Portrait of a Man is the conventional title of several male portraits finished by the Italian Renaissance artist Antonello da Messina in the course of his career. These include the famous portrait usually known as The condottiero, now in the Louvre of Paris.

Antonello da Messina, Portrait of a Man, 1460s, tempera of wood, 27 cm × 20 cm (11 in × 7.9 in), Museo Civico Malaspina, Pavia

This early portrait is one of Antonello s best-  known works. Traditionally, it is believed to have  come from the island of Lipari, where it appears to  have been used as the door of a pharmacy cupboard.  Baron Enrico Pirajno di Mandralisca acquired the por-  trait from there, sometime in the nineteenth century,  and, with the rest of his collection, it was later donated  to the city of Cefalu. A caption in an early-twentieth-  century catalogue of photographs identified the work  as a portrait of ''an unknown sailor," and it retained  that evocative title until Roberto Longhi noted (1953).  perspicaciously, that ''Antonello did not paint por-  traits of fishermen but of barons (^'baruni'y even if he  also made use of common Sicilian facial features in his  religious works/'   Scholars have unanimously accepted the attribution  of this panel to Antonello, since Di Marzo first pro-  posed it in 1899. The portrait has been plausibly dated  to the late 1460s, or perhaps between 1470 and 1472.[1]

Antonello da Messina (1430–1479), Portrait of an unknown man (late 1460's), oil on panel, Museo Mandralisca, Cefalu

This haunting portrait was painted in Sicily about 1470–72. Trained in Naples in the Netherlandish technique of oil painting, Antonello set the standard for portraiture when he came to Venice in 1475. Long before Leonardo da’ Vinci, he introduced the incipient smile as an indication of the inner life of the sitter, enveloping his features in a soft light and engaging the viewer with his direct gaze. In these ways, the picture responds to the often voiced view that painting was a mere depiction of the outward appearance of a person.[2]
From about 1470 until his death in 1479, Antonello  painted one of the most remarkable series of male portraits of the Quattrocento. Deviating from the strict profile poses generally favored by Italian painters and inspired, instead, by Netherlandish [Flemish] portraits, these bust-length images present their sitters in  three-quarter view, and almost always against a dark neutral background. This example is among the earliest, painted probably not long after the Portrait of a Man in Cefalu. The young man is simply dressed, his dark clothing and long cap setting off the thin white band of his collar and his fine, light, wavy hair (its silhouette against the outline of his face at the left is one of the most virtuosic elements of the painting). His face is animated by the movement of his pale gray eyes, the slight twist of his head, and above all by the hint of a smile — a smile that has been likened to that of a Greek kouros. While Antonello's somewhat later portraits are more monumental and have an even stronger psychological presence, the early ones are rarely surpassed for the charm and vitality of their sitters, or for the sense that they transmit the ''motions  of the mind," in Leonardo da Vinci's words. Antonello's portraits made a strong impact in Venice, where they may have influenced Giovanni Bellini in the mid- 1470s and established the basis for the portraits by Jacometto Veneziano. Although the surface has been somewhat abraded,  especially in the shadows of the flesh tones and in the  hair at the right, the panel is generally legible, and the  better part of the fine detail and modeling is intact. [0] 

This Portrait of a Man is currently housed in the National Gallery of London, United Kingdom. It was printed on the Italian 5,000 lire note issued from 1979 to 1983.
The work portrays an unknown man, whose garments belonged to the middle-upper class of the time. He wears a leather blouse, under which a white shirt is visible, and a red cloth beret.

He is depicted from three-quarters, differently from the tradition of the time. The dark background and the essential composition derived from Flemish painting school, including Petrus Christus, whom Antonello knew personally in Italy.

X-ray analysis proved that originally the eyes looked in a different direction. Perhaps there was a parapet with the signature, which was cut off later.[2] It has been suggested that this late work could be a self-portrait.[3]

Antonello da Messina, Portrait of a Man, 1475–76, panel, 25.5 cm × 35.5 cm (10.0 in × 14.0 in), National Gallery, London

This portrait, finished c. 1475, is housed in the Museo Thyssen-Bornemisza, in Madrid, Spain.
Among Antonello's portraits, it is among the most expressively animated ones. The subject, a young man, is drawn from a quite near point of view, with the usual skill in details rendering.
The picture has been approximately dated to the early 1470s, basing on the typical "zuccotto" headgear, a fashion more characteristic of 1460s Italy.

Antonello da Messina, Portrait of a Man, 1476, panel, 37.4 cm × 29.5 cm (14.7 in × 11.6 in), Turin City Museum of Ancient Art

This Portrait of a Man was signed by Antonello, and has been considered his very last work if the date on it is interpreted as 1478. It is therefore his last male portrait, and it housed in the Staatliche Museen (Gemäldegalerie) of Berlin, Germany.

Relevant is the insertion by Antonello of a landscape in the background, as other artists (including Giovanni Bellini) used this innovative feature only starting from the 1490s. The picture shows influences from the late Flemish paintings, as can be seen from the rendering of the dress, similar to a Van Eyck portrait now at Sibiu.

1. Antonello da Messina: Sicily's Renaissance Master [Gioacchino Barbera, Keith Christiansen, Andrea Bayer], The Metropolitan Museum of Art / Yale University, (2005) ISBN 10: 1588391779 ISBN 13: 9781588391773
2. Portrait of a Young Man | The Metropolitan Museum of Art | http://www.metmuseum.org/collection/the-collection-online/search/435581
3.  Page at museum's official website
4.  De Vecchi, Pierluigi; Elda Cerchiari (1999). I tempi dell'arte. Milan: Bompiani. ISBN 88-451-7212-0.

Bibliography

De Vecchi, Pierluigi; Elda Cerchiari (1999). I tempi dell'arte. Milan: Bompiani. ISBN 88-451-7212-0.

Barbera, K, ed. (2005). Antonello da Messina: Sicily's Renaissance Master. New York: The Metropolitan Museum of Art.

[1] This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Male portraits by Antonello da Messina".