The Most Famous Calypso Singer: Ranking the Legends in the Genre

Choose the singer you think is the most famous!

Author: Gregor Krambs
Updated on Apr 8, 2024 08:05
Welcome to StrawPoll, where your opinions matter and your voice is heard! Today, we invite you to dive into the mesmerizing world of Calypso music and be a part of our exciting ranking – "Who is the most famous Calypso singer?" From the enchanting rhythms to the captivating storytelling, Calypso has taken the world by storm, and now it's time to celebrate the maestros who've made it all possible. Vote for your favorite Calypso legend or suggest an unsung hero who's missing from our list. Let's embark on this melodious journey, explore the rich Calypso heritage, and together, uncover the ultimate Calypso icon! Cast your vote now and watch the rankings unfold before your eyes.

Who Is the Most Famous Calypso Singer?

  1. 1
    Harry Belafonte
    David Shankbone · CC BY 3.0
    Harry Belafonte known for popularizing Calypso music in the 1950s and 1960s with hits such as "Day-O (The Banana Boat Song)" and "Jamaica Farewell".
    Harry Belafonte in other rankings
  2. 2
    Mighty Sparrow a Trinidadian Calypso singer known for his social commentary and political satire in his music. He has won the Calypso King competition in Trinidad and Tobago multiple times.
  3. 3
    Lord Kitchener another Trinidadian Calypso singer who had a long and successful career in the genre, with hits such as "Sugar Bum Bum" and "London is the Place for Me".
  4. 4
    The Mighty Shadow a Trinidadian Calypso singer known for his distinctive voice and lyrics that often addressed social issues. His hit songs include "Bassman" and "Stranger".
  5. 5
    Calypso Rose a Tobagonian Calypso singer who has been performing since the 1950s. She has won multiple awards and is known for her empowering lyrics and energetic performances.
  6. 6
    Lord Invader a Trinidadian Calypso singer known for his wit and humor in his music, as well as his social commentary on issues such as racism and colonialism.
  7. 7
    The Mighty Chalkdust a Trinidadian Calypso singer who has won the Calypso King competition multiple times. His music often addresses social and political issues in Trinidad and Tobago.
  8. 8
    Black Stalin a Trinidadian Calypso singer who has won multiple Calypso King competitions. His music often addresses political and social issues in Trinidad and Tobago.
  9. 9
    Lord Nelson a Trinidadian Calypso singer who has had a long and successful career in the genre, with hits such as "Disco Daddy" and "Hot, Hot, Hot".
  10. 10
    David Rudder is a Trinidadian Calypso singer who has won multiple Calypso King competitions and is known for his socially conscious lyrics and fusion of Calypso with other genres such as salsa and jazz.

Missing your favorite singer?


Ranking factors for famous singer

  1. Achievements
    The number of hit songs, awards, and accolades the singer has received.
  2. Impact
    The influence the singer has had on the genre of Calypso and the music industry as a whole.
  3. Creativity
    The ability of the singer to bring something new and fresh to the music scene and to create original music.
  4. Stage Presence
    The ability of the singer to engage and captivate an audience during live performances.
  5. Longevity
    How long the singer has been in the industry and the consistent quality of their work over the years.
  6. Cultural significance
    How the singer has contributed to the expression of the culture and traditions of the Caribbean.

About this ranking

This is a community-based ranking of the most famous Calypso singer. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or Singer is missing, feel free to help improve the ranking!


  • 181 votes
  • 10 ranked items

Voting Rules

A participant may cast an up or down vote for each Singer once every 24 hours. The rank of each Singer is then calculated from the weighted sum of all up and down votes.


More information on most famous calypso singer

Calypso music originated in Trinidad and Tobago in the early 20th century and has since become a popular genre across the Caribbean and beyond. The music is characterized by its upbeat tempo, catchy melodies, and witty lyrics that often comment on social and political issues. Calypso singers are known for their ability to entertain and engage audiences with their unique style and storytelling skills. Some of the most famous Calypso singers include Mighty Sparrow, Lord Kitchener, and Harry Belafonte, who helped to popularize the genre in the United States with his hit song "Day-O (The Banana Boat Song)." Today, Calypso music continues to thrive and evolve, with new artists adding their own spin to this vibrant and beloved musical tradition.

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