Sir Osbert was the author of poems, short stories, novels, and memoirs. Most of his verse is light and satiric. His works include: Triple Fugue (1924), short stories; Before the Bombardment (1926), a novel; Collected Poems and Satires (1931); Selected Poems (1943); Four Songs of the Italian Earth (1948); Collected Stories (1953); The Four Continents (1954), discursions on travel, art, and life; and Tales My Father Taught Me (1962).
His five-volume reminiscences about his family are a delightful account of British society of the Edwardian era— Left Hand, Right Hand (1944), The Scarlet Tree (1946), Great Morning (1947), Laughter in the Next Room (1948), and Noble Essences (1950). Upon his father's death in 1943, he became 5th baronet.
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