doleful

From Middle English doleful, doolful, deolful, equivalent to dole +‎ -ful.

• IPA^(key): /ˈdoʊlfəl/

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• Rhymes: (General American) -oʊlfəl

doleful (comparative more doleful or dolefuller or dolefuler, superlative most doleful or dolefullest or dolefulest)

1. Filled with grief, mournful, bringing feelings of sadness.

   The doleful peal of the bell indicated another funeral was being held.

   • 1667, John Milton, “Book I”, in Paradise Lost. […], London: […] [Samuel Simmons], […], →OCLC; republished as Paradise Lost in Ten Books: […], London: Basil Montagu Pickering […], 1873, →OCLC, lines 61–69:

     A dungeon horrible, on all sides round, / As one great furnace flamed; yet from those flames / No light; but rather darkness visible / Served only to discover sights of woe, / Regions of sorrow, doleful shades, where peace / And rest can never dwell, hope never comes / That comes to all, but torture without end / Still urges, and a fiery deluge, fed / With ever-burning sulphur unconsumed.

   • 1906, Lord Dunsany [i.e., Edward Plunkett, 18th Baron of Dunsany], Time and the Gods‎, London: William Heineman, →OCLC, page 55:

     O King this is very doleful. It is told that that traveller came at last to the utter End and there was a mighty gulf, and in the darkness at the bottom of the gulf one small god crept, no bigger than a hare, whose voice came crying in the cold: “I know not.” And beyond the gulf was nought, only the small god crying.

   • 2020 April 18, Donald G. McNeil Jr., “The Coronavirus in America: The Year Ahead”, in New York Times‎:

     “We face a doleful future,” said Dr. Harvey V. Fineberg, a former president of the National Academy of Medicine.

The comparative/superlative pair "more doleful / most doleful" is significantly more common than "dolefuller / dolefullest", which is further more common than "dolefuler / dolefulest".[1][2]

• dolefully
• dolefulness