Trinidad's Calypso Music | Monarchs & Road March Winners

 Photo © Bear Family Records

Calypso music was the driving force for Carnivals in Trinidad and Tobago (Soca music now has that honor). Trinidad and Tobago is credited with the 'origin' and evolution of Calypso music as we know it today.

“Iron Duke in the Land” is considered the first recorded calypso in English (recorded in 1914). Earlier calypsos were sung in patois. “Iron Duke in the Land” is a calypso by Henry Julian (a.k.a. Julian Whiterose) in which he boasts about roles he portrayed in the White Rose Social Union (his masquerade band) in the 1890s when he was instrumental in developing fancy masquerade bands.

During that period the musical style was called Cariso. The term “Calypso” evolved later at the turn of the nineteenth century. This title “Iron Duke in the Land,” is the only title of Whiterose’s recordings known to exist. Julian also performed under the names J. White Rose, Henry Julian, and J. Resigna.

Credit: TUCO

"The Real Calypso" is the story of Calypso that was birthed on the island of Trinidad during the formative years of the colony. This page should help with some of the facts that you should know about Trinidad and Tobago's Calypso music!

We continue to read about how the art form of calypso developed over the years. Trinidad and Tobago is a very unique society and many have tried to take away from our accomplishments. However, the truth can be found in many recorded  historical data which can and will be disputed but never refuted. 

"In many islands of the Caribbean, there are calypso-like songs -- e. g., the shanto of British Guiana, the plena of Puerto Rico, and the mento of Jamaica -- but the calypso of Trinidad and Tobago, called cariso by Atilla (Raymond Quevedo), stands apart on its own because of characteristics peculiar to itself. Among these traits are: the "halftone" (strong syncopation) in its rhythmic system, the topicality, its tendency to satirize upon every conceivable subject, its allusion and open picong, and its double entendre."

Link:Folkways Records/media.smithsomianfolkways.org.

If you want to know the real story then go to the link below to learn about "The Real Calypso". The link takes you to to the Smithsonialfolkways.org webpage for a very informative and revealing read. The story begins in Trinidad and that is something that many individuals are attempting to distort with stories about Calypso 'erupting all over the Caribbean region during the days of slavery. Obviously they have confused folk songs with the style that became known as Calypso!

I have posted some of the dates of interest for Trinidad's Calypso music. Just take a look at the dates below (Did you know the following) with special reference to the facts presented about the first instrumental and first vocal recordings of calypso. These are important dates and, I am certain, you will appreciate the fact that Trinidad is really "the well" from which calypso sprung and blossomed to what it is today. 

This blog has presented a list of calypso monarch winners and additionally, we add another important lists - Leggos and Road March winners. In continuing with the presentation of historical data we list the winners of the famous 'Road March Competition' as it relates to Trinidad and Tobago for what was known as 'Leggos' and now called 'Road March' (officially from 1962).

Did you know the following:

• Calypsos were first sung in French Creole then a mix of Patois and English
• The Rhythm of Calypso  (beat) is done in 2/4, 4/4 time (see "Meter" at  this link for an explanation of Rhythm (beats in the music)
• First ever Calypso instrumental recording was done in 1912 by Lovey's Orchestra.
• First ever vocal Calypso recording was made in 1914 when the "Duke of Iron" teamed up with Jules Sims.
• First ever Calypso tent opened in Port-of-Spain in 1921 was the "Railway Douglas Tent".
• First ever female to sing in a calypso tent was "Lady Trinidad" in 1935.
• First ever female Calypsonian to cut a record was "Lady Trinidad" in 1937.
• First ever "Young Brigade Tent" opened in 1947 by 24 year-old Lord Kitchener, featuring Lord Melody, Mighty Spoiler, Mighty Viking. 

Some of the facts above were sourced from Trinicenter.com at this LINK

Calypso Monarch Competition Winners

If you always wanted to have a list of the Calypso Monarchs of Trinidad and Tobago and had difficulty locating the information then help is here!  If anyone has information to add to list please leave a comment or send an email to ananda2456@gmail.com. The record shows that Sparrow won the crown eight (8) times but from 2017 Chalkdust took the lead with his ninth win. In third place is  Stalin with 5 victories, Duke and Cro Cro with 4, Lord Melody  with 3 victories, Atilla the Hun, Striker, Spoiler, Singing Sandra, Sugar Aloes and Luta and Roderick "Chucky" Gordon with 2 wins each. Then we have the rest with one victory each.

