- 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.