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.

Antonello is one of the most fascinating geniuses of Italian painting. His career remains poorly documented, and the means by which he became adept at the Netherlandish technique remain somewhat conjectural. He was born in Messina but as a young man worked in Naples with Colantonio, and there can be little doubt that it was there that he was able to study the work of Jan van Eyck and Rogier van der Weyden, for King Alfonso of Aragon owned works by both artists. Colantonio was himself adept at oil painting, which he may have learned firsthand from Franco-Netherlandish painters in the entourage of René of Anjou, who ruled the city from 1438 to 1442. By 1457 Antonello was back in Messina, though for how long is uncertain. His earliest securely dated works are all from 1473: a double-tiered polyptych, with the figures shown against a gold background, for the monastery of San Gregorio, Messina (now in the Museo Nazionale, Messina); an Annunciation, with a perspectival interior setting and a landscape viewed through windows (Museo Nazionale, Syracuse); and an Ecce Homo (Collegio Alberoni, Piacenza). The style of these differs considerably and the establishment of a precise chronology for Antonello’s paintings prior to his documented presence in Venice in 1475 remains controversial. The two paintings by Antonello in the Metropolitan—an Ecce Homo (32.100.82) and the Portrait of a Man—are universally placed in Antonello’s early activity, prior to his documented stay in Venice (whether he made more than one trip to Venice is unknown). The broad forms and generalized physiognomy of the portrait relate to the Annunciation—as does the incipient smile that enlivens the face. While the picture is frequently dated ca. 1470, about all that can be said for certain is that it is unlikely to have been painted later than 1473: both the portrait of a man in the Gemäldegalerie, Berlin, which is dated 1474, and the portrait of a condottiere in the Louvre, Paris, dated 1475, show a movement away from the generalized forms of the Metropolitan portrait. The two portraits that are usually considered earlier in date are in the Philadelphia Museum of Art and the Museo della Fondazione Culturale Mandralisca, Cefalù. As in the MMA portrait, in each of these the sitter is shown bust-length against a dark background, in three-quarter view, his gaze directed at the viewer—a convention clearly dependent on the example of Netherlandish practice, and specifically on portraits by Jan van Eyck. However, in each case Antonello introduces an expressive quality that marks a fundamental innovation, paralleled in Florence a few years later by Leonardo da Vinci. The smile of the MMA portrait—compared by Sricchia Santoro (1986) to that of a Greek kouros—is thus an early manifestation of Antonello’s interest in investing his sitters with a life-like quality. A topos of humanist literary criticism was that painters could reproduce the external likeness of a sitter, but not the inner self or character: that painted portraits lacked a voice. The impetus behind Antonello’s innovation would thus seem to be his contact with main currents of humanist thought, which he most likely encountered in Alfonso of Aragon’s court, where a literary academy was founded in 1447 (one of the members of the academy, Bartolomeo Fazio, wrote the earliest biographies of Jan van Eyck and Rogier van der Weyden as well as of Gentile da Fabriano and Pisanello, and he admired specifically the expressive character of their work; his book, the De viris illustribus, dates from 1456).

The sitter in the MMA portrait wears a hat, or capuzzo, the trailing tail of which falls over his right shoulder. His high-collared garment is worn over a white shirt (Bayer 2011). Whether his dress identifies him as a Venetian merchant living in Sicily cannot be said (Lucco 2006).

The MMA portrait is abraded and has been cut down on all four sides and it cannot be ruled out that originally the sitter was shown behind a parapet, as in the artist’s later portraits.

[2012]

Henry Willett, Arnold House, Brighton (by 1879); [Sedelmeyer, Paris, in 1896; cat., 1896, no. 64, as "Portrait of the Artist"]; [C. Hoogendijk, The Hague, by 1907–12; sale, Frederick Muller's, Amsterdam, May 14, 1912, no. 61, as attributed to Antonello da Messina, to Kleinberger]; [Kleinberger, New York, 1912; sold to Altman]; Benjamin Altman, New York (1912–d. 1913)

London. Royal Academy of Arts. "Winter Exhibition," January 6–March 15, 1879, no. 196 (as "Portrait of the Painter," by Antonello da Messina, lent by Henry Willett).