Sparrow (8 wins): 1956, 1960, 1962, 1963, 1972, 1973, 1974 and 1992

Chalkdust (9 wins): 1976, 1977, 1981, 1989, 1993, 2004, 2005, 2009 & 2017

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). 

1939 - Growling Tiger - Trade Union (The Labour Situation in Trinidad And Tobago)

1940 - Roaring Lion  (Rise And Fall Of The British Empire)

1941 - Mighty Destroyer (Adolf Hitler)

1942 - No Carnival No Carnival

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/Cant 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 - Bomber (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

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

_________________________________________________________________________________

Top 100 Calypsos of the 20th Century
Rank|Tune & Singer

1. Progress - King Austin (Austin Lewis) 1980
2. Portrait of Trinidad - Mighty Sniper (Mervyn Hodge) 1965
3. Jean and Dinah - Mighty Sparrow (Slinger Francisco) 1956
4. Bassman - Mighty Shadow (Winston Bailey) 1974
5. Fire in Your Wire - Calypso Rose (McArthur Lewis) 1967
6. High Mas - David Rudder (David Rudder) 1998
7. Dan is the Man - Mighty Sparrow (Slinger Francisco) 1963
8. Maria - Lord Blakie (Carlton Joseph) 1962
9. If the Priest Could Play - Mighty Cypher (Dillary B Scott) 1967
10. The Sinking Ship - Gypsy (Winston Peters) 1986
11. Jahaji Bhai - Brother Marvin (Selwyn Demming) 1996
12. God Bless Our Nation - Lord Baker (Kent King) 1967
13. Rainorama - Lord Kitchener (Aldwyn Roberts) 1973
14. Steel Band Clash - Lord Blakie (Carlton Joseph) 1954
15. The Road - Lord Kitchener (Aldwyn Roberts) 1963
16. Yankee Dollar (Rum and Coca Cola) - Lord Invader (Rupert Grant) 1946
17. Mama Look A Boo Boo - Lord Melody (Fitzroy Alexander) 1956
18.  Lazy Man - Mighty Dougla (Clatis Ali) 1961
19. Caribbean Unity - Black Stalin (Leroy Calliste) 1979
20. The Slave - Mighty Sparrow (Slinger Francisco) 1963
21. Child Training - Mighty Composer (Fred Mitchell) 1969
22. Love in the Cemetery - Lord Kitchener (Aldwyn Roberts) 1963
23. Matilda - King Radio (Norman Span) 1938
24. Little Black Boy - Gypsy (Winston Peters) 1997
25. Federation - Mighty Sparrow (Slinger Francisco) 1962
26. Burn Dem - Black Stalin (Leroy Calliste) 1987
27. Ice Man (aka Ice Ice) - Lord Melody (Fitzroy Alexander) 1960
28. Rich Man Poor Man - Lord Brynner (Kade Simon) 1960
29. Um Ba Yao - Merchant (Dennis F. Williams) 1978
30. La La - Lord Nelson (Robert Nelson) 1976
31. Nature's Plan - Johnny King (Johnston King) 1984
32.  Poverty is Hell - Shadow (Winston Bailey) 1994
33. The Will - Scrunter (Owen Reyes Johnson) 1982
34. Tourist Leggo - Short Shirt ( Emmanuel McLean ) 1976/7
35. Trouble in Arima - Lord Kitchener (Aldwyn Roberts) 1954
36. Ten to One is Murder - Mighty Sparrow (Slinger Francisco) 1960
37. Lorraine - Explainer (Winston Henry) 1982
38. Ganges and the Nile - David Rudder (David Rudder) 1999
39. Come Leh We Go Sookie - King Fighter (Shurland Wilson) 1964
40. Dustbin Cover - Crazy (Edwin Ayoung) 1978
41. Joan and James (aka Five Little Popos) - Mighty Bomber (Clifton Ryan) 1964
42. Life is A Stage - Brother Valentino (Emrold Phillips) 1972
43.  Mama Dis is Mas - Lord Kitchener (Aldwyn Roberts) 1964
44. Pan Talent - Mighty Terror (Fitzgerald Henry) 1965
45. For Cane - Gypsy (Winston Peters) 1972
46. Mary Anne - Roaring Lion (Raphael De Leon) 1946
47. Severe Licking - Baron (Timothy Watkins) 1971
48. Watch Out My Children - Ras Shorty I (Garfield Blackman) 1989
