The word “doleful” is often employed to evoke a mood of deep melancholy or sorrow, enriching the emotional landscape of a work. It can modify voices to convey lamentation or regret, as when a character’s expression is described as dour and mournful [1, 2, 3]. Poets and prose writers alike use the term to paint vivid pictures of gloomy settings or heavy-hearted farewells—from the somber toll of bells in verse [4, 5] to the lingering, pained cry of a spirit burdened by misfortune [6, 7]. In its varied usage, “doleful” not only describes sound and expression but also stands as a metaphor for the pervasive atmosphere of despair that marks the human condition, as seen in works that range from epic narratives [8] to intimate personal reflections [9].