The older brother of famous American film actor Geoffrey Holder, Boscoe was exposed to the piano at a very young age. He began his professional career playing music, but turned to painting and dancing as a teenager. Both his dancing interpretations and his paintings reflected the Afro-Caribbean experience, and he hosted his first art exhibition in 1937. During the 1940s, he had his own radio show "Piano Ramblings" on the Armed Forces radio station, and formed his own dance troupe, Boscoe Holder Dancers.
In 1946, he went to New York, USA, where he taught at the Katherine Dunham School and exhibited his paintings. He returned to Trinidad in 1948 but left for England in 1950 to pursue a career as a dancer. He formed the dance company Boscoe Holder and His Caribbean Dancers and appeared on British television in "Bal Creole."
He performed at popular clubs and theatres in England (London), France (Paris, Nice), Monaco (Monte Carlo), and Belgium (Ostend), where he had the privelege of performing with the renown dancer, Josephine Baker.
While based in England, he continued to develop his skills as a painter and held impromptu exhibits on his dancing tours, briefly returning to Trinidad from 1961 to 1962.
He returned home for good in 1970, made a name for himself as a painter with exhibits throughout the Caribbean, and later opened his studio at his home on Woodford Street in Woodbrook, Port-of-Spain
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