Orlando Greenwood was born at Nelson and worked at his uncle's mill from the age of thirteen. He studied at Nelson Technical School before studying art at Goldsmith's College, London, in 1913. He never exhibited any of his work at Towneley. At the start of the war, he enlisted and became a draughtsman in the Royal Engineers Regiment.
After the war, he continued to live in London. He was elected an Associate Member of the Royal Society of British Artists in 1920 and a Full Member in 1922. By 1922 he was establishing a national reputation as a painter. He became famous for his oil paintings of still lifes of porcelain figures arranged in classically inspired tableaux. At his first one-man show in 1925, Greenwood sold twenty-eight out of thirty works on view, for the then considerable sum of £2,500. At this time he also received commissions for portraits of the aristocracy. (Burnley Express December 9th 1925, page 8 col.3 Nelson Weaver-Artist now a famous painter )
His celebrity status did not last long but he continued to paint a variety of still-lifes, landscapes and architectural studies until his retirement from painting in 1967. There are works by him in four other galleries in the UK.
Orland Greenwood is represented in the collections by six oil paintings, three watercolours and two etchings. The first painting was purchased in 1945 and the first gift to Towneley from a local collector of his work arrived in 1974. The other works were mostly purchased after his death, mainly from his studio sale in 1990, at which time a palette and four paintbrushes were purchased. This palette is not the large one that was often seen in photographs of him in the 1920s.