Calypso is a style of Afro-Caribbean music that originated in Trinidad and Tobago from African and European roots. The roots of the genre lay in the arrival of enslaved Africans, who, not being allowed to speak to each other, communicated through song. This forged a sense of community among the Africans, who saw their colonial masters change rapidly, bringing French, Spanish and British music styles to the island of Trinidad. The French brought Carnival to Trinidad, and calypso competitions at Carnival grew in popularity, especially after the abolition of slavery in 1834. While most authorities stress the African roots of calypso, in his 1986 book, Calypso from France to Trinidad: 800 Years of History, that veteran calypsonian, The Roaring Lion (Rafael de Leon) asserted that calypso descends from the music of the medieval French troubadours.

The modern music history of Trinidad and Tobago reflects the ethnic groups which form the current culture—French, Spanish, British, the African and New World nations from which the African population derives, and subsequent immigration from Asia and India in the late nineteenth and early twentieth century. A creole culture was formed, combining elements of hundreds of African ethnic groups, native inhabitants of the islands, Indian indentured labourers, and British, French and Spanish colonizers. French planters and their slaves emigrated to Trinidad during the French Revolution (1789) from Martinique, including a number of West Africans, and French creoles from Saint Vincent, Grenada, and Dominica, establishing a local community before Trinidad and Tobago were taken from Spain by the British. Carnival had arrived with the French, and the slaves, who could not take part in Carnival, formed their own, parallel celebration called canboulay.

David Michael Rudder (born 6 May 1953, Belmont, Trinidad and Tobago) is a calypsonian from Trinidad.

David Rudder is one of the most successful calypsonians of all time. In 1977, he joined Charlie's Roots, a leading band in Trinidad and Tobago, and spent many years as one of the band's vocalists. In 1986 he came to prominence with his album The Hammer, which produced two big hits: "The Hammer" (a tribute to the late pannist Rudolph Charles) and "Bahia Girl". This was followed in 1987 with "Calypso Music", a brilliant encapsulation of the history of calypso. In 1988 Rudder released what is widely considered his best album to date, Haiti, which included the title track, a tribute to the glory and suffering of Haiti; "Engine Room", which captured the energy of the steel band; and "Rally 'Round the West Indies", which became the anthem of West Indies cricket.

In 2008, Rudder did a Soca collaboration with fellow Trinidadian Machel Montano, "Oil and Music" on Machel's 2007 album Flame On.

Mighty Sparrow or Birdie (born Slinger Francisco, July 9, 1935, in Grand Roy, Grenada, West Indies) is a calypso singer, songwriter, and guitarist. Known as the "Calypso King of the World," he is one of the most well-known and successful calypsonians. He has won Trinidad's Carnival Road March competition eight times and has been named "Calypso Monarch" eleven times.

Sparrow was born in Grenada on July 9, 1935, but moved to Trinidad when he was one year old. His birth name is Slinger Francisco. He grew up in Port of Spain.^{[citation needed]}

He was first exposed to music through the choir in Catholic school, and became interested in calypso at 14 when he joined a steel band composed of neighborhood boys. He received his performing name "The Mighty Sparrow" during his early career:

In 1956, Sparrow won Trinidad's Carnival Road March and Calypso Monarch competitions with his most famous song, "Jean and Dinah". His prize for the latter was $40. In protest of the small sum, he wrote the song "Carnival Boycott" and attempted to organize other singers to boycott the competition. About half of the singers followed. Sparrow claims credit for succeeding improvements in the conditions of calypso and steelband musicians in Trinidad, as well as the formation of the Carnival Development Committee, a musicians' assistance organization. Sparrow refused to participate in the competition for the next three years, but he continued to perform unofficially, even winning another Road March title in 1958 with "P.A.Y.E."

Harold George "Harry" Belafonte, Jr. (born March 1, 1927) is an American singer, songwriter, actor and social activist. He was dubbed the "King of Calypso" for popularizing the Caribbean musical style with an international audience in the 1950s. Belafonte is perhaps best known for singing "The Banana Boat Song", with its signature lyric "Day-O". Throughout his career he has been an advocate for civil rights and humanitarian causes and was a vocal critic of the policies of the George W. Bush Administration.

Born Harold George Bellanfanti, Jr., at Lying-in Hospital, Harlem, New York, Belafonte was the son of Melvine (née Love) – a housekeeper of Jamaican descent – and Harold George Bellanfanti, Sr., a Martiniquan who worked as a chef in the National Guard. From 1932 to 1940, he lived with his grandmother in her native country of Jamaica. When he returned to New York City, he attended George Washington High School after which he joined the Navy and served during World War II. In the 1940s, he was working as a janitor's assistant in NYC when a tenant gave him, as a gratuity, two tickets to see the American Negro Theater. He fell in love with the art form and also met Sidney Poitier. The financially struggling pair regularly purchased a single seat to local plays, trading places in between acts, after informing the other about the progression of the play. At the end of the 1940s, he took classes in acting at the Dramatic Workshop of The New School in New York with the influential German director Erwin Piscator alongside Marlon Brando, Tony Curtis, Walter Matthau, Bea Arthur and Sidney Poitier, while performing with the American Negro Theatre. He subsequently received a Tony Award for his participation in the Broadway revue John Murray Anderson's Almanac.