Chart updated this week on: 2024-11-01
1.
Day-O (The Banana Boat Song)
Harry Belafonte
May 18, 1956
2.
Sweetheart from Venezuela
Harry Belafonte
July 21, 1961
3.
Guantanamera
Jamaican Steel Band
January 1, 2001
4.
Jamaica Farewell
Jamaican Steel Band
January 1, 2001
5.
Red, Red Wine
Jamaican Steel Band
January 1, 2001
6.
Man Smart (Woman Smarter)
Harry Belafonte
May 18, 1956
7.
Jump In the Line
Harry Belafonte
October 24, 1966
8.
Calypsonian
Panama Brass
June 10, 1969
9.
Cindy, Oh Cindy
His Orchestra & Toto' Ruta
August 1, 1958
10.
Dr Cassandra
Gabby
October 9, 2001
11.
Jean and Dinah
The Mighty Sparrow
May 13, 2011
12.
Brown Skin Girl
Harry Belafonte
May 18, 1956
13.
The Jack-Ass Song
Harry Belafonte
May 18, 1956
14.
Mr. Walker
The Mighty Sparrow
May 13, 2011
15.
Mr. Walker
The Mighty Sparrow
June 6, 1992
16.
Rajin (Remix)
Adesh Samaroo
January 1, 2005
17.
Calypso Minor One
Bobby Benson and His Orchestra
March 31, 2009
18.
Day - O (Banana Boat Song)
Billykaren Beaufort
February 17, 2023
19.
![Young Boy (Trinidad Mix) [feat. Machel Montano] song art](https://is1-ssl.mzstatic.com/image/thumb/Music124/v4/16/c7/e1/16c7e137-afc0-37ec-a78e-1ee082635ce3/5060686504938_cover.jpg/170x170bb.png)
Young Boy (Trinidad Mix) [feat. Machel Montano]
Calypso Rose
October 4, 2019
20.
Will His Love Be Like His Rum?
Harry Belafonte
May 18, 1956
21.
Congo Man
The Mighty Sparrow
May 13, 2011
22.
Monkey
Harry Belafonte
July 21, 1961
23.
Come Back Liza
Harry Belafonte
January 1, 1900
24.
Booboo Man (Mama, Look At Bubu)
Lord Melody
September 26, 2000
25.
Star-O
Harry Belafonte
May 18, 1956
26.
The Big Bamboo
Mighty Panther
May 5, 2008
27.
Hosanna
Harry Belafonte
May 18, 1956
28.
Dolly Dawn
Harry Belafonte
May 18, 1956
29.
Feeling Hot Hot Hot
The Merrymen
January 1, 1984
30.
Picong Duel
Lord Melody & The Mighty Sparrow
January 1, 1957
31.
Burn Dem
Black Stalin
January 1, 1991
32.
Caribbean Unity
Black Stalin
January 1, 1991
33.
Madame Dracula
The Mighty Sparrow
November 22, 2019
34.
Jump and Bray Medley: Hold 'Em Joe / The Jack-Ass Song
Harry Belafonte
October 24, 1966
35.
Teresa
The Mighty Sparrow
September 26, 2000
36.
We Can Make It
Black Stalin
January 1, 1991
37.
Carnival Celebration
Small Island Pride
September 26, 2000
38.
Aloha
Jamaican Steel Band
January 1, 2001
39.
Islands
Jamaican Steel Band
January 1, 2001
40.
Saturday Night Blowout
John "Buddy" Williams Band
September 26, 2000