iTunes Top 40 Calypso Songs Chart

The Top Calypso Music Songs on iTunes This Week

The iTunes Top 40 Calypso Songs Chart is your weekly window into the world of calypso music — the witty, rhythm-driven music of Trinidad & Tobago — equal parts political commentary, social observation, and pure dancefloor joy. Updated every week, this chart ranks the top 40 calypso music singles on iTunes, giving you a real-time snapshot of what’s resonating most with fans of the genre right now.

The genre has been shaped by visionaries like Harry Belafonte, Lord Kitchener, and Mighty Sparrow who made calypso the voice of Caribbean culture for the world, whose work defines what calypso music can sound and feel like. Whether the genre has centuries of tradition behind it or only emerged in recent decades, the artists on this chart are its current standard-bearers.

Discover what calypso music sounds like today by exploring the full iTunes Top 40 Calypso Music Songs Chart, updated fresh this week, in the chart below.

Chart updated this week on: 2026-06-20

1.
Day-O (The Banana Boat Song) song art
Day-O (The Banana Boat Song)
Harry Belafonte
May 18, 1956

2.
Hot, Hot, Hot! song art
Hot, Hot, Hot!
Jamaican Steel Band
January 1, 2001

3.
Red, Red Wine song art
Red, Red Wine
Jamaican Steel Band
January 1, 2001

4.
Jump In the Line song art
Jump In the Line
Harry Belafonte
July 21, 1961

5.
Take Me Home song art
Take Me Home
Freetown Collective
November 28, 2024

6.
Jamaica Farewell song art
Jamaica Farewell
Harry Belafonte
January 1, 1956

7.
Bassman song art
Bassman
Shadow
June 28, 2009

8.
Lewwe Go song art
Lewwe Go
Jab King
May 29, 2026

9.
Man Smart (Woman Smarter) song art
Man Smart (Woman Smarter)
Harry Belafonte
May 18, 1956

10.
I Come Out to Play song art
I Come Out to Play
Shadow
June 28, 2009

11.
Janette song art
Janette
Shadow
June 28, 2009

12.
Don't Stop the Carnival song art
Don't Stop the Carnival
Harry Belafonte
November 1, 1971

13.
The Needle song art
The Needle
Dr. Ring Ding
January 1, 2014

14.
Angelina song art
Angelina
Harry Belafonte
July 21, 1961

15.
Cocoanut Woman song art
Cocoanut Woman
Harry Belafonte
October 24, 1966

16.
Island In the Sun song art
Island In the Sun
Harry Belafonte
January 1, 1957

17.
How You Jamming So song art
How You Jamming So
The Mighty Sparrow
January 8, 2000

18.
Monkey song art
Monkey
Harry Belafonte
July 21, 1961

19.
Come Back Liza song art
Come Back Liza
Harry Belafonte
January 1, 1900

20.
Island In the Sun song art
Island In the Sun
Jamaican Steel Band
January 1, 2001

21.
Caribbean Unity song art
Caribbean Unity
Black Stalin
January 1, 1991

22.
Kingston Town song art
Kingston Town
Jamaican Steel Band
January 1, 2001

23.
Super Soaker song art
Super Soaker
Angeleau
February 28, 2026

24.
Jack song art
Jack
Gabby
October 9, 2001

25.
Under the Sea song art
Under the Sea
Calypso Kings
June 25, 2021

26.
Listen To The Ocean song art
Listen To The Ocean
The Merrymen
March 1, 2011

27.
Freight Train song art
Freight Train
The Merrymen
January 30, 1962

28.
Jean and Dinah song art
Jean and Dinah
The Mighty Sparrow
May 13, 2011

29.
Jamaica Farewell song art
Jamaica Farewell
Jamaican Steel Band
January 1, 2001

30.
Mr. Walker song art
Mr. Walker
The Mighty Sparrow
May 13, 2011

31.
Brown Skin Girl song art
Brown Skin Girl
Harry Belafonte
May 18, 1956

32.
Star-O song art
Star-O
Harry Belafonte
May 18, 1956

33.
Guantanamera song art
Guantanamera
Jamaican Steel Band
January 1, 2001

34.
Obeah Wedding song art
Obeah Wedding
The Mighty Sparrow & Byron Lee
May 13, 2011

35.
Congo Man song art
Congo Man
The Mighty Sparrow
May 13, 2011

36.
Clandestino (feat. Calypso Rose) song art
Clandestino (feat. Calypso Rose)
Manu Chao
January 1, 1998

37.
Islands song art
Islands
Jamaican Steel Band
January 1, 2001

38.
Haiti Cherie song art
Haiti Cherie
Harry Belafonte
August 16, 1957

39.
I Do Adore Her song art
I Do Adore Her
Harry Belafonte
January 1, 1900

40.
Booboo Man (Mama, Look At Bubu) song art
Booboo Man (Mama, Look At Bubu)
Lord Melody
September 26, 2000

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