Synonyms of doleful

1 Syllable
sad, down
2 Syllables
joyless, mopey, grieving, mournful, saddest, painful, forlorn, rueful, mirthless, beefing, sadder, piteous, moody, moodier, wretched, woeful, drearier, dolent, tragic, somber, dreary, cheerless, dismal, gloomy, downcast
3 Syllables
crestfallen, despondent, pitiful, anguished, heartbroken, plaintive, threnodial, lugubrious, dirgeful, distressing, sorrowful, heartrending, heartsore, godawful, chapfallen, funereal, dejected, elegiac, afflicted, downhearted, splenetic, dolorous, depressed
4 Syllables
down-in-the-mouth, woebegone, heavyhearted, dirgelike, lamentable, dolesome, dolorific, melancholy, dispirited, miserable
5 Syllables
disconsolate