The Calypso Monarch (originally Calypso King) contest is one of the two major annual calypso competitions held in Trinidad and all English speaking Caribbean islands, as part of the annual carnival celebrations.
While Trinidad's carnival has its origins in the 18th century, a singing contest was first held in 1911, when the Jubilee Establishment offered a prize for "the most original song on a local topic".[1] Further competitions were held after World War I, and the Calypso King contest was first held in 1939.[1] The first winner was Growling Tiger with "Trade Union", followed by Roaring Lion in 1940 and Mighty Destroyer in 1941.[1][2] After a break during World War II, it resumed in 1946, with Atilla the Hun winning the first of two consecutive titles.[1] Mighty Spoiler won the first of three titles in 1948, and Lord Melody the first of three the following year. The competition's most successful calypsonians, Mighty Sparrow and Chalkdust, have won the title eight and nine times respectively, the first in 1956, and the last in 1992 for Sparrow, and Chalkdust's reigns were between 1976 and 2017.[1]
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.[1][2] There was not another female winner until Singing Sandra took the crown in 1999.[3] Singing Sandra is the only female calypsonian to win the Calypso Monarch twice. She won the crown again in 2003.[4]
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.[5]
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.[6]
| Year | Winner | Winning song(s) | Title # |
|---|---|---|---|
| 1939 | Growling Tiger | "Trade Union" | 1 |
| 1940 | Roaring Lion | "Rise and Fall of the British Empire" | 1 |
| 1941 | Mighty Destroyer | "Adolf Hitler" | 1 |
| 1946 | Atilla the Hun | "Daily Mail Report" | 1st |
| 1947 | Atilla the Hun | "Million Dollar Jail" | 2nd |
| 1948 | Mighty Spoiler | "Royal Wedding" | 1st |
| 1949 | Lord Melody | "Glory Mama Glory" | 1st |
| 1950 | No competition held | ||
| 1951 | Lord Melody | "Jonah and the Bake" | 2nd |
| 1953 | Mighty Spoiler | "Bed Bug" | 2nd |
| 1954 | Lord Melody | "Second Spring" | 3rd |
| 1955 | Mighty Spoiler | "Pick Sense Out of Nonsense" | 3rd |
| 1956 | Mighty Sparrow | "Yankees Gone" | 1st |
| 1957 | Lord Pretender | "Que Sera Sera" | 1 |
| 1958 | Striker | "Don't Blame the PNM", "Can't Find a Job to Suit Me" | 1st |
| 1959 | Striker | "Ban the Hoola Hoop", "Comparison" | 2nd |
| 1960 | Mighty Sparrow | "Mae Mae", "Ten to One Is Murder" | 2nd |
| 1961 | Mighty Dougla | "Lazy Man", "Split Me in Two" | 1 |
| 1962 | Mighty Sparrow | "Model Nation", "Sparrow Come Back Home" | 3rd |
| 1963 | Mighty Sparrow | "Dan Is the Man in the Van" | 4th |
| 1964 | Mighty Bomber | "Joan and James", "Bomber's Dream" | 1 |
| 1965 | Sniper | "Portrait of Trinidad", "More Production" | 1 |
| 1966 | Mighty Terror | "Pan Jamboree", "Last Year's Happiness" | 1 |
| 1967 | Mighty Cypher | "Last Elections", "If the Priest Could Play" | 1 |
| 1968 | Mighty Duke | "What Is Calpyso", "Social Bacchanal" | 1st |
| 1969 | Mighty Duke | "One Foot Visina", "Black Is Beautiful" | 2nd |
| 1970 | Mighty Duke | "Brotherhood of Man", "See Through" | 3rd |
| 1971 | Mighty Duke | "Mathematical Formula", "Melvin & Yvonne" | 4th |
| 1972 | Mighty Sparrow | "Drunk and Disorderly" | 5th |
| 1973 | Mighty Sparrow | "School Days", "Same Time, Same Place" | 6th |
| 1974 | Mighty Sparrow | "We Pass That Stage", "Miss Mary" | 7th |
| 1975 | Lord Kitchener | "Tribute to Spree Simon", "Fever" | 1 |
| 1976 | Chalkdust | "No Smut For Me", "Ah Put On Meh Guns Again" | 1st |
| 1977 | Chalkdust | "My Way Of Protest", "Shango Vision" | 2nd |
