Doleful

doleful
    adj 1: filled with or evoking sadness; "the child's doleful
           expression"; "stared with mournful eyes"; "mournful news"
           [syn: {doleful}, {mournful}]
    

Doleful \Dole"ful\, a.
   Full of dole or grief; expressing or exciting sorrow;
   sorrowful; sad; dismal.
   [1913 Webster]

         With screwed face and doleful whine.     --South.
   [1913 Webster]

         Regions of sorrow, doleful shades.       --Milton.

   Syn: Piteous; rueful; sorrowful; woeful; melancholy; sad
        gloomy; dismal; dolorous; woe-begone. -- {Dole"ful*ly},
        adv. -- {Dole"ful*ness}, n.
        [1913 Webster]
    

60 Moby Thesaurus words for "doleful":
      affecting, afflicted, aggrieved, anguished, blue, careworn,
      cast down, cheerless, crestfallen, dejected, depressed, depressing,
      disconsolate, dispirited, distressed, distressing, dolorous, down,
      down-in-the-mouth, downhearted, dreary, dumb with grief, forlorn,
      funereal, gloomy, grief-stricken, griefful, grieved, grieving,
      grievous, harrowing, heartrending, in grief, joyless, lamentable,
      lugubrious, melancholy, miserable, mournful, mourning, moving,
      pathetic, piteous, pitiable, pitiful, plaintive, plangent,
      plunged in grief, rueful, ruthful, sad, sorrowed, sorrowful,
      sorrowing, tearful, touching, unhappy, woebegone, woeful,
      wretched