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: 2026-03-14
1.
Day-O (The Banana Boat Song)
Harry Belafonte
May 18, 1956
2.
Jump In the Line
Harry Belafonte
July 21, 1961
3.
Jamaica Farewell
Harry Belafonte
January 1, 1956
4.
Mr. Walker
The Mighty Sparrow
May 13, 2011
5.
Theme from Dr. Zhivago
Byron Lee & The Mighty Sparrow
October 3, 1998
6.
We Are Back (feat. Beto Perez & Braveboy)
Max Pizzolante
January 30, 2026
7.
Take Me Home
Freetown Collective
November 28, 2024
8.
Island In the Sun
Harry Belafonte
January 1, 1957
9.
Suriname
The Young Ones of Guyana
June 21, 2019
10.
Island In the Sun
Jamaican Steel Band
January 1, 2001
11.
Man Smart (Woman Smarter)
Harry Belafonte
May 18, 1956
12.
Wanted Dead or Alive
The Mighty Sparrow
November 6, 2001
13.
The Jack-Ass Song
Harry Belafonte
May 18, 1956
14.
(Day-O) The Banana Boat Song (Cover Version)
Geek Music
June 2, 2021
15.
Hot, Hot, Hot!
Jamaican Steel Band
January 1, 2001
16.
The Banana Boat Song (Day-O)
Jamaican Steel Band
January 1, 2001
17.
Guantanamera
Jamaican Steel Band
January 1, 2001
18.
Fire in Guadalupe
Los Lores
October 15, 1991
19.
Tesa party
Lord Kontiki & Lord Kontiki & Panaswing
October 15, 1991
20.
Red, Red Wine
Jamaican Steel Band
January 1, 2001
21.
Come Back Liza
Harry Belafonte
January 1, 1900
22.
I Do Adore Her
Harry Belafonte
January 1, 1900
23.
Brown Skin Girl
Harry Belafonte
May 18, 1956
24.
Jamaica Farewell
Jamaican Steel Band
January 1, 2001
25.
Booboo Man (Mama, Look At Bubu)
Lord Melody
September 26, 2000
26.
Will His Love Be Like His Rum?
Harry Belafonte
May 18, 1956
27.
Star-O
Harry Belafonte
May 18, 1956
28.
Indian Party
Lord Christo
November 12, 2021
29.
Birth of Ghana (feat. Freddy Grant´s Caribean Rhythm)
