2026
Roof Leaking
2026 Road March winning song
Bouyon blog · Artist profile
Daddy Chess
Dominican calypsonian · heritage · Virgin Lane, Roseau, Dominica · 2001-présent
4Sources
Daddy Chess, Chester Letang, is a Dominican calypsonian from Virgin Lane, Roseau. He takes his first Calypso Monarch crown in 2001, then, a quarter of a century later, pulls off a 2026 grand slam: Calypso Monarch (crowned 14 February 2026), King of the Tent and Road March with "Roof Leaking", a return to the top hailed by the Dominican press as the peak of a twenty-year journey. His family is rooted in the Swinging Stars circle, one of Dominica's big dance bands. It is that ground, bands, calypso, cadence, that surrounds the birth of Bouyon without being the same thing. In the studios, Daddy Chess crosses shared figures: by his own account, it is Cornell Phillip, WCK's sonic architect, who tells him in session to drop his imitation of a Jamaican model and find his own voice. His profile lives here as a heritage marker: a leading calypsonian whose path lights up the Dominican musical landscape around Bouyon, without making him an artist of the genre.
THE GAME
The bet
Think you know Daddy Chess? Three questions, let's find out.
5 facts about Daddy Chess. The first one is free, go all the way, your gift awaits 🎁
Fact #1, on the house: , First Calypso Monarch crown of Dominica. YouTube, Daddy Chess, Love Bouyon Talks
1/5
Bet #1
Where is Daddy Chess from?
Daddy Chess is from Virgin Lane, Roseau, Dominica.
Bet #2
Which of these three is active in Dominica?
Daddy Chess is active in Dominica.
Bet #3
Which of these three has been active since 2001 or earlier?
Daddy Chess: first documented trace in 2001.
0/3
The bonus fact: , Dominican carnival grand slam: Calypso Monarch (14 February 2026), King of the Tent and Road March with "Roof Leaking". Dominica News Online, Daddy Chess adds R
The sound of the moment is right here:
The bouyon dropping nowTHE STORY
Who Daddy Chess is
Daddy Chess, Chester Letang, is a Dominican calypsonian from Virgin Lane, Roseau. He takes his first Calypso Monarch crown in 2001, then, a quarter of a century later, pulls off a 2026 grand slam: Calypso Monarch (crowned 14 February 2026), King of the Tent and Road March with "Roof Leaking", a return to the top hailed by the Dominican press as the peak of a twenty-year journey.
His family is rooted in the Swinging Stars circle, one of Dominica's big dance bands. It is that ground, bands, calypso, cadence, that surrounds the birth of Bouyon without being the same thing. In the studios, Daddy Chess crosses shared figures: by his own account, it is Cornell Phillip, WCK's sonic architect, who tells him in session to drop his imitation of a Jamaican model and find his own voice.
His profile lives here as a heritage marker: a leading calypsonian whose path lights up the Dominican musical landscape around Bouyon, without making him an artist of the genre.
- Role
- Dominican calypsonian · heritage
- Origin
- Virgin Lane, Roseau, Dominica
- Period
- 2001-présent
- Genres
- Calypso · Cadence-lypso
- Territories
- Dominica
Where to listen
Daddy Chess is not a Bouyon artist, he is a calypsonian from Roseau, Dominica, and his profile lives here as a heritage marker. Chester Letang takes his first Calypso Monarch crown in 2001, then in 2026 pulls off a Dominican carnival grand slam: Calypso Monarch, King of the Tent and Road March with "Roof Leaking". The island's press hails a return to the top after a twenty-year journey.
His family belongs to the Swinging Stars circle, one of Dominica's big dance bands, the ground of bands, calypso and cadence that surrounds the birth of Bouyon without being the same thing. In the studios, Daddy Chess crosses figures shared with Bouyon: by his own account, it is Cornell Phillip, WCK's sonic architect, who tells him in session to drop an imitation and find his own voice.
So he stays at the edge of the story: a leading calypsonian whose path lights up the Dominican musical landscape around Bouyon, without making him an artist of the genre.
Frequently asked questions
Where is Daddy Chess from?
Daddy Chess is from Virgin Lane, Roseau, Dominica. This profile then follows the whole run: the dated timeline, the releases and the circle of artists around them.
How old is Daddy Chess?
This profile does not give Daddy Chess's age: no verified birth date is documented here. What is documented: active since 2001, from Virgin Lane, Roseau, Dominica. The profile also lays out the releases, the circle of artists around them.
Who is Daddy Chess?
Daddy Chess is not a Bouyon artist, he is a calypsonian from Roseau, Dominica.
What are Daddy Chess's key tracks?
Key tracks by Daddy Chess: "Roof Leaking" (2026). The profile gives the dates and the sources for each one.
THE CATALOG
What's playing
Listen now
My Bouyon New Waves playlist
Standout releases
THE NETWORK
The circle
Other bouyon voices from Dominica
In the same circle
The story behind the name
Daddy Chess appears in these chapters of the bouyon story.
Understand bouyon
THE TIMELINE
The dates
Year by year
-
First Calypso Monarch crown of Dominica. YouTube, Daddy Chess, Love Bouyon Talks
-
Dominican carnival grand slam: Calypso Monarch (14 February 2026), King of the Tent and Road March with "Roof Leaking". Dominica News Online, Daddy Chess adds R
THE PROOF
The sources
Sources
-
Dominica News Online, Daddy Chess adds Road March title to his 2026 Calypso reign
2026 carnival grand slam (Calypso Monarch + Road March).
https://dominicanewsonline.com/news/homepage/news/__trashed-6/ -
Dominica Gazette, Daddy Chess Captures 2026 Road March Title with "Roof Leaking"
2026 Road March won with "Roof Leaking" (101 road plays).
https://dominicagazette.com/daddy-chess-captures-2026-road-march-title-with-roof-leaking/ -
YouTube, Daddy Chess, Love Bouyon Talks Ep. 6 (interview)
Interview: first crown in 2001, Swinging Stars circle, Cornell Phillip's studio advice, Lapo Kabwit initiation.
https://www.youtube.com/watch?v=z4QfYC_R1DM -
Wikipedia, The Swinging Stars (Dominica)
Dominican dance band (formed 1959), Daddy Chess's family circle.
https://en.wikipedia.org/wiki/The_Swinging_Stars
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Hits & New Releases 2026 · curated by TIITII NBA
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