49. Split Me in Two - Mighty Dougla (Clatis Ali) 1961
50. Ras Mas - Explainer (Winston Henry) 1981
51. My Pussin - Lord Kitchener (Aldwyn Roberts) 1965
52. Mama Popo - Brigo (Samuel Abraham) 1960s?
53. Black is Beautiful - Duke (Kelvin Pope) 1969
54. Money is King - Growling Tiger (Neville Marcano) 1935
55. Juba Dubai - Chalkdust (Hollis Liverpool) 1977
56. A Mother's Love - Destroyer (Donald Glasgow) 1941
57. Too Much Man Family - Mighty Zandolie (Sylvester Anthony) 1967
58. King Liar - Lord Nelson (Robert Nelson) 1977
59. Melda (Obeah Wedding) - Mighty Sparrow (Slinger Francisco) 1966
60. The Mecca - Brother Mudada (Alan Fortune) 1987
61. Mr. Walker - Mighty Sparrow (Slinger Francisco) 1968
62. The Bedbug - Mighty Spoiler (Theophilus Phillip) 1953
63. Congo Man - Mighty Sparrow (Slinger Francisco) 1965/1989
64. Pan in A Minor - Lord Kitchener (Aldwyn Roberts) 1987
65. Education - Mighty Sparrow (Slinger Francisco) 1967
66. People Will Talk - King Fighter (Shurland Wilson) 1962
67. Flag Woman - Lord Kitchener (Aldwyn Roberts) 1976
68. Gavaskar - Relator (Willard Harris) 1972
69. Soca Baptist - Blueboy ( Austin Lyons ) 1980
70. Steel and Brass - King Wellington (Wellington Quashi) 1973
71. Norman - Merchant (Dennis F. Williams) 1978
72. Indrani - Lord Shorty (Garfield Blackman) 1972
73. Never Ever Worry - Lord Pretender (Alric Farrell) 1962
74. Is Thunder - Duke (Kelvin Pope) 1987
75. Run the Gunslingers - Lord Caruso (Emmanuel Pierre) 1959
76. Papa Chunks - Roaring Lion (Raphael De Leon) 1941/1995
77. Scrunting Calypsonian - Trinidad Rio (Daniel Brown) 1978
78. Supposing - Mighty Composer (Fred Mitchell) 1964
79. Pan in Danger - Merchant (Dennis F. Williams) 1985
80. The Bionic Man - Maestro (Cecil Hume) 1977
81. What is Calypso? - Mighty Duke (Kelvin Pope) 1968
82. Voices From the Ghetto - Singing Sandra (Sandra De Vignes) 1999
83. The Graf Zeppelin - Atilla the Hun (Raymond Quevedo) 1934
84. The Five Rules of Calypso - Mighty Fearless (Mikey Hamit) 1966
85. Santa - King Solomon (Samuel Ryan) 1961
86. Miss Tourist - Lord Kitchener (Aldwyn Roberts) 1968
87. The Outcast - Mighty Sparrow (Slinger Francisco) 1963
88. Women and Money - Mighty Conqueror (Leroy Paul) 1962
89. Brown Skin Girl - King Radio (Norman Span) 1933
90. Die with My Dignity - Singing Sandra (Sandra De Vignes) 1987
91. Black Man Come to Party - Black Stalin (Leroy Calliste) 1991
92. Ma and Pa - Lord Creator (Kenrick Patrick) 1965
93. Obey the Highway Code - Magic (A. Rampersad) 1960s?
94. Never Hang Your Hat - Lord Cristo (Christopher Laidlow) 1967
95. Chinese Children - Mighty Terror (Fitzgerald Henry) 1950
96. May May - Mighty Sparrow (Slinger Francisco) 1960
97. Raycan - Lord Shortshirt (Hector Emmanuel) 1977
98. Soul Chick - Funny (Donric Williamson) 1973
99. Don't Interfere - The Hawk (Kenneth Haywood) 1961
100. Woman on the Bass - Scrunter (Owen Reyes Johnson) 1980

_________________________________________________________________________________

Trinidad's Most Popular Leggos (Before 1962) & Road March Winners (From 1962)

The following post is a reprint from the Blog Santiwah. Some of the dates in the post date to an earlier period in the history of the Road March competition. The winning songs played by the bands from 1932 up until 1961 were called "Leggos" (Break Away). From 1962 the competition became 'officially entrenched' in the Carnival scene and was given the name "Road March"(current name). 

