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| Alphabetical | By Popularity | | - 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.
- Mighty Sparrow, The
- Calypso singer also known as Slinger Francisco, "The Birdie".
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