London. New Gallery. "Exhibition of Early Italian Art from 1300 to 1550," 1893–94, no. 132 (as "Portrait of Antonello da Messina," by himself, lent by Henry Willett).

Amsterdam. Rijksmuseum. "Catalogue des tableaux. . . du musée de l'état à Amsterdam," 1911, no. 367 a (as "Portrait of a Young Man," by Antonello, lent by Mr. C. Hoogendijk).

New York. The Metropolitan Museum of Art. "Art Treasures of the Metropolitan," November 7, 1952–September 7, 1953, no. 84.

New York. The Metropolitan Museum of Art. "Venetian Paintings in the Metropolitan Museum," May 1–September 2, 1974, no catalogue.

New York. The Metropolitan Museum of Art. "From Van Eyck to Bruegel: Early Netherlandish Painting in The Metropolitan Museum of Art," September 22, 1998–February 21, 1999, not in catalogue.

New York. The Metropolitan Museum of Art. "Antonello da Messina: Sicily's Renaissance Master," December 13, 2005–March 5, 2006, no. 5 (as "Portrait of a Man").

New York. The Metropolitan Museum of Art. "The Renaissance Portrait from Donatello to Bellini," December 21, 2011–March 18, 2012, no. 147.

Illustrated Catalogue of the Third Series of 100 Paintings by Old Masters . . . Paris, 1896, p. 112, no. 64, ill.

Bernard Berenson. Letter. November 7, 1912, attributes this picture to Antonello da Messina.

Max J. Friedländer. Letter to Mr. Kleinberger. November 26, 1912, considers it a "beautiful original" by Antonello da Messina.

Catalogue des tableaux anciens dépendant des collections formées par M.-C. Hoogendijk de La Haye. Frederik Müller, Amsterdam. May 14, 1912, p. 22, no. 61.

"The Benjamin Altman Bequest." Metropolitan Museum of Art Bulletin 8 (November 1913), p. 233.

Handbook of the Benjamin Altman Collection. New York, 1914, pp. 60–61, refutes the idea that it is a self-portrait and dates it well after 1465.

Adolfo Venturi. "La pittura del Quattrocento." Storia dell'arte italiana. 7, part 4, Milan, 1915, p. 28, fig. 13.

Bernard Berenson. Venetian Painting in America: The Fifteenth Century. New York, 1916, pp. 30–31, fig. 16, suggests that it was painted in Milan in 1476 and comments on the "curious Luinesque aspect of the sitter".

François Monod. "La galerie Altman au Metropolitan Museum de New-York (1er article)." Gazette des beaux-arts, 5th ser., 8 (September–October 1923), pp. 179, 188–90, ill.

Bernard Berenson. "Una santa di Antonello da Messina e la pala di San Cassiano." Dedalo 6 (1925–26), pp. 638, 645, ill.

Bryson Burroughs. The Metropolitan Museum of Art: Catalogue of Paintings. 9th ed. New York, 1931, p. 7, believes the sitter to be "about seventeen".

Lionello Venturi. Pitture italiane in America. Milan, 1931, unpaginated, pl. 284.

Bernhard Berenson. Italian Pictures of the Renaissance. Oxford, 1932, p. 25.

Johann Lauts. "Antonello da Messina." Jahrbuch der kunsthistorischen Sammlungen in Wien, n.s., 7 (1933), p. 56, fig. 54, dates it to the first half of the 1470s.

Lionello Venturi. "Fifteenth Century Renaissance." Italian Paintings in America. 2, New York, 1933, unpaginated, pl. 379, dates it after the portrait by Antonello in the Johnson collection in Philadelphia.

Helen Comstock. "The Connoisseur in America: Van Marle's Attributions to Antonello da Messina." The Connoisseur 94 (December 1934), p. 394.

Raimond van Marle. "The Renaissance Painters of Central and Southern Italy." The Development of the Italian Schools of Painting. 15, The Hague, 1934, pp. 494–96, fig. 298, dates it before 1470.

