20th-century Trinidad and Tobago male singers

Slinger Francisco ORTT CMT OBE (born July 9, 1935), better known as Mighty Sparrow, is a Grenadian calypso vocalist, songwriter, and guitarist. Known as the "Calypso King of the World", he is one of the best-known and most successful calypsonians. He has won Trinidad's Carnival Road March competition eight times, Calypso King/Monarch eight times, and has twice won the Calypso King of Kings title.

Machel Montano (born 24 November 1974) is a Trinidadian soca singer, actor, record producer and songwriter. Known for his high energy, fast-paced, and often unpredictable on-stage performances, he is one of the genre’s most popular artists in the world.

Leslie Sebastian Charles, MBE (born 21 January 1950), known professionally as Billy Ocean, is a Trinidadian-British recording artist who had a string of R&B international pop hits in the 1970s and 1980s. He was the most popular Trinidad–British R&B singer-songwriter of the early to mid-1980s. After scoring his first four UK Top 20 successes, seven years passed before he accumulated a series of transatlantic successes, including three US No. 1's. His 1985 hit "When the Going Gets Tough, the Tough Get Going" reached No. 1 in the UK and No. 2 in the US. In 1985, Ocean won the Grammy Award for Best Male R&B Vocal Performance for his worldwide hit "Caribbean Queen (No More Love on the Run)" and in 1987 was nominated for the Brit Award for Best British Male Artist. His 1988 hit "Get Outta My Dreams, Get into My Car" reached No. 1 in the US and No. 3 in the UK. His 1986 hit "There'll Be Sad Songs (To Make You Cry)" also reached No. 1 in the US.

Nestor Alexander Haddaway (born 9 January 1965) is a Trinidadian-born German vocalist and musician best known for his 1993 hit single "What Is Love", which reached number 1 in 13 countries.

Wintley Augustus Phipps, Sr. (born January 7, 1955) is a Trinidadian-American singer, songwriter, record producer, and minister, and founder of the U.S. Dream Academy, Songs of Freedom Publishing Company, and Coral Records Recording Company. He features a booming baritone voice, usually singing inspirational gospel music. He is an ordained Seventh-day Adventist minister.

Aldwyn Roberts HBM DA (18 April 1922 – 11 February 2000), better known by the stage name Lord Kitchener (or "Kitch"), was a Trinidadian calypsonian. He has been described as "the grand master of calypso" and "the greatest calypsonian of the post-war age".

David Michael Rudder (born 6 May 1953) is a Trinidadian calypsonian, known to be one of the most successful calypsonians of all time. He performed as lead singer for the brass band Charlie's Roots. Nine years later, Rudder stepped outside the band, entering the calypso tent as a solo calypsonian in 1986, which was followed by an unprecedented rise to fame.

Edwin Ayoung (born 1944), better known as Crazy, is a Trinidadian calypsonian. He has been active since the mid-1970s and is one of the most successful artists from Trinidad and Tobago.

Leroy Calliste (24 September 1941 – 28 December 2022), better known as Black Stalin, was a leading calypsonian from Trinidad and Tobago 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.

Lancelot Victor Edward Pinard (March 24, 1902 – March 12, 2001) was a calypso singer and actor who used the name Sir Lancelot. Sir Lancelot played a major role in popularizing calypso in North America, and Harry Belafonte has acknowledged him as an inspiration and major influence.