Rejecting his era's genteel hypocrisy about miscegenation and "passing," Chesnutt—as novelist, short story writer, and public intellectual—spoke out against disfranchisement, lynching, and the legal underpinnings of segregation, laying bare the deep contradictions at the heart of American attitudes toward race and history. Chesnutt's first book, The Conjure Woman (1899), is a collection of richly detailed stories set in a world of fantastic powers and occult influence, yet rooted in the realities of post-bellum North Carolina. After the success of these stories, Chesnutt went on to become one the most important African American writers of his time, even if the true measure of his achievement went unrecognized until decades after his death.

Chesnutt's novels The House Behind the Cedars (1900) and The Marrow of Tradition (1901), as well as the stories in The Wife of His Youth and Other Stories of the Color Line (1889), are penetrating explorations of a society giving way to violence and a racist status quo, and the prescient views put forth in his essays and lectures continue to yield insight into the way Americans regard themselves and each other.