Born in Kingston, Osmond Watson was a graduate of one of the first teaching programmes created by Edna Manley at the Jamaica School of Art and Crafts. In 1961, disappointed at the failure of plans for a West Indian Federation, he decided to travel to England with the intention of furthering his studies. He registered at St Martina's School of Art, London, but spent much of his time teaching himself through visits to view the African masks at the British Museum and works of the modern masters at the Tate. After a brief stint in Paris he returned to London and remained there until 1965. Back in Jamaica, he began teaching at the Jamaica School of Art where his students included Kofi Kayiga. He also began exhibiting regularly in single person and group exhibitions including the Sao Paulo Biennial in 1971, Ten Jamaican Sculptors, Commonwealth Institute, London 1975 and the SITES: Jamaican Art 1922-1982 exhibition in Washingston USA.