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2019
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Daddy Chess
Daddy Chess is a Dominican calypsonian from Virgin Lane, Roseau. He takes his first Calypso Monarch crown in 2001, a year after his calypso debut.
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The tracks
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
"Bumpa Fete" (2019) is Daddy Chess with who?
"Bumpa Fete" (2019): Daddy Chess with Cornell Phillip.
Bet #2
Where is Daddy Chess from?
Daddy Chess is from Virgin Lane, Roseau, Dominica.
Bet #3
Which of these three is active in Dominica?
Daddy Chess is active in Dominica.
0/3
The sound of the moment is right here:
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
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The thread
Year by year
2001
2 facts
First Calypso Monarch crown of Dominica. YouTube, Daddy Chess, Love Bouyon Talks
First Calypso Monarch crown of Dominica.
2026
1 release
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
Dominican carnival grand slam: Calypso Monarch (14 February 2026), King of the Tent and Road March with "Roof Leaking".
Discography
Where to listen
The circle1 collaborators
Sourced musical collaborations · Other bouyon voices from Dominica · In the same circle · The story behind the name · Understand bouyon
Sourced musical collaborations
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
UnderstandThe story
Who Daddy Chess is · Read the full story · Frequently asked questions
Daddy Chess is a Dominican calypsonian from Virgin Lane, Roseau. He takes his first Calypso Monarch crown in 2001, a year after his calypso debut. A quarter of a century later, in 2026, he pulls off a grand slam: Calypso Monarch (crowned February 14, 2026), King of the Tent and Road March with "Roof Leaking".
His family belongs to the Swinging Stars circle, one of Dominica's big dance bands: his father played drums there. On stage he comes from soca, and he stands for a calypso that holds its own, next to Bouyon. In the studio, by his own account, it is Cornell Phillip, WCK co-founder, who tells him to drop a reggae-marked way of singing and make his own style.
Daddy Chess is not a Bouyon artist: he is a calypsonian, a stage neighbour of the genre.
Daddy Chess is not a Bouyon artist, he is a calypsonian from Roseau, Dominica. He takes his first Calypso Monarch crown in 2001, a year after his debut, then in 2026, a quarter of a century later, pulls off a Dominican carnival grand slam: Calypso Monarch, King of the Tent and Road March with "Roof Leaking".
His family belongs to the Swinging Stars circle, one of Dominica's big dance bands: his father played drums there. On stage he comes from soca, and he stands for a calypso that holds its own, next to Bouyon. In the studio, by his own account, it is Cornell Phillip, WCK co-founder, who tells him to drop a reggae-marked way of singing and make his own style.
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, the features 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 2000, from Virgin Lane, Roseau, Dominica. The profile also lays out the releases, the features, 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 PROOF4 sources
All 4 sources, one by one
Sources
-
Dominica News Online, Daddy Chess adds Road March title to his 2026 Calypso reign
2026 carnival grand slam: Calypso Monarch, then Road March with "Roof Leakin", 101 plays on the road.
https://dominicanewsonline.com/news/homepage/news/__trashed-6/ -
Dominica News, Daddy Chess crowned as Dominica's 2026 Calypso Monarch
Finale on February 14, 2026 at Windsor Park Sports Stadium. Second crown, 25 years after the first (2001, a year after his 2000 debut).
https://www.dominicanews.dm/news/chester-daddy-chess-letang-crowned-as-dominica-s-2026-calypso-monarch -
YouTube, Daddy Chess, Love Bouyon Talks Ep. 6 (interview)
Love Bouyon Talks interview, March 1, 2026 (34 min 07): first crown 25 years ago, Swinging Stars family (father a drummer), Cornell Phillip's studio advice, lapo kabwit initiation in secondary school.
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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