A look at the annual calypso monarchs since Montserrat Festival became official in 1962:
| 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 to 71 | No festival calypso shows | |
| 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 & Caribbean Integration |
| 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 competition) |
| 1998 | Herman "Cupid" Francis | How Many More (one song competition) |
| 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 | By Faith & Call Daddy |
| 2021 | Keithroy "De Voice" Morson | Let Us Rebuild & Don't Wake The Bear |
| 2022 | Keithroy "De Voice" Morson | Hard Like A Diamond & Ah Shoulda |
| 2023 | Garnett "Sylk" Thompson | What's On My Mind & Self-Determination |
| 2024 | Garnett "Sylk" Thompson | Only In Montserrat & Nature of Politricks |
Ruler won the crown many times but they never gave it to him.and I kwow why I wouldn’t say it here but every one in Montserrat knows why continue to rest in peace Ruler