Here are some synonyms for doleful:
* Sorrowful
* Mournful
* Gloomy
* Melancholy
* Depressed
* Despondent
* Wailing
* Lugubrious
Examples:
* "The doleful sound of the funeral dirge filled the air."
* "Her doleful expression betrayed the pain she was feeling."
* "The doleful news of his death spread quickly through the town."
Origin:
The word "doleful" comes from the Middle English word "dolful," which itself comes from the Old English word "dol," meaning "sad" or "stupid."