While living in Cleveland, he began publishing stories, which appeared in various magazines, including Atlantic Monthly. His first book, The Conjure Woman, appeared in 1899. In its style, setting in the pre-war plantations of the South, and its use of dialect, the book is reminiscent of the works of Joel Chandler Harris, but Chesnutt differs from Harris in his scathing attacks on the institution of slavery. He continued writing short stories (The Wife of His Youth and Other Stories of the Color Line; 1899, and a biography of Frederick Douglass. He also wrote three full-length novels, but these were not as successful as his short stories.
It was only toward the end of his life that Chesnutt won real recognition as a prominent African American author. Throughout most of his career he was forced to rely on his law practice to support himself. He died in 1932.