There are several drawings depicting the face, or the assumed face, of Leonardo da Vinci.
This one situated in Venice, made with red pencil on red colored paper, represents three-quarter view of an elderly man, frowning with bushy eyebrows, protruding forehead, long hair and beard and deep, intelligent eyes looking at the observer.
This version of Leonardo’s three-quarter view portrait (apart from this, the version in the Biblioteca Reale of Turin and a sculpture by Quadrelli for example) has been the most prevalent over the centuries, thanks to large number of reproductions.

Some have considered it a copy from the 16th century of the famous self-portrait of Turin (Biblioteca Reale, inv. 15571 DC) and others have suggested this is the original one and the one in Turin is the copy, but today it is quite generally accepted as a possible drawing on which Giuseppe Benaglia based his engraving for the frontispiece of the book by Bossi on Leonardo’s Last Supper (1810).
On page 263 of the aforementioned volume there’s a list of illustrations and Bossi himself mentions the sheet: “This print, by Mr. Giuseppe Benaglia, was not taken from the original drawing by Leonardo (ignoring its whereabouts) but from a copy made by Mr. Raffaello Albertolli. Albertolli was a professor of ornamental studies at the Accademia di Brera, where Bossi worked as a secretary.

This attribution, however, can be quite perplexing because the drawing has the appearance of a 16th century design. In case it was really a copy from the 19th century, the painter would have made a skilled fraudulent version from the original one: he used original tools such as red chalk instead of pastel, which was well-pointed like Leonardo and his followers’ tools, but above all he used ancient paper, which had a reddish tint. However, the style is not typical of Leonardo, who was left-handed, and for this reason the hypothesis of the purposely made forgery was rejected. Bossi himself was a skilled executor of copies of da Vinci’s drawings, but a red chalk design requires a great virtuosity and moreover, the executor made the work with free hand, in order to not to lose its naturalness and to recreate an image that had the same strength and thickness of the original one.
Following this track (see Perissa Torrini), the conclusion suggests that whoever completed this design did not intend to create a copy or a forgery, but to recreate a prestigious ancient drawing in the most faithful way.

The red chalk work was added to the collection of Gallerie dell’Accademia of Venice with Bossi’s materials in 1818.

Bibliografia essenziale:
Pedretti C., in Disegni di Leonardo da Vinci e della sua scuola alla Biblioteca Reale di Torino, a cura di C. Pedretti (catalogo di mostra Firenze 1975), pp. 4-5;
Pedretti C., in I disegni di Leonardo da Vinci e della sua cerchia nella Biblioteca Reale di Torino, ordinati e presentati di C.
Pedretti, con la riproduzione integrale dell’opera inedita Disegni d’architettura militare di Leonardo da Vinci, Firenze 1990, n.1;
Pedretti C., in L’immagine di Leoanrdo. Testimonianze figurative dal XVI al XIX secolo, a cura di R.P. Ciardi, C. SIsi (catalogo di mostra Vinci 1997), pp. 71-73, n. 1.2;
Perissa Torrini A., in I Disegni di Leonardo da Vinci e della sua cerchia nel Gabinetto dei Disegni e delle Stampe delle Gallerie dell’Accademia di Venezia, a cura di Pedretti, Nepi Scirè, Perissa Torrini, Firenze 2003, pp. 167-168, n. 72 (con bibliografia precedente);

Leonardo was born in Anchiano in 1452. He was an illegitimate son of notary Ser Piero di Vinci who brought him to Florence in 1469 to give him artistic education.

In 1472 he enrolled to the Compagnia dei Pittori and attended Andrea del Verrocchio’s workshop, participating also in the anatomical research with Antonio and Piero Pollaiolo.

In 1482 Leonardo moved to Milan to serve Ludovico il Moro. He introduced himself as a musician, painter, sculptor, engineer and architect. He painted several works in the court of Moro, among them the Lady with an Ermine and worked on the equestrian monument for Francesco Sforza.

He was a set designer for various court celebrations and studied hydraulic and military engineering. He also devoted himself to physical and natural sciences, as shown in many of his drawings. His most famous work of this period was the Last Supper in Santa Maria delle Grazie (1495 – 1498) where he experimented with tempera on plaster technique instead of the traditional fresco. This resulted in poor state of conservation, which Vasari already mentions in the mid-16^th century.

Ludovico il Moro was defeated by the French in 1500 and Leonardo set off to Venice with his friend, mathematician Luca Pacioli and his student Salai. Then he went to Mantua as a guest of Isabella d’Este and painted her portrait. In the same year he returned to Florence, where he painted Madonna and Child with St. Anne (Louvre, cartoon at the National Gallery of London) and the cartoon for the Battle of Anghiari (1504-1505) for the Salone dei Cinquecento in Palazzo Vecchio.