| 1978 | Calypso Rose | "I Thank Thee", "Her Majesty" | 1 |
| 1979 | Black Stalin | "Caribbean Man (Caribbean Unity)", "Play One" | 1st |
| 1980 | Lord Relator | "Food Prices", "Take ah Rest Mr Prime Minister" | 1 |
| 1981 | Chalkdust | "Things That Worry Me", "I Can't Make" | 3rd |
| 1982 | Scrunter | "The Will", "Ah Lick E Thing" | 1 |
| 1983 | Tobago Crusoe | "Don't Cry Now", "South Africa" | 1 |
| 1984 | Penguin | "We Living in Jail", "Sorf Man" | 1 |
| 1985 | Black Stalin | "Ism Schism", "Wait Dorothy Wait" | 2nd |
| 1986 | David Rudder | "The Hammer", "Bahia Girl" | 1 |
| 1987 | Black Stalin | "Mr Pan Maker", "Burn Them" | 3rd |
| 1988 | Cro-Cro | "Three Bo-rats", "Corruption in Common Entrance" | 1st |
| 1989 | Chalkdust | "Chauffeur Wanted", "Carnival Is the Answer" | 4th |
| 1990 | Cro-Cro | "Political Dictionary", "Party" | 2nd |
| 1991 | Black Stalin | "Ah Feel to Party", "Look on the Bright Side" | 4th |
| 1992 | Mighty Sparrow | "Both of Them", "Survival" | 8th |
| 1993 | Chalkdust | "Misconception", "Kaiso in the Hospital" | 5th |
| 1994= | De Lamo | "31 Years Old", "Trinity Is My Name" | 1 |
| 1994= | Luta | "Good Driving", "Licensed Firearm" | 1st |
| 1995 | Black Stalin | "In Time", "Tribute to Sundar Popo" | 5th |
| 1996 | Cro-Cro | "All Yuh Look for Dat", "Deh Cyah Stop Social Commentary" | 3rd |
| 1997 | Gypsy | "Rhythm of a People", "Little Black Boy" | 1 |
| 1998 | Mystic Prowler | "Vision of T&T in the Year 2010", "Look Beneath the Surface" | 1 |
| 1999 | Singing Sandra | "Voices from the Ghetto", "Song for Healing" | 1st |
| 2000 | Shadow | "What's Wrong with Me", "Scratch meh Back" | 1 |
| 2001 | Denyse Plummer | "Heroes", "Nah Leaving" | 1 |
| 2002 | Sugar Aloes | "Contribution", "Jubilation" | 1st |
| 2003 | Singing Sandra | "For Whom the Bell Tolls", "Ancient Rhythm" | 2nd |
| 2004 | Chalkdust | "Trinidad in the Cemetery", "Fish Mongrel" | 6th |
| 2005 | Chalkdust | "A When I Vexed, I doh Rhyme", "In Town Too Long" | 7th |
| 2006 | Luta | "Check The Foundation", "Kaiso Kaiso" | 2nd |
| 2007 | Cro-Cro | "Nobody Ain't Go Know" | 4th |
| 2008 | Sugar Aloes | "Reflections" | 2nd |
| 2009 | Chalkdust | "My Heart and I" | 8th |
| 2010 | Kurt Allen | "Too Bright" | 1 |
| 2011 | Karene Asche | "Careful What You Ask For", "Uncle Jack" | 1 |
| 2012 | Duane O'Connor | "The Hunt Is On", "Long Live Calypso" | 1 |
| 2013 | Eric "Pink Panther" Taylor | "Travel Woe", "Crying in the Chapel" | 1 |
| 2014 | Roderick "Chucky" Gordon | "Wey You Think", "Wedding of de Century" | 1st |
| 2015 | Roderick "Chucky" Gordon | "The Rose", "I Believe" | 2nd |
| 2016 | Devon Seale | “Respect God's Voice”, "Spirit of Carnival" | 1 |
| 2017 | Chalkdust | "75 can't go into 14" | 9th |
| 2018 | Helon Francis | "Change" | 1 |
| 2019 | Ronaldo London | “Imagination” | 1 |
| 2020 | Terri Lyons | "Obeah", "Meghan My Dear" | 1 |
| 2023 | Duane Ta'zyah O'Connor | "Sing Hallelujah" | 1 |
| 2024 | Machel Montano | "Soul of Calypso" | 1 |
Only a few Calypsonians have the honour of being crowned multiple-time monarchs.
| Winner | Years | # of titles |
|---|---|---|
| Atilla the Hun | 1946-1947 | 2 |
| Mighty Spoiler | 1948, 1953, 1955 | 3 |
| Lord Melody | 1949, 1950, 1954 | 3 |
| Mighty Sparrow | 1956, 1960, 1962–1963, 1972–1974, 1992 | 8 |
| Striker | 1958-1959 | 2 |
| Mighty Duke | 1968-1971 | 4 |
| Chalkdust | 1976–1977, 1981, 1989, 1993, 2004–2005, 2009, 2017 | 9 |
| Black Stalin | 1979, 1985, 1987, 1991, 1995 | 5 |
| Cro-Cro | 1988, 1990, 1996, 2007 | 4 |
| Luta | 1994 (Tie), 2006 | 2 |
| Singing Sandra | 1999, 2003 | 2 |
| Sugar Aloes | 2002, 2008 | 2 |
| Roderick "Chucky" Gordon | 2014, 2015 | 2 |