| By Popularity
| Alphabetical (What's This?)|
- Belafonte, Harry (10)
- Cyril Paul and the Calypso Monarchs
Offering calypso and other Caribbean music, including rumba, bolero, cha-cha, and reggae, at a variety of venues in the Twin Cities.
- Johnny Russler & the Beach Bum Band
Bringing the sweet sound of Caribbean rock reggae & calypso.
- Kobo Town
Toronto-based group whose music draws its inspiration from traditional calypso, roots reggae, and dub poetry.
- Lord Kitchener (1922-2000)
- Mighty Sparrow, The
Calypso singer also known as Slinger Francisco, "The Birdie".