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: 2026-05-14
1.
Day-O (The Banana Boat Song)
Harry Belafonte
May 18, 1956
2.
Jamaica Farewell
Harry Belafonte
January 1, 1956
3.
Hot, Hot, Hot!
Jamaican Steel Band
January 1, 2001
4.
Jump In the Line
Harry Belafonte
July 21, 1961
5.
Angelina
Harry Belafonte
July 21, 1961
6.
Star-O
Harry Belafonte
May 18, 1956
7.
Island In the Sun
Harry Belafonte
January 1, 1957
8.
Red, Red Wine
Jamaican Steel Band
January 1, 2001
9.
The Banana Boat Song (Day-O)
Jamaican Steel Band
January 1, 2001
10.
Man Smart (Woman Smarter)
Harry Belafonte
May 18, 1956
11.
Cocoanut Woman
Harry Belafonte
January 27, 1957
12.
Dr Cassandra
Gabby
October 9, 2001
13.
Sweetheart from Venezuela
Harry Belafonte
July 21, 1961
14.
Will His Love Be Like His Rum?
Harry Belafonte
May 18, 1956
15.
Volcano
Jamaican Steel Band
January 1, 2001
16.
Take Me Home
Freetown Collective
November 28, 2024
17.
I Do Adore Her
Harry Belafonte
January 1, 1900
18.
Burn Dem
Black Stalin
January 1, 1991
19.
Jamaica Farewell
Jamaican Steel Band
January 1, 2001
20.
Ogun
Clive Zanda
November 10, 2017
21.
Sweet Spice in the Air (feat. Calypso Band) [Calypso Mix]
![Sweet Spice in the Air (feat. Calypso Band) [Calypso Mix] song art](https://is1-ssl.mzstatic.com/image/thumb/Music221/v4/57/a8/30/57a8306d-2f0a-c095-17fc-41e148a34e41/d3f62750-3f04-4eb3-82c4-931b7ba876ad.jpg/170x170bb.png)
