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The Calypso Monarch (originally Calypso King) contest is one of the two major annual Calypso music competitions held in Trinidad and all English speaking Caribbean islands, as part of the annual carnival celebrations.
While calypso had been traditionally a male preserve, the contest was won in 1978 by Calypso Rose, prompting the organisers to crown her 'Calypso Monarch', the gender-neutral title remaining from that day. There was not another female winner until Singing Sandra took the crown in 1999.Ferguson, Isaac (1999) " Trinidad's Women Set Tone of '99 Carnival", Billboard, 20 March 1999, p. 8, 87. Retrieved 16 September 2013 Singing Sandra is the only female calypsonian to win the Calypso Monarch twice. She won the crown again in 2003.
The late Mighty Duke is the only calypsonian to have won the title on four consecutive occasions between 1968 and 1971.
Rastafari calypsonian Black Stalin won the title on five occasions between 1979 and 1995.O'Brien, Glenn (1985) " Calypso", Spin, June 1985, pp. 42-45. Retrieved 16 September 2013
The contest is limited to Trinidad & Tobago nationals; however, similar Calypso Monarch contests are now held annually in other Caribbean countries and also in North America and the United Kingdom.Mason, Peter (1998) Bacchanal!: The Carnival Culture of Trinidad, Temple University Press, , p. 51
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| 2018 | Helon Francis | "Change" | 1st |
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| 2020 | Terri Lyons | "Obeah", "Meghan My Dear" | 1 |
| 2023 | Duane Ta'zyah O'Connor | "Sing Hallelujah" | 1 |
| 2024 | Machel Montano | "Soul of Calypso" | 1 |
| 2025 | Helon Francis | "To Whom it May Be" | 1st |
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