Boscoe can be safely described as one of only a handful of Caribbean painters to have shaped Caribbean art in the 20th Century. But his career of 60 plus year was not only restricted to fine art. He also had a celebrated international career as a designer, dancer, choreographer and musician.
He began painting, self-taught, at the age of five, and by his seventh birthday was already displaying his musical acumen playing the piano. Enamoured of his island’s culture, he researched and learned the local dances and songs of Trinidad, and by the late nineteen-thirties he had formed a group of dancers and was producing shows depicting the music, songs and dances of Trinidad. During this period his career as an artist was well underway with several solo art exhibitions. During World War II Boscoe Holder had his own programme, Piano Ramblings, on the U.S. Armed Forces Radio Station. This was on the American military bases installed in Trinidad. The show aired every Sunday afternoon. His dance company also performed constantly at various Officers’ Clubs and U.S.O.’s, and Holder was commissioned by scores of servicemen to paint their portraits so that they could send them home to their families in America.
In 1946 Holder visited Martinique the birth place of his Grand Mother for the first time, and this inspirational sojourn broadened his vision prompting him to include the dances, songs, costumes and the people of the French West Indies in his shows and artwork. After the War Holder went for the first time to New York, teaching Caribbean dance at the Katherine Dunham School, and exhibiting paintings at the Eighth Street Galleries. Holder married Sheila Clarke in 1948 and the couple gave birth to their only son, Christian, the following year. In 1950 they travelled to London, which became their home for the next twenty years. Holder formed his group, Boscoe Holder and his Caribbean Dancers, in London, and introduced the first steel drums to England on his own television show in 1950, Bal Creole (aired on B.B.C. TV which, in those seminal days, was located at Alexandra Palace). Appearances in several cabarets, theatre clubs, television shows, and films followed. The company performed before Queen Elizabeth II at her coronation in 1953: representing the West Indies, they danced on a barge, part of the Royal Flotilla, on the Thames. The company also toured the Continent, appearing in Finland, Sweden, Belgium, France, Spain, former Czechoslovakia, Italy, Monte Carlo, and also in Egypt. For four years, beginning in 1959, Boscoe Holder produced, choreographed, and costumed the floorshow in the Candlelight Room at the Mayfair Hotel, as well as leading his own band, The Pinkerton Boys, in the same venue. He later became co-owner of a private club, the Hay Hill, in Mayfair. In 1960/61 he took three months off to return to Trinidad as the recipient of a “Scholarship in Reverse” given by the Trinidad government to Holder and writer V.S. Naipaul to entice them to return to the land of their birth. Boscoe Holder and his wife appeared for a second time before Queen Elizabeth II at a Command Performance at Windsor Castle in 1955. In 1966 they were among the eighteen persons invited to dine with the Queen and Prince Philip at Claridge’s in honour of Her Majesty’s forthcoming visit to Trinidad and Tobago.
As a painter in England Boscoe Holder has exhibited at the Trafford Gallery, the Redfern Gallery, and the Commonwealth Institute in London, and at the Castle Museum, Nottingham. Two of his paintings were bought by the Leicester Galleries for their permanent collection. He also exhibited at the Martell Exhibition of Paintings, Drawings and Sculpture, held at the Royal Water Colour Society Galleries. In 1981 Sir Ellis Clarke, former President of the Republic of Trinidad and Tobago presented Prince Charles and Lady Diana with a Holder painting as a wedding gift from the Republic. Returning to Trinidad in 1970 Boscoe Holder concentrated mainly on his paintings"
As well as dancing, during these years Holder continued to paint and his work was exhibited at various UK galleries including the Trafford Gallery, the Redfern Gallery, the Commonwealth Institute, the Castle Museum Nottingham, the Martell exhibition of Paintings, Drawings and Sculpture at the Royal Watercolour Society Galleries, and the Leicester Galleries.
After being based in London for 20 years, in 1970 Holder returned to Trinidad and quickly re-established himself as a painter, "with an unbroken record of annual shows from 1979 onwards, sometimes two, three or four in a year". His work has been exhibited all over the Caribbean and elsewhere internationally. His paintings can be seen in collections throughout the world, preserving the West Indian culture. In 1981, a Holder painting was presented by the then President of the Republic of Trinidad and Tobago, Sir Ellis Clarke, as a wedding gift from the nation to Prince Charles and Lady Diana.
Boscoe is known for his keen eye for human beauty and transforming it onto the canvas. Several of his subjects fondly recall him approaching them sometimes out of the cold and offering to paint their portrait.
In 1973, in recognition of Boscoe Holder's contribution to the Arts, the government of Trinidad and Tobago awarded him the Hummingbird Medal (gold) and named a street after him.
Then-Mayor of Washington DC declared 22 May 1983 as Boscoe Holder and Geoffrey Holder Day, in recognition of the brothers' contribution to the arts.
On 31 October 2003, Boscoe Holder was awarded an Honorary Degree of Doctor of Letters (DLitt) by the University of the West Indies.