Calypso Monarch Competition Winners of Trinidad & Tobago

Image via Bing images © NCC/TUCO/Terri Lyons
The Calypso Monarchs of Trinidad and Tobago are legendary figures in the world of calypso music. Calypso is a unique musical genre that originated in Trinidad and Tobago and has since spread to other parts of the Caribbean and the world. Calypso music is characterized by its lively rhythms and witty lyrics, often used to express social and political commentary.

The Calypso Monarch competition is held annually during the Carnival season in Trinidad and Tobago, and it is considered one of the most prestigious events in the calypso world. The competition has been held since 1939 and has attracted some of the most talented calypsonians in the country.

Over the years, many legendary artists have won the Calypso Monarch title, including The Mighty Chalkdust, The Mighty Sparrow and Black Stalin. These artists are not only famous in Trinidad and Tobago but have also gained international recognition for their contributions to calypso music.

The Calypso Monarch competition continues to be a significant event in Trinidad and Tobago's cultural calendar. It provides a platform for artists to showcase their talents and express their views on social and political issues. The competition also helps to keep the traditions of calypso music alive and thriving, ensuring that future generations can enjoy this unique and vibrant art form.

So many of us are consumed with "who won the most titles" and who is the best. The second part is subjective but the person with the most wins will eventually have the bragging rights to most prolific winner. So, let's get to the actual record. A review of the results over the years shows that Slinger Francisco aka 'The Mighty Sparrow", won the crown eight (8) times but he did not win the most titles!  That honor goes to Hollis Urban Lester Liverpool aka "The Mighty Chalkdust". From 2017, Chalkdust took the lead with his ninth win. In third place is Leroy Calliste aka "Black Stalin" with five victories. The list of winners continues with Kelvin "Mighty Duke" Pope and Winston "Cro Cro" Rawlins with 4, Lord Melody (Fitzroy Alexander) with 3 victories, Atilla the Hun (Raymond Quevado), Mighty Striker (Percival Oblington), Mighty Spoiler (Theophilus Philip), Singing Sandra (Sandra DeVignes-Millington), Sugar Aloes (Michael Osuna), Luta (Morell Peters) and Roderick "Chucky" Gordon with 2 wins each. Then we have the rest with one victory each.
  • Mighty Sparrow (8 wins): 1956, 1960, 1962, 1963, 1972, 1973, 1974 & 1992
  • Mighty Chalkdust (9 wins): 1976, 1977, 1981, 1989, 1993, 2004, 2005, 2009 & 2017
  • Black Stalin (5 wins): 1979, 1985, 1987, 1991, & 1995
Please check the list for the information that you desire - it is an interesting list but please note that the first year listed is 1939. If anyone has information about the start of this competition, I would be happy to post it on this blog. Apparently, 1939 is the first year of the Calypso Monarch Competition and the Growling Tiger (Neville Marcano) won the competition with a song entitled "The Labour Situation in Trinidad And Tobago.(Wikipedia). 

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1939 - Growling Tiger - Trade Union (The Labour Situation in Trinidad and Tobago). He was awarded the first prize purse of $20.00.

1940 - Roaring Lion (Rise and Fall Of the British Empire)
1941 - Mighty Destroyer (Adolf Hitler)
1942 - No Carnival, No Carnival (Daily Mail Report)
1943 - No Carnival, No Carnival
1944 - No Carnival, No Carnival
1945 - No Carnival, No Carnival
1946 - Attila The Hun (Mail Report)
1947 - Attila The Hun (Million Dollar Jail)
1948 - Mighty Spoiler (Royal Wedding)
1949 - Lord Melody (Glory Mama Glory)

1950 - No Competition
1951 - Lord Melody (Jonah and The Bake)
1952 - No Competition
1953 - Spoiler (Bed Bug) 
1954 - Melody (Second Spring)
1955 - Spoiler (Pick Sense Out of Nonsense)
1956 - Sparrow (Jean and Dinah)
1957 - Pretender (Que Sera Sera)
1958 - Striker (Don't Blame the PNM/Can't Find A Job To Suit Me)
1959 - Striker (Ban the Hoola Hoop/Comparison)