The real names of the Calypsonians here were sourced from TUCO and added to this listing to ensure 'full disclosure' with the listing. Thanks to TUCO and their research for listing the official names of the singers. The names were added here as a public service!

From 1932 to 1961 there was no official Road March Competition! The official competition was sanctioned in 1962! The video at the end of this listing was sourced from YouTube and is presented for your listening pleasure by "IsDePanInMe". You can now listen to a selection of these winning calypsos!

The Early Years
1834 Congo Barra - Point De Six Ans (No Six Years)
1835 to 1896 - No Information (pending)
1897 Chantwell - J'ouvert Band
1898 No Information (pending)
1899 Chantwell - Prisonie Levez
1900 to 1905 - No Information (pending)
1906 Sophie Mataloney aka Jamette Matador - Pauline
1907 Lionel Belasco - L'Annee Passee (last year); (melody used by Lord Invader in 1943 hit 'Rum and Coca Cola')
1911 Lionel Belasco - Poeme One
1915 - 1918 World War 1 - No Carnival
1919 (Information pending)
1920 Atilla The Hun - Bigman Sweetman
1921 Johnny Walker - Go Way Gal
1922 Atilla The Hun - Toddy
1923 King Houdini - Sly Mongoose
1924 (Name of Singer pending) - Mavis Powder

1925 King Houdini - Fire Brigade Water The Road
1926 Sam Manning - Camilla
1927 Atilla The Hun - Song pending (information needed)
1928 Mentor - Mr. Huggins
1929 Pending (information needed)
1930 Inveigler - Captain Cipriani
1931 King Houdini - Mr. Huggins (remake)

The Leggo Years

1932 Norman Spann aka King Radio  Tiger Tom Play Tiger Cat

1933 Norman Spann aka King Radio  Wash Pan Wash
1934 Cletus Ali aka Dougla  After Johnny Drink Me Rum
1935 Rafael Cairi Llama De Leon aka Roaring Lion  Dingolay Oy
1936 Rafael Cairi Llama De Leon aka Roaring Lion  Advantage Could Never Done
1937 Rafael Cairi Llama De Leon aka Roaring Lion  Netty Netty
1938 Rafael Cairi Llama De Leon aka Roaring Lion  No Norah Darling
1939 Norman Spann aka King Radio  Mathilda
1940 Egbert Moore aka Beginner  Run Yuh Run
1941 Rafael Cairi Llama De Leon aka Roaring Lion  Whoopsin, Whoopsin

1942  No Carnival No Carnival

1943  No Carnival No Carnival

1944  No Carnival No Carnival

1945  No Carnival No Carnival

1946  Aldwyn Roberts aka Lord Kitchener  - Jump In The Line or Chinese Never Had A VJ Day (Lai Fook Lee)/Unofficial Leggo for that year (information  is confusing regarding which song actually won)Lee))/Unofficial Road March!
1947  Andrew Bernard aka King Pharoah  King Pharoah
1948  Fitzroy Alexander aka Lord Melody  Canaan Barrow
1949  Victor Atwell aka Wonder  Ramgoat Baptism
1950  Cephas Alexander aka Killer  In a Calabash
1951  Fitzgerald Henry aka Terror  Tiny Davis
1952  Carlton Gomes aka Spit Fire  Post Post
1953  Carlton Gomes aka Spit Fire  Bow Wow Wow
1954  Carlton Joseph aka Blakie  Steel Band Clash
1955  German Composition made popular by BBC radio UK 1953/1954 Happy Wonderer (Valerie Valera)
1956  Slinger Francisco aka "The Mighty Sparrow"  Jean and Dinah
1957  Carlton Gomes aka Spitfire PNM
1958  Slinger Francisco aka "The Mighty Sparrow"  Pay As You Earn
1959  Caruso  Run the Gunslingers
1960  Slinger Francisco aka "The Mighty Sparrow"  Mae Mae
1961  Slinger Francisco aka "The Mighty Sparrow"  Royal Jail

