Top 10 Calypso Music Artists

Calypso is a style of Caribbean music that originated in Trinidad & Tobago during the early & mid-19th century & spread to the rest of the Caribbean Antilles by the mid-20th century. Its rhythms can be traced back to West African Kaiso & the arrival of French planters & slaves from the French Antilles in the 18th century.
The Top Ten
1 Harry Belafonte

The man that popularized the calypso genre worldwide with his 1956 album Calypso & his songs Matilda, Jamaica Farewell, Mary's Boy Child & his cover of Day Da Light (as the Banana Boat Song) & Jump in the Line (Shake, Senora). He was the king of calypso. R.I.P. (1927-2023).

2 Jimmy Buffett

He was known for his hit Margaritaville, which led to co-founding a restaurant chain in its honor. He had a net worth of $1 billion at the time of his death, making him the only calypso artist to be a billionaire as well as its richest singer. R.I.P. (1946-2023).

3 Arrow

He was known for his song Hot Hot Hot, which David Johansen/Buster Poindexter and the Vengaboys covered. R.I.P. (1949-2010).

4 "King" Eric Gibson
5 Black Stalin

A leading calypsonian from Trinidad and Tobago, he was known for his lyrics against European colonial oppression. He won the Calypso Monarch competition on five occasions and the Calypso King of the World title in 1999. R.I.P. (1941-2022).

6 Freddy Grant

A British Guiana-born jazz and calypso artist, he played the saxophone and clarinet. He was active in Great Britain before moving to the U.S.A. R.I.P. (1905-1986).

7 Ajamu

A Grenadian calypsonian, his music covers several Caribbean styles, including calypso, soca, and reggae. He held the title of Grenada Calypso Monarch nine times in 1987, 1988, 1990, 1991, 1992, 1995, 2004, 2014, and again in 2015, giving him the most crowns in Grenada Calypso.

8 David Rudder

A Trinidadian calypsonian, he is known to be one of the most successful calypsonians of all time. He performed as the lead singer for the brass band Charlie's Roots.

9 André Toussaint

A Haitian singer and guitarist, he emigrated to Nassau, Bahamas, in 1953 and performed there until his death in 1981. He sang and recorded in several languages and in a variety of styles, including calypso. R.I.P.

10 Lord Creator

Kendrick Patrick (also known professionally as Lord Creator) was a Trinidadian artist specializing in calypso, R&B, ska, and rocksteady. Alongside Cuban-born Roland Alphonso, Barbadian Jackie Opel, and fellow Trinidadians Lynn Taitt and Lord Brynner, Lord Creator was an important and positive "outside" influence during the early development of the Jamaican music scene. R.I.P. (1935-2023).

The Contenders
11 Calypso Rose
12 Chalkdust

A leading calypsonian from Trinidad and Tobago who has been singing calypso since 1967 and has recorded more than 300 calypso tracks.

13 Byron Lee

The lead vocalist of the band Byron Lee and the Dragonaires, who contributed to popularizing Caribbean music worldwide. R.I.P.

14 Denyse Plummer
15 Denzil Botus

A pannist from Trinidad who is best known for holding the record for most winning steel band Panorama arrangements and his heavy jazz influence in calypso/soca music.

16 Destra Garcia
17 Shango

Clifton George Bailey III, better known by the stage name Capleton, King Shango, Fyah Man, Prophet, is a Jamaican reggae and dancehall artist.

18 Anslem Douglas

A composer who is best known for his song Doggie (Who Let the Dogs Out), which the Baha Men covered.

19 Atilla the Hun

Raymond Quevedo, better known as Atilla the Hun, was a calypsonian from Trinidad who was one of the pioneers in spreading awareness of calypso beyond its birthplace in Trinidad and Tobago. Rest in Peace (1892-1962).

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