20th-century Jamaican male singers

Jamaican reggae musician (1945–1981)

James Chambers, known professionally as Jimmy Cliff, was a Jamaican ska, rocksteady, reggae and soul musician. He was considered to be one of Jamaica's most celebrated musicians and was credited with helping to popularise reggae music internationally. At the time of his death, he was the 4th reggae musician to hold the Order of Merit, the highest honour granted by the Jamaican government for achievements in the arts and sciences. He was also nominated seven times for the Grammy Awards, winning twice.

Jamaican reggae singer and musician (1944–1987)

Jamaican reggae musician

Jamaican reggae producer (1936–2021)

Jamaican ska singer-songwriter (1941–2006)

Jamaican reggae singer, songwriter and percussionist (1947-2021)

Jamaican roots reggae musician

Jamaican reggae musician (1944–2025)

Jamaican American reggae musician

Jamaican musician

Jamaican reggae singer (1957–1999)

Jamaican singer

Jamaican reggae and dancehall deejay

Jamaican musician, singer and songwriter (1942–2020)

Jamaican singer

Jamaican reggae artist (1952-1980)

Jamaican musician

Jamaican musician (1949–1999)

Jamaican vocalist and songwriter

Jamaican musician (1942–2007)

Jamaican musician

Jamaican musician (1946–1984)

Jamaican-born British operatic bass-baritone

Jamaican singer

Jamaican musician (1957–1991)

Jamaican singer

Jamaican singer (1948–1973)

Jamaican singer (1947–2014)

Jamaican reggae singer

Jamaican musician

Canadian musician

Jamaican recording artist; musician and songwriter (1938–1992)

Jamaican singer

Jamaican musician

Patrick Thompson (4 March 1965 – 21 December 1993), better known as Dirtsman, was a Jamaican dancehall deejay.