelband Times”, a jazzy, quirky, and quite wonderful ode to the steel pan and the people who play it.

Calypso Rose

Without question the greatest female calypsonian of them all, McCartha “Calypso Rose” Lewis has done more, much more, than make wonderful music during a career dating back to the mid-60s. She was the first woman to win a Road March crown at Trinidad Carnival, in 1977. The following year, she went one better and won the Calypso King competition — leaving Carnival officials with no choice but to rename the genre’s most prestigious contest, which has been the Calypso Monarch ever since. Her voice, when she’s belting out an up-tempo soca number, is a powerhouse, hitting and holding notes that leave you shaking your head in disbelief. And she’s just as comfortable with a soulful ballad.

Personal favourite song: “Voodoo Lay Loo”, from Rose’s landmark 1977 album Her Majesty Calypso Rose.


Funding provided by the 11th EDF Regional Private Sector Development Programme Direct Support Grants Programme.
The views expressed on this website are those of the the authors and do not reflect those of the Direct Support Grants Programme.