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
Harry Belafonte

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

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 the genre's richest singer. R.I.P. (1946-2023).

Arrow

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

"King" Eric Gibson
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 five times and the Calypso King of the World title in 1999. R.I.P. (1941-2022).

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 USA. R.I.P. (1905-1986).

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, winning in 1987, 1988, 1990, 1991, 1992, 1995, 2004, 2014, and 2015, giving him the most crowns in Grenada Calypso.

David Rudder

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

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 a variety of styles, including calypso. R.I.P.

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 Newcomers

? Lord Kitchener
? Shango

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

The Contenders
Calypso Rose
Chalkdust

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

Byron Lee

The lead vocalist of the band Byron Lee and the Dragonaires, who helped popularize Caribbean music worldwide. R.I.P.

Denyse Plummer
Denzil Botus

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

Destra Garcia
Anslem Douglas

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

Atilla the Hun

Raymond Quevedo, better known as Atilla the Hun, was a calypsonian from Trinidad and 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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