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1866, John Keegan Casey, “Maire My Girl”, in A Wreath of Shamrocks, Dublin: Robert S. McGee, page 20:
On the brown harvest tree Droops the red cherry.
1949 January and February, F. G. Roe, “I Saw Three Englands–1”, in Railway Magazine, page 12:
Long before Shap platform showed up around a corner and the two arms on the gradient post drooped in both directions at once, Duchess of Buccleuch's amiable throbbing purr at the stack [funnel, chimney] had become a fierce freight-engine bark, as she resolutely dragged at her enormous load.
I'm not handsome in the classical sense. The eyes droop, the mouth is crooked, the teeth aren't straight, the voice sounds like a Mafioso pallbearer, but somehow it all works.
Long after his cigar burnt bitter, he sat with eyes fixed on the blaze. When the flames at last began to flicker and subside, his lids fluttered, then drooped; but he had lost all reckoning of time when he opened them again to find Miss Erroll in furs and ball-gown kneeling on the hearth[…].
1944 September and October, A Former Pupil, “Some Memories of Crewe Works—I”, in Railway Magazine, page 285:
Others who conscientiously attended the Technical College at night often drooped over their desks in a doze, and one does not wonder at it.
2010, john g rees, Halocline:
His head had drooped with his hair across his face.
2012, Howie Carr, Hard Knocks:
She was trying to hang in, but her chin was drooping onto her chest.
1667, John Milton, “Book XI”, in Paradise Lost., London: [Samuel Simmons], and are to be sold by Peter Parker; nd by Robert Boulter; nd Matthias Walker,, →OCLC; republished as Paradise Lost in Ten Books:, London: Basil Montagu Pickering, 1873, →OCLC, lines 175-178:
[…] let us forth, I never from thy side henceforth to stray, Wherere our days work lies, though now enjoind Laborious, till day droop[…]
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But when the melancholy fit shall fall Sudden from heaven like a weeping cloud, That fosters the droop-headed flowers all. And hides the green hill in an April shroud :