He was commissioned by the Gonfaloniere of the Florentine Republic, Pier Soderini, who had also commissioned Michelangelo, who was working with the Battle of Cascina. Leonardo experimented with ancient encaustic technique, which turned out to be unsuccessful. Therefore, the project was not completed and today only some drawings have remained of the lost cartoon, such as the Tavola Doria.

Leonardo traveled to Urbino, Pesaro, Rimini and Cesenatico where he continued to study hydraulics, cartography and fortifications, but in 1505 he returned to Milan. He made several trips between Lombardy, Florence and Rome and continued his science research, but he was never commissioned by the Vatican, which favored the works of Raphael and Michelangelo.

Disappointed Leonardo left Italy in 1517 to take refuge in the castle of Cloux, near Ambroise in France, under the protection of Francis I, who gave him an annual pension. He brought numerous paintings with him, like Mona Lisa, which he painted in Florence in 1503. In France he continued his anatomical and scientific studies of which he left many drawings.

Leonardo died in 1519.

The Accademia of Venice was founded in 1750 and the opening of the Gallerie dell’Accademia was linked to it with primarily educational purpose: in 1803 a decree established the need to adjoin a gallery next to the school that was used by the students who studied painting and sculpting.

In 1817 the gallery was opened also to the public. The gallery is located in the area of Dorsoduro, down by the Accademia bridge, in a complex including the church of Santa Maria della Carità, the Canonici Lateranensi convent and the Scuola Grande of Santa Maria della Carità, all situated in a single floor, divided into twenty-fours and covering 5537 square meters.

The first section of the collection includes the Presentation of the Virgin at the Temple and the Pietà by Titian (1538) and the Triptych of the Madonna della Carità by Antonio Vivarini and Giovanni d’Alemagna (1480). The collection also includes essays by the students of the academy and a collection of plaster casts (hence the plural name, gallerie) which were put on display in the exhibition with success in 1817.

The collection was enriched with the paintings brought from defeated France and with the masterpieces that were left to the museum by great collectors. However, the paintings were always linked to the Venetian culture and this feature was tried to overcome for the whole 20th century. Among these works was the legacy of Felicita Reiner (in 1833, but only formalized in 1850), which included masterpieces such as Piero della Francesca’s St. Jerome, Giovanni Bellini’s Madonna and Child and Saints Catherine and Mary Magdalene. The legacy of Girolamo Contarini (1838) included 180 works, among them Madonna of the Small Trees and the Four Allegories by Bellini, and six paintings by Pietro Longhi.

The emperor Franz Joseph grew the collection with Nicolò di Pietro’s Madonna and Mantegna’s St. George, Memling’s Portrait of a Young Man and Giorgione’s Old Woman. The gallery was radically reorganized in 1895 by the director Giulio Cantalamessa. He excluded all the 19th century artists and for the first time the exhibition was organized chronologically. He coordinated the cycles of the School of St. Ursula by Vittore Carpaccio and the School of St. John the Evangelist by Cima da Conegliano, previously divided in various locations. Under the direction of Gino Fogolari (1905) the museum acquired other fundamental masterpieces, such as the Tempest by Giorgione and the Crucifixion by Luca Giordano and the Feast at the House of Simon by Bernardo Strozzi.

In the post-war period the museum performed various changes, for example Titian’s Assumption of the Virgin, which was supposed to be placed in a specially designed room, was returned to the Frari church in Venice instead. The 19th century works that were already excluded from the exhibition were sent to the deposit at the museum of Modern Art in Ca’ Pesaro and the foreign art in the Galleria Giorgio Franchetti in Ca’ d’Oro. In the 1940s’ Vittorio Moschini and Carlo Scarpa wanted to perform a modern reorganization of the museum, including the 19th century salons, but which resulted quite impractical in the end. In these years Francesco Guardi’s Fire in the Oil Depot of San Marcuola and Montagna’s St. Peter and Donor became part of the collection.

In 1987 director Sciré decided to increase the exhibition space opening the gallery on the fourth floor with the graphic collection and a new deposit was opened on the top floor of the Palladio building. In the same year the collection was enriched with two cherubs and two allegorical figures representing Justice and Patience, taken from Giorgio Vasari’s ceiling in a room of Palazzo Corner on the Grand Canal. Between 2001-2003 the gallery was renovated expanding the exhibition areas and adding modern lightning in the rooms.