Antonello da Messina transformed the Renaissance portrait in paintings like this one, in which the face emerges from the dark background and the sitter’s steady gaze confronts the viewer. Messina was one of the first Italian artists to adopt the Netherlandish use of oil, which gave his paint surfaces a luminosity that egg tempera, then the primary painting medium in Italy, could not achieve. This method served him particularly well in his portraits, which were considered the greatest in fifteenth-century Italy.

Portrait of a Young Gentleman,” 1474, by Antonello da Messina