The two–Mona Lisa theory is a longstanding theory proposed by various historians, art experts, and others that Leonardo da Vinci painted two versions of the Mona Lisa.Dianne Hales, Mona Lisa: A Life Discovered (2014), p. 251.John R. Eyre, Monograph on Leonardo da Vinci's Mona Lisa (1915).Christian Gálvez, Gioconda descodificada: Retrato de la mujer del Renacimiento (2019), p. 195, quoting Léon Roger-Milès, Leonard de Vinci et les Jocondes (1923). Several of these experts have further concluded that examination of historical documents indicates that one version was painted several years before the second.

The journalist Dianne Hales has noted that "the two–Mona Lisa theory has been around a long time", observing that the sixteenth-century painter and art theorist Gian Paolo Lomazzo identifies two versions of the painting in his 1584 Treatise on Painting. The theory itself may be impossible to definitively prove or disprove, but proponents of the theory highlight a number of pieces of documentary and physical evidence. Among these is the fact that there are several paintings of which Leonardo is known to have painted two versions, and historical accounts such as Lomazzo's writing suggesting that Leonardo similarly worked on two paintings, a Gioconda and a Mona Lisa. Furthermore, various accounts contain inconsistencies and incompatibilities with respect to the dates when Leonardo began and ended work on the painting, by whom it was commissioned, the state of completion in which it was left, and what ultimately became of it. These inconsistencies and incompatibilities are asserted to be broadly resolved with the explanation that there were two versions of the painting having different dates of initiation and states of completion, painted for different patrons, and having different profiles and fates.

Also cited as a key piece of evidence is a contemporaneous sketch of the painting by Raphael, who observed the painting while visiting Leonardo's studio. The sketch contains characteristics differing from the Mona Lisa in the Louvre, including prominent columns that were initially argued to have been trimmed from the original. However, in 1993, it was demonstrated that the painting in the Louvre had never been trimmed, bolstering claims that Raphael saw a different version of the painting. Other descriptions by eyewitnesses and others living in the period have also been read as indicating that Leonardo painted two paintings of the subject of the Mona Lisa, with several characteristics differing from the painting in the Louvre.

The author John R. Eyre made an extensive case for the theory in his 1915 Monograph on Leonardo da Vinci's Mona Lisa, and Léon Roger-Milès made a similar case in his 1923 book, Leonard de Vinci et les Jocondes. Several more recent examinations of the evidence have led other authors to similar conclusions. While it is possible that a first version was produced by Leonardo and later lost or destroyed, proponents of the theory have identified a number of existing alternative versions of the Mona Lisa as candidates for having also been painted by Leonardo. These include versions more similar to the original such as the Prado Mona Lisa, but more particularly those versions that closely resemble Raphael's sketch and other historical accounts, such as the Vernon Mona Lisa (which is no longer considered a candidate after tests showed that it was painted after Leonardo's death), and the Isleworth Mona Lisa, the latter having received the most substantial support.

Evidence cited for the theory Propensity for painting multiple versions of works A number of authors have noted that Leonardo often painted two versions of his works, and also often left works unfinished, leaving his students to complete the missing portions. For example, Frank Zöllner wrote of Leonardo's two versions of the Virgin of the Rocks,Frank Zöllner, Leonardo da Vinci, 1452–1519 (2000), p. 30. and Eyre, in his 1915 monograph, wrote that Leonardo "almost invariably commenced two versions of each of his works, which he rarely finished", citing the Virgin of the Rocks along with two versions of Saint John the Baptist and of Leda and the Swan, and two versions each of drawings of Isabella d'Este, the Adoration of the Magi, and Saint Anne.

References to multiple versions of the Mona Lisa Dianne Hales quotes the sixteenth-century painter and art theorist Gian Paolo Lomazzo as identifying two versions of the painting: "In 1584, in his Treatise on Painting, the Florentine artist and chronicler Giovanni Paolo Lomazzo, a supposed acquaintance of Leonardo's longtime secretary Melzi, wrote that 'the two most beautiful and important portraits by Leonardo are the Mona Lisa and the Gioconda'''". Another statement considered as evidence for this purpose was made by Fra Pietro da Novellara in a 1501 letter to Isabella d'Este, Marchesa of Mantua, detailing Leonardo's activities from a visit to his studio. Fra Pietro states in the letter that "[t]wo of his pupils are painting portraits, and he touches them up from time to time".Letter from Fra Pietro da Novellara to Isabella d'Este, Marchesa of Mantua (March 22, 1501), in John R. Eyre, Monograph on Leonardo da Vinci's Mona Lisa (1915), p. 16-17.E. L. Scott, "Yet Another "Mona Lisa" Adds to Mystery of Louvre Picture", Deseret News (February 14, 1914), p. 25. Eyre and Eugène Müntz both discuss Fra Pietro's letter, with Müntz deeming the subjects unknown,Eugène Müntz, Léonard da Vinci, l'artiste, le penseur, le savant, vol. 2 (1899), p. 11. and Eyre concluding that these were portraits of Lisa del Giocondo.

