Darryl Pinckney in The NY Review of Books:
The black individual passing for white in nineteenth- and twentieth-century American fiction by white writers is usually a woman, and usually when the truth emerges, the purity of the white race is saved. However, in An Imperative Duty (1891) by William Dean Howells, a Boston girl is ashamed to find out that legally she is colored, but her white suitor marries her anyway and takes her off to a life in Italy. In the beginning of Charles Chesnutt’s The House Behind the Cedars (1900), a “high-bred” black man in North Carolina returns to his hometown to ask his sister to take his dead white wife’s place and bring up his son. A young aristocrat she meets in her new white life proposes marriage, but soon learns the truth of her origins. Literary convention, in the form of a fever, kills her. The white suitor realizes too late that love conquers all. He promises to keep the brother’s secret.
The secret was as radical as Chesnutt could get. From a North Carolina family of “free issue” blacks—meaning emancipated since colonial times—Chesnutt had blond hair and blue eyes. He wouldn’t pass for white, because if he became famous then he chanced someone appearing from his past. He preferred to pursue reputation as a black man. Chesnutt had cousins who crossed the color line and he never told on them, viewing passing as an act of “self-preservation,” a private solution to the race problem. The big escape from being black was an American tradition. Three of Sally Hemings’s six children ended up living as white people.
More here.