The American novelist Sherwood Anderson rejected the emphasis on plot that was common among his precursors and promoted a new mode of writing. In seeking to express the ineffable feelings and emotional realities of humans, he created narratives to imitate the core features of a character. Published in 1919, Winesburg, Ohio (1919), a collection of short stories, expresses what lies behind surface realities, with multiple sensory images and visually arresting scenes. Intentionally highlighting the grotesque features of a character, the tales arouse a sense of eeriness in the reader’s mind but, ultimately, lead one to rethink what is beautiful and lovable. By focusing on the first Winesburg tale, “Hands,” this paper unravels the meanings that can be drawn from Anderson’s representation of the main character. Given the interesting affinities between Anderson and Vincent Van Gogh, who sought to examine the emotional realities of human beings, this paper reads “Hands” alongside The Potato Eaters by Van Gogh.