Colescott was an influential American painter and draftsman who gained renown for works in which he inserted Black figures into canonical Western paintings. Taking the most famous portrait in the world as its point of departure, that enigmatic smile replaces the woman of the Mona Lisa with a grinning "mammy" figure, resembling the racist caricature known as Aunt Jemima. Despite its humor, this work is a somber meditation on privilege and representation. The jovial subject is not permitted to have an enigmatic smile, and an image of Aunt Jemima is not a portrait at all. Colescott once said, "If you decide to laugh, don't forget the humor is the bait, and once you've bitten, you may have to do some serious chewing. The tears may come later. "
Inscriptions and markings: On drawing in graphite, between two ruled lines: "that enigmatic smile;" Signed and dated recto, lower right: "R. Colescott 79".