Calypso Winners from 1962 to 2021

Here are the winners of Montserrat’s calypso competition from 1962 to 2021.

Year Artist Songs
1962 Justin “Hero” Cassell Lizzie and Joe
1963 Alfred “Warrior” Christopher Kennedy & Same Old Saturday Night
1964 Lorenzo “Challenger” Cassell Montserratians Be Ambitious & They Do Away With the Bald Head Man
1965 Justin “Hero” Cassell Wicked Married Men & Drive Old Man Drive
1966 Alfred “Warrior” Christopher Six-Foot Man Rat & Winston Churchill
1967 Alfred “Warrior” Christopher Lick Him Dr. Herbert & People Never Satisfy
1968 Winston “Young Warrior” Christopher Martin Luther King & 4 O’Clock In The Morning
1969 – 1971 No Calypso Competitions
1972 Justin “Hero” Cassell High Cost of Living & Rum Side
1973 Justin “Hero” Cassell Back To The Land & Long Time Christmas
1974 Alphonsus “Arrow” Cassell Montserrat English & Leggo Yourself
1975 Alphonsus “Arrow” Cassell Monique & Wind Of Change
1976 Alphonsus “Arrow” Cassell Roll Back & Change That Mentality
1977 Ishmael “Cutter” Skerritt Kai & Afro
1978 Everton “Reality” Weekes Pave The Way & Jump Up Baby
1979 Everton “Reality” Weekes Rolling Bum Bum & Save Energy
1980 Everton “Reality” Weekes Struggle & Masquerade
1981 Justin “Hero” Cassell The Flood & Don’t Mess Wid Me Country
1982 Everton “Reality” Weekes True Hero & Jumbie Dance
1983 Justin “Hero” Cassell String Band Jam & Old Time Sayings
1984 Everton “Reality” Weekes Make A Sacrifice & How You Like It
1985 Justin “Hero” Cassell Who Is De Man & Greedy Merchants
1986 Justin “Hero” Cassell Body to Body & I’m Underage
1987 Cecil “Cepeke” Lake Help Me Out & Turn Me On
1988 Earl “Hustler” Browne Don’t Mash Up The Festival & We Don’t Have to Wait
1989 Justin “Hero” Cassell Close Dem Down & Where De Galvanize
1990 Cecil “Cepeke” Lake Somebody & One More Try
1991 Kelvin “Tabu” Duberry Living In Hell & Let It Be for Better
1992 Keithroy “De Bear” Morson Back To Basics & Face The Truth
1993 Keithroy “De Bear” Morson The Time Has Come & Show Respect
1994 Roland “Kenzie” Johnson Oh Montserratians & We Need Love In The World
1995 Roland “Kenzie” Johnson Black Man & The People’s Cry
1996 Lenroy “Patriot” Tuitt Cry For Freedom & Proud Montserratian
1997 Roland “Kenzie” Johnson Shelter Life (one song only)
1998 Herman “Cupid” Francis How Many More (one song only)
1999 Cecil “Cepeke” Lake Payoff & Potholes
2000 Silvina “Kandie” Malone Vote for DFID & Rock Down de Place
2001 Earl “Hustler” Browne Solidarity & Temporary
2002 Joseph “Pops” Morris Thank You & Let’s Team Up
2003 Silvina “Kandie” Malone Change The Board & Everything is Not OK
2004 Andy Kirnon Judicial Flaws & Hand in the Air
2005 Andy Kirnon Imagine & We Flying
2006 Silvina “Kandie” Malone My Vision & Front Line
2007 Justin “Hero” Cassell The Country Need Prayer & All They Want Is Money
2008 Herman “Cupid” Francis 20/20 Cricket World & & Beyond Black & White
2009 Silvina “Kandie” Malone Pick Up The Pieces & Who Do We Blame
2010 Herman “Cupid” Francis The Tree & Before I Die
2011 Garnett “Sylk” Thompson Changing World & Never Give Up
2012 Herman “Cupid” Francis We Outsourcing & Shortly After Takeoff
2013 Baptiste Wallace Dracula System & Who Will It Be
2014 Keithroy “De Bear” Morson Don’t Forget Your Juliet & Got To Go
2015 Steve “Iceman” Weekes Nar Sell Out & 20 Years On
2016 Kevin “King Natty” Farrell Bad Mind & Big Up To Funky Man
2017 Kenneth “Rabo” Silcott The Promise & Brother’s Cry
2018 Garnett “Sylk” Thompson Trade War & All Hands on Deck
2019 Steve “Iceman” Weekes Agent of Change & Daddy I Cry to You
2020 Keithroy “De Voice” Morson Call Daddy & By Faith
2021 Keithroy “De Voice” Morson Let us Rebuild & Don’t Wake the Bear