1960 - Sparrow (Ten to One is Murder/Mae Mae)
1961 - Dougla (Lazy Man/Split Me in Two)
1962 - Sparrow (Sparrow Come Back Home/Federation)
1963 - Sparrow (Dan is the Man/Kennedy)
1964 - Mighty Bomber (Clifton Ryan) - (Joan and James/Bomber's Dream)
1965 - Sniper (Portrait of Trinidad/More Production)
1966 - Terror (Pan Jamboree/Last Year's Happiness)
1967 - Cypher (Last Elections/If the Priest Could Play)
1968 - Duke (What is Calypso/Social Bacchanal)
1969 - Duke (Black is Beautiful/One Foot Visina)
1970 - Duke (Brotherhood of Man/See-Through)
1971 - Duke (Mathematical Formula/Melvine & Yvonne)
1972 - Sparrow (Drunk and Disorderly/Rope)
1973 - Sparrow (School Days/Same Time, Same Place)
1974 - Sparrow (We Pass That Stage/Miss Mary)
1975 - Kitchener (Tribute to Spree Simon/Fever)
1976 - Chalkdust (Three Blind Mice/Ah Put on Meh Guns Again)
1977 - Chalkdust (Juba Dubai/Shango Vision)
1978 - Calypso Rose (Her Majesty/I Thank Thee)
1979 - Black Stalin (Caribbean Unity/Play One)

1980 - Relator (Food Prices/Take a Rest)
1981 - Chalkdust (Ah Can't Make/Things That Worry Me)
1982 - Scrunter (Lick-e-Thing/The Will)
1983 - Crusoe (Don't Cry Now/South Africa)
1984 - Penguin (We Living in Jail/Soft Man)
1985 - Black Stalin (Isms Schisms/Wait Dorothy)
1986 - David Rudder (The Hammer/Bahia Girl)
1987 - Black Stalin (Mr. Pan Maker/Burn Dem)
1988 - Cro Cro (Three Bo Rats/Corruption in Common Entrance)
1989 - Chalkdust (Chauffeur Wanted/Carnival is The Answer)

1990 - Cro Cro (Political Dictionary/Party)
1991 - Black Stalin (Bright Side/Ah Feeling to Party)
1992 - Sparrow (Both of Them/Survival or Man will survive) (second song correction by Jeron Josep)
1993 - Chalkdust (Kaiso in de Hospital/Misconceptions)
1994 - Luta; Delamo (tie) (Good Driving, Licensed Firearm / Trinity Is Meh Name,
            Not Going Down D'Road)
1995 - Black Stalin (In Times/Sundar Popo)
1996 - Cro Cro (Dey Look for Dat/Support Commentary Calypso)
1997 - Gypsy (Little Black Boy/Rhythm of the Nation)
1998 - Mystic Prowler (Look Beneath The Surface/Vision of TnT in the Year 2010)
1999 - Singing Sandra (Song for Healing/Voices From The Ghetto)

2000 - Shadow (What's Wrong With Me/Scratch Meh Back)
2001 - Denyse Plummer (Nah Leaving/Heroes)
2002 - Sugar Aloes (Contribution, Jubilation) 
2003 - Singing Sandra (Who The Bell Tolls, Ancient Rhythms)
2004 - Dr. Hollis Liverpool aka Chalkdust (Cro Cro for Sale, Trinidad in Cemetary)
2005 - Dr. Hollis Liverpool aka Chalkdust (I in Town Too Long, Ah Doh Rhyme)
2006 - Luta (Check The Foundation, Kaiso Kaiso)
2007 - Cro Cro (Nobody Eh Go Know)
2008 - Sugar Aloes (Reflections)
2009 - Dr. Hollis Liverpool aka Chalkdust (Ah Not In Dat)

2010 - Kurt Allen (Too Bright)
2011 - Karen Asche (Be Careful What Yuh Ask For & Uncle Jack)
2012 - Duane O'Connor - The Hunt is On, Long Live Calypso
2013 - Eric Taylar (Pink Panther) - Travel Woes, Crying In The Chapel
2014 - Roderick "Chucky" Gordon - Wey Yuh Think; Wedding of the Century (Shaddi)
2015 - Roderick "Chucky" Gordon - Song #1. The Rose; Song #2. I Believe
2016 - Devon Seale - Song #1 Respect God's Voice. Song #2 The Spirit of Carnival
2017 - Dr. Hollis Liverpool aka Chalkdust - Learn From Arithmetic
2018 - Helon Francis - Change
2019 - Ronaldo London - Man's Imagination

2020 - Terri Lyons - Song #1 Meghan, My Dear & Song #2 Obeah
2021 - No Carnival/No Competition due to the World Covid-19 Pandemic
2022 - No Carnival/No Competition due to the World Covid-19 Pandemic
2023 - Duane Ta'zyah O’Connor – Sing Hallelujah
2024 - Machel Montano - Soul of Calypso

Information for this post was obtained from several sites including Wikipedia, Toronto Lime, and Island Mix up to and including 2009.

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