Antonello's ability to grasp the intimate essence of the person will lead Antonello da Messina to become one of the greatest portrait painters of all time. This particular skill is revealed since his first Portrait of a Man, dated approximately around 1465-68: here the portrayed, with a sudden jerk of the head and a slightly ironic expression, almost seems to spy on the observer's space. On the low parapet appears the writing, simulating an engraving, in capital letters: “ANTONELLUS MESSANEUS PINXIT”. It is the vindication of an early masterpiece. In this small walnut panel (which measures only 27 x 20 cm) we find the essential data of what the Sicilian painter will be: the presentation of the subject on a dark background half-length, cut just below the shoulder, portrait of three quarters, with thin-lipped mouths, barely puckered by a hint of a smile, and a slightly mocking look that never leaves the observer. The details of the face correspond to the physiognomic data of a character.