Hans Tietze. Meisterwerke europäischer Malerei in Amerika. Vienna, 1935, p. 328, pl. 66 [English ed., "Masterpieces of European Painting in America," New York, 1939, p. 312, pl. 66].

W. R. Valentiner. "Christ at the Column by Antonello da Messina." Bulletin of the Detroit Institute of Arts 14 (January 1935), p. 44.

Bernhard Berenson. Pitture italiane del rinascimento. Milan, 1936, p. 21.

Stefano Bottari. Antonello da Messina. Milan, [1939], pp. 75–76, 82, 137, 145, pl. 41 [see Ref. Zeri and Gardner 1973], dates it 1472 or 1473.

Jan Lauts. Antonello da Messina. Vienna, 1940, pp. 21, 38, pl. 33, mentions it among Antonello's late portraits, including those of young men in the Johnson Collection, Philadelphia Museum of Art, and in the Kaiser-Friedrich-Museum, Berlin [now Gemäldegalerie], noting that the latter is dated 1474.

Harry B. Wehle. The Metropolitan Museum of Art: A Catalogue of Italian, Spanish, and Byzantine Paintings. New York, 1940, pp. 174–75, ill., notes that it has been seriously damaged by overcleaning, although the most important parts are intact.

Margaret Breuning. "Metropolitan Re-Installs Its Treasures in Attractive Settings." Art Digest 18 (June 1, 1944), p. 6.

Art Treasures of the Metropolitan: A Selection from the European and Asiatic Collections of The Metropolitan Museum of Art. Exh. cat., The Metropolitan Museum of Art. New York, 1952, p. 225, no. 84, colorpl. 84.

Giorgio Vigni. Tutta la pittura di Antonello da Messina. Milan, 1952, p. 22, pl. 17, dates it about 1470; comments on its ruined state, noting that at this point it tells us little about Antonello.

Stefano Bottari. Antonello. Milan, 1953, pp. 23, 97, pl. 74 [see Ref. Zeri and Gardner 1973].

Luigi Coletti. Pittura veneta del Quattrocento. Novara, 1953, p. 65, dates it to the artist's Venetian period, after 1475.

Stefano Bottari. Antonello da Messina. Greenwich, Conn., 1955, p. 16, pl. 4.

Bernard Berenson. Italian Pictures of the Renaissance: Venetian School. London, 1957, vol. 1, p. 6.

Giorgio Vigni. All the Paintings of Antonello da Messina. New York, 1963, pp. 13, 24, pl. 13.

Raffaello Causa. Antonello da Messina. Milan, 1964, unpaginated.

Gabriele Mandel. L'opera completa di Antonello da Messina. Milan, 1967, p. 91, no. 30, colorpl. 11, dates it 1470 and comments on the compromised state of the picture.

Francis Haskell. "The Benjamin Altman Bequest." Metropolitan Museum Journal 3 (1970), p. 275.

Burton B. Fredericksen and Federico Zeri. Census of Pre-Nineteenth-Century Italian Paintings in North American Public Collections. Cambridge, Mass., 1972, pp. 10, 523, 606.

Federico Zeri with the assistance of Elizabeth E. Gardner. Italian Paintings: A Catalogue of the Collection of The Metropolitan Museum of Art, Venetian School. New York, 1973, p. 1, pl. 1, observe that this picture was long known as a self-portrait, but that Antonello had not yet achieved such an accomplished style when he was as young as this sitter appears to be; date it about 1470.

Bernard Berenson. Looking at Pictures with Bernard Berenson. New York, 1974, pp. 252–53, ill. (color).

Maria Grazia Paolini. "Antonello e la sua scuola." Storia della Sicilia. 5, Naples, 1979, p. 32.

Gioacchino Barbera in Antonello da Messina. Exh. cat., Museo Regionale, Messina. Rome, 1981, pp. 109–10, no. 12, ill., discusses the dating.

Jessica Rutherford. "Henry Willett as a Collector." Apollo 115 (March 1982), pp. 178–79, ill.

