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I believe this post will become one of my favorites to write and share. Mark this date, June 22, 2025, as the day on "De Dotish Hour" Mr. Desmond threw out the big one: “Top 10 Calypsos of all time.” He wanted to know why creating a Top 10 Calypso list is so difficult. Kenny turned to Deso and made a face that resembled a "couyon mouth." As he responded to Mr. Desmond, his expression suggested that he was taken aback by the question—no, nearly short-circuited on hearing Deso's statement. Both Kenny and Vanessa (steelpan music arranger and radio host) questioned, “But what about the rest in the Top 100? Will you be considering the others as well? To which Deso responded emphatically, "No!" Deso's statement set sirens blaring!
Now, therein lies the ultimate challenge: selecting a Top 10 Calypso List. Good luck with that! But let's be fair to Deso; he wants a committee to be formed with the task of coming up with a formula and then selecting the Top 10.' Without a scientific formula, the process reverts to subjective decision-making. After the list is compiled, show it to someone from the other islands where Calypso is also part of their carnival history.
Choosing only 10 Calypso songs is very subjective because TUCO does not have records (not all great calypsos were recorded) or criteria for so doing. The result is that everyone knows what the Top 10 should be... and that is the problem! How can you condense the stories, culture, rhythm, and bacchanal into a list?
Ask ten Calypso fans to name their all-time top ten, and you’ll likely get ten different lists—and ten very passionate debates. Why? Calypso encompasses more than just music; it embodies history, wit, rebellion, joy, and identity, all encapsulated in rhythm.
Here’s the thing: creating a definitive Top 10 Calypso list is as rewarding as it is impossible. Here’s why (I am sure to get a verbal cutarse for this):
The Pros:
- Preservation of Legacy: It spotlights legendary artists and timeless messages. So true, and for that reason, Sokah2Soca is here, on the other side of the coin, with WACK Visual Radio.
- Cultural Education: New generations get a guided tour of lyrical brilliance. This generation's lack of familiarity with calypso is so profound that it could almost be considered a sin.
- Celebration of Craft: It honors songwriting, performance, and ingenuity. Personally, I don't think songwriters receive the credit they deserve. Most of the time, you are unaware of who wrote the song, and the singer receives the credit. That is a travesty. Another thing is that the music arrangement/creative process is lost, and the singer gets all the praise.
The Cons:
- Subjectivity is deeply ingrained: what resonates in Port of Spain may not resonate in Bridgetown or Brooklyn. Mr. Desmond must accept this reality. If he is creating a "Top 10" for Trinidad and Tobago, fine. Then again, callers to the station like "De Alcoholic" and historians like Steven will share bois for sure when he announces his "Top 10."
- Time Bias: Do we weigh the classics from the 50s and 60s more than modern genius? This is a real dilemma, for sure. Every generation has its unique moments of brilliance, so how can we select the top performers across the decades? Technology and population size matter, don't they?
- Exclusion Hurts: Narrowing to ten means omitting beloved voices—and fans will notice. Not only will this cause hurt feelings, but Trinidadians collectively believe they possess a deeper understanding of calypso, steelband, and soca than their neighbors, a fact that is often overlooked!
Deso, Kenny, and—perhaps more cautiously—steelpan arranger and radio personality Vanessa Headley all weighed in on the challenge of creating such a list. On Sokah2Soca, I’ve already shared a “Top 100 Calypsos of All Time,” but to explore the debate over a definitive “Top 10,” I turned to an AI service for reference points. Big mistake—but a revealing one. It confirmed what I’ve said repeatedly: AI still doesn’t grasp the nuances of Caribbean culture. Errors plagued the results, including incorrect song titles and misattributed artists. So I went back to the roots, revisiting the carefully curated lists I’ve published on Sokah2Soca. Trust me, Deso, Kenny, and the Calypso faithful will scrutinize and criticize my selections. And honestly? That’s the whole point of this post.
This discussion isn’t about finality—it’s about sparking conversation. The songs listed here are simply starting points. While Deso prefers not to put his name on any official list, I was told his real aim in posing the question was to encourage much-needed dialogue. Personally, I don’t believe a true “Top 10” is even possible—without set guidelines or some kind of scientific method, it’s all wildly subjective. That said, there’s no harm in stirring things up, especially since this whole debate was ignited on “De Dotish Hour Show” on WACK Visual Radio. So rather than one list to quarrel over, we’re offering you two. Double the cussing, double the fun—C’est La Vie!
Chart A: The Canonized Greats
This list pays homage to pioneers, political firebrands, and lyrical legends.
- “Jean and Dinah”—The Mighty Sparrow
- “Rum and Coca-Cola” —Lord Invader
- “The Road”—Lord Kitchener
- “Die with my Dignity” —Singing Sandra
- “The Caribbean Man”—Black Stalin
- “High Mass” —David Rudder
- “Portrait of Trinidad” —Sniper
- “Bassman”—Shadow
- “Progress”—King Austin
Chart B: The Heartbeats & Road Favorites
These songs were chosen due to their enduring popularity and ability to captivate the dance floor.
- “Sugar Bum Bum” —Lord Kitchener
- “Lorraine”—Explainer
- “Bun Dem”—Stalin
- “In Time to Come” —Crazy
- “Endless Vibrations”—Lord Shorty
- “This Melody Sweet”—Baron
- “Soucouyant”—Crazy
- “Free Up”—Tambu (Christopher Herbert)
- “Rock It”—Merchant
- Woman on the Bass—Scrunter
Two lists. Each list holds ten spots. And still, it doesn’t feel like enough. Who’s missing? Who would you bump up or add? Maybe that is the point Kenny Phillips was trying to make to Mr. Desmond during their conversation. If you choose a subjective score of ten, how do you evaluate the remaining entries in the disputed Top 100 Calypsos of all time? The conversation will surely continue...
I was hoping to include a mixtape from Mr. Desmond in the post, but I haven't heard back from him yet. If he does send a mix, I will add it to the post. In the meantime, I've included a YouTube video featuring several well-known classic calypsos. We’d love to hear your thoughts!
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Production Notes/Music Credits:
Topic Discussed: The Calypso Conundrum: Can We Really Choose a Top Ten of All Time?
Origin: Trinidad, Republic of Trinidad & Tobago
Genre: Calypso?
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