Orlando Greenwood was born in Nelson, Lancashire. He studied at Goldsmith's College, London before signing up with the Royal Engineers at the outbreak of the First World War. After the war he began exhibiting in London and achieved considerable success. An account of this period is summed up in the catalogue for the artist's studio sale,

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"At this time he was hailed by some critics as ‘undeniably brilliant’ (The Sunday Times), while the Daily Mirror saw the success of his 1925 exhibition at Spinks in London as a ‘triumph’ and ‘…a direct challenge to the ultra-modernists, since Mr Greenwood is in the best tradition of painting’. At this exhibition, Greenwood sold twenty-eight out of thirty works on view, for the then considerable sum of £2,500 – half of them selling within the first half-hour of the show opening. "

Christies, Paintings, Watercolours, Drawings and Artist’s Materials from the Studio of Orlando Greenwood (11 October 1990)

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Greenwood exhibited throughout his life at the Royal Academy, Royal Society of British Artists, the Royal Society of Portrait Painters as well as many commercial galleries including the Goupil and Colnaghi. His work can be found in the Manchester City Art Gallery, the Towneley Hall Gallery and the Grundy Art Gallery (examples can be seen here).