Fiorella Sricchia Santoro. Antonello e l'Europa. Milan, 1986, pp. 102, 159–60, no. 19, places it in the early 1470s, when Antonello "resolutely took on the problem of Italian formal synthesis".

Joanne Wright in "Antonello the Portraitist." Antonello da Messina. Messina, 1987, pp. 187, 189, fig. 9, calls our picture the "high point of the first phase of Antonello's portraiture" and dates it about 1473.

Ellen Markgraf Bochum University. Antonello da Messina und die Niederlande. Frankfurt am Main, 1990, pp. 112, 118, fig. 29, dates it about 1470, comparing it with Antonello's other early portraits of this date in the Museo della Fondazione Mandralisca, Céfalu, the Museo Civico Malaspina, Pavia, and the Philadelphia Museum of Art.

Luciana Arbace. Antonello da Messina: catalogo completo dei dipinti. Florence, 1993, pp. 46–47, no. 15, ill. (color), dates it to the beginning of the 1470s.

Dominique Thiébaut. Le Christ à la colonne d'Antonello de Messine. Exh. cat., Musée du Louvre. Paris, 1993, pp. 103–4, ill.

Maryan W. Ainsworth. Petrus Christus: Renaissance Master of Bruges. Exh. cat., The Metropolitan Museum of Art. New York, 1994, p. 65 n. 79.

Joanne Wright in The Dictionary of Art. 2, New York, 1996, p. 180.

Gioacchino Barbera. Antonello da Messina. Milan, 1998, p. 50, ill. (color).

Chiara Savettieri. Antonello da Messina. Palermo, 1998, pp. 15, 122, no. 3, ill., dates it to the beginning of the 1470s.

Giuseppe Consoli Guardo. Antonello fuori dai luoghi comuni. Milan, 2001, pp. 105, 108, considers it a portrait of Giovanni Bellini, but offers no explanation for this identification.

Andrea Bayer in Antonello da Messina: Sicily's Renaissance Master. Exh. cat., The Metropolitan Museum of Art. New York, 2005, p. 44, no. 5, ill. p. 45 and frontispiece (color), states that Antonello's early portraits, like this one, "are rarely surpassed for the charm and vitality of their sitters"; mentions the impact of Antonello's portraits on Venetian art, and their possible influence on Giovanni Bellini and Jacometto.

Mauro Lucco in Antonello da Messina: l'opera completa. Exh. cat., Scuderie del Quirinale, Rome. Cinisello Balsamo (Milan), 2006, pp. 164–65, 174, 196, no. 15, ill. (color).

Karen Wilkin. "Antonello da Messina at the Met." New Criterion 24 (February 2006), p. 48.

Maria Clelia Galassi. "Aspects of Antonello da Messina's Technique and Working Method in the 1470s: Between Italian and Flemish Tradition." Cultural Exchange Between the Low Countries and Italy (1400–1600). Turnhout, Belgium, 2007, p. 69, based on an email from Dorothy Mahon of June 19, 2002, states that examination of the painting with infrared digital photography has revealed a very faint underdrawing, adding that this indicates that assumptions about the lack of underdrawing on Antonello's panels may sometimes be untrue.

Andrea Bayer in The Renaissance Portrait from Donatello to Bellini. Exh. cat., Bode-Museum, Berlin. New York, 2011, pp. 335–37, no. 147, ill. (color) [German ed., "Gesichter der Renaissance: Meisterwerke italienischer Portrait-Kunst," Berlin, 2011].

Sabine Hoffmann in The Renaissance Portrait from Donatello to Bellini. Exh. cat., Bode-Museum, Berlin. New York, 2011, pp. 282, 340 [German ed., "Gesichter der Renaissance: Meisterwerke italienischer Portrait-Kunst," Berlin, 2011, p. 340].

Patricia Rubin in The Renaissance Portrait from Donatello to Bellini. Exh. cat., Bode-Museum, Berlin. New York, 2011, p. 6.

Andrew Butterfield. "They Clamor for Our Attention." New York Review of Books 59 (March 8, 2012), p. 12, ill. on cover (color).