doleful

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

• IPA^(key): /ˈdoʊlfəl/

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.

   • 1674 — John Milton. Paradise Lost, Book I, 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.

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