Lord Invader (1943)
Roaring Lion (1945)
Lord Blakie (1954)
Mighty Spoiler (1953)
Mighty Sparrow (1956)
Folkes Brothers (1958)
Lord Kitchener (1960)
Toots and the Maytals (1964)
Mighty Sniper (1965)
Mighty Sparrow (1966)
Alton Ellis (1966)
Calypso Rose (1967)
Toots and the Maytals (1968)
U Roy (1969)
The Abyssinians (1969)
Sundar Popo (1969)
Brother Valentino (1971)
Jimmy Cliff (1972)
Mighty Shadow (1974)
Lord Shorty (1974)
Bob Marley and the Wailers (1975)
Peter Tosh (1975)
Burning Spear (1975)
Bunny Wailer (1976)
Junior Murvin (1976)
Culture (1977)
Bob Marley and the Wailers (1977)
Black Stalin (1979)
André Tanker (1980)
Bob Marley and the Wailers (1980)
Arrow (1982)
Gergory Isaacs (1982)
Dennis Brown (1984)
Wayne Smith (1985)
David Rudder (1986)
David Rudder (1987)
David Rudder and Charlie’s Roots (1988)
Brother Resistance (1987)
Ras Shorty I and the Love Circle (1989)
Mighty Chalkdust (1989)
Colin Lucas and Taxi (1991)
Richard “Nappy” Mayers (1992)
Chaka Demus and Pliers (1992)
Buju Banton (1995)
Sizzla (1997)
Beenie Man (1998)
Singing Sandra (1999)
3 Canal (1999)
Ella Andall (2000)
Sean Paul (2002)
Sidebars
10 more classic old-time calypsos
5 classic smuts
10 more Birdie classics
5 classic mentos
10 more classic Kitch songs
5 more ska classics
5 more classic rocksteady songs
9 more classic calypsos by women
5 more classic calypsos of the 60s
5 more chutney classics
4 more classic calypsos of the 1970s
5 more Jimmy Cliff songs
3 more classic Shadow songs
6 more early soca classics
10 more Bob Marley classics
10 more 70s reggae classics
5 more André Tanker songs
5 more classic calypsos of the 80s
5 80s reggae classics
5 more “small island” classics
5 more early dancehall classics
10 more David Rudder classics
3 more classic cricket calypsos
3 more classic Chalkie songs
10 more classic party songs
5 more 90s dancehall classics
5 later roots reggae classics
5 more classic calypsos of the 90s
2 classic parang tunes
2 Caribbean rock songs
3 more classic rapsos
. . .
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