The Road March Years
1962  Blakie  Maria (This song was the 'First official Road March Winner')
1963  Aldwyn Roberts aka Lord Kitchener  The Road
1964  Aldwyn Roberts aka Lord Kitchener  This Is Mas
1965  Aldwyn Roberts aka Lord Kitchener  My Pussin
1966  Slinger Francisco aka "The Mighty Sparrow"  Obeah Wedding
1967  Aldwyn Roberts aka Lord Kitchener  Sixty Seven
1968  Aldwyn Roberts aka Lord Kitchener  Miss Tourist
1969  Slinger Francisco aka "The Mighty Sparrow"  Sa Sa Yae
1970  Aldwyn Roberts aka Lord Kitchener  Margie
1971  Aldwyn Roberts aka Lord Kitchener  Madison Square
1972  Slinger Francisco aka "The Mighty Sparrow"  Drunk and Disorderly
1973  Aldwyn Roberts aka Lord Kitchener  Rainorama
1974  Winston Bailey aka "Shadow"  Bass Man
1975  Aldwyn Roberts aka Lord Kitchener  Tribute to Spree Simon
1976  Aldwyn Roberts aka Lord Kitchener  Flag Woman
1977  McArthur Lewis aka Calypso Rose  Tempo
1978  McArthur Lewis aka Calypso Rose   Come Leh We Jam (Soca Jam)
1979  Sylvester Lockhart aka Poser  Ah Tell She
1980  Austin Lyons aka Blue Boy/Super Blue  Soca Baptist
1981  Austin Lyons aka Blue Boy/Super Blue  Ethel
1982  Seadley Joseph akaPenguin  Deputy
1983  Austin Lyons aka Blue Boy/Super Blue  Rebecca
1984  Slinger Francisco aka "The Mighty Sparrow"  Doh Back Back
1985  Edwin Ayoung aka Crazy   Soucoyant
1986  David Rudder  Bahia Girl
1987  Kelvin Pope aka Duke  Thunder
1988  Christopher Herbert aka Tambu  This Party Is It
1989  Christopher Herbert aka Tambu  Free Up
1990  Christopher Herbert aka Tambu  We Ain?t Going Home
1991  Austin Lyons aka Blue Boy/Super Blue  Get Something and Wave
1992  Austin Lyons aka Blue Boy/Super Blue  Jab Jab
1993  Austin Lyons aka Blue Boy/Super Blue  Bacchanal Time
1994  Barnett Henry aka Preacher  Jump and Wave
1995  Austin Lyons aka Blue Boy/Super Blue  Signal To Lara
1996  Nigel Lewis  Movin
1997  Machel Montano  Big Truck
1998  Wayne Rodriguez  Footsteps
1999  Sanell Dempster  River
2000  Austin Lyons aka Blue Boy/Super Blue| Neil Iwer George (Tie) Pump Up|Carnival Come Back Again
2001  Winston Bailey aka Shadow  Stranger
2002  Naya George  Trinidad
2003  Faye-Ann Lyons  Display
2004  Shurwayne Winchester  De Band Coming
2005  Shurwayne Winchester  Dead or Alive
2006  Machel Montano and Patrice Roberts  Band of the Year
2007  Machel Montano  Jumbie
2008  Faye Ann Lyons Alvarez  Get on
2009  Faye Ann Lyons Alvarez  "Meet Super Blue"
2010  JW and Blaze Palance
The listed information was sourced from various Internet sites (and my limited knowledge) with the bulk of the list coming from www.westindianculture.com.
2011 - Machel Montano HD - Advantage
2012 - Machel Montano - Pump Yuh Flag
2013 - Austin Lyons aka Blue Boy/Super Blue - Fantastic Friday
2014 - Machel Montano HD - MOR (Ministry of Road)
2015 - Machel "Monk Monte" Montano - Like Ah Boss
2016 - Machel Montano - Waiting on the Stage
2017 - Ultimate Rejects ft. MX Prime - Full Extreme

2018 - Machel Montano & Austin "Superblue" Lyons - Soca Kingdom

2019 - Machel Montano, Ian Alvarez (Bunji Garlin) & Gamal Doyle (Skinny Fabulous) - Famalay