Raphael's sketch A number of experts have argued that Leonardo made two versions based on the differences in details in Raphael's sketch. Circa 1505, Raphael executed a pen-and-ink sketch, in which columns flanking the subject are substantially more apparent. Experts universally agree that this sketch was based on Leonardo's portrait. Other later copies of the Mona Lisa, such as those in the National Museum of Art, Architecture and Design and The Walters Art Museum, also display large flanking columns. As a result, it was thought that the Mona Lisa had been trimmed. However, by 1993, Frank Zöllner observed that the painting surface had never been trimmed; this was confirmed through a series of tests in 2004. In view of this, the art historian Vincent Delieuvin, curator of sixteenth-century Italian painting at the Louvre, states that the sketch and these other copies must have been inspired by another version, while Zöllner states that the sketch may be after another Leonardo portrait of the same subject.

Disparities in dates of production and completion Disparate dates proposed for the initiation and completion or abandonment of the Mona Lisa are claimed to indicate that there were actually two different paintings worked on at different times, with one version being begun in 1503 and left unfinished, and the Louvre Mona Lisa being begun after 1513. Specifically, it is believed by some that Leonardo da Vinci had begun working on a portrait of Lisa del Giocondo, the model of the Mona Lisa, in Florence by October 1503. Although the Louvre states that it was "doubtless painted between 1503 and 1506", Leonardo experts such as Carlo Pedretti and Alessandro Vezzosi are of the opinion that the Louvre painting is characteristic of Leonardo's style in the final years of his life, post-1513. Other academics argue that historical documentation indicates that Leonardo would have painted the work in the Louvre from 1513.

In 2005, a scholar at Heidelberg University discovered a marginal note in a 1477 printing of a volume by the ancient Roman philosopher Cicero. The note was dated October 1503, and was written by Leonardo's contemporary Agostino Vespucci. This note likens Leonardo to the renowned Greek painter Apelles, who is mentioned in the text, and states that Leonardo was at that time working on a painting of Lisa del Giocondo. In response, Delieuvin stated, "Leonardo da Vinci was painting, in 1503, the portrait of a Florentine lady by the name of Lisa del Giocondo. About this we are now certain. Unfortunately, we cannot be absolutely certain that this portrait of Lisa del Giocondo is the painting of the Louvre".

The art historian Martin Kemp, while doubting the two-painting theory, nevertheless notes difficulties in confirming the dates with certainty, and the sixteenth-century biographer Giorgio Vasari wrote of Leonardo's work on the Mona Lisa that "after he had lingered over it four years, [he] left it unfinished", though the painting in the Louvre appears to be a finished piece. Proponents of the theory explain that the hypothetical first portrait, displaying prominent columns, would have been commissioned by Giocondo circa 1503, of a younger sitter (Lisa del Giocondo being 23 years old in 1503), and left unfinished in the possession of Leonardo's pupil and assistant Salaì until Salaì's death in 1524. The second, commissioned by Giuliano de' Medici circa 1513, would have been sold by Salaì to Francis I of France in 1518 and is the one in the Louvre today. Notably, even those who believe that there was only one true Mona Lisa have been unable to agree between the two aforementioned fates, or to otherwise account for the incompatibility of the facts of record with only one painting.

Disparities over the commission Different sources provide inconsistent information about the identity of the patron for whom the Mona Lisa was painted. In his 1923 book, Leonard de Vinci et les Jocondes, Léon Roger-Milès argues that Leonardo actually painted at least two versions of the Mona Lisa, including one for Francesco del Giocondo, and another for Giuliano de' Medici. According to Vasari, the painting was created for the model's husband, Francesco del Giocondo. However, the record of an October 1517 visit by Louis d'Aragon states that the Mona Lisa was executed for the deceased Medici, Leonardo's steward at the Belvedere Palace between 1513 and 1516.—though some have suspected this to be an error, hypothesizing that this refers to yet another portrait by Leonardo "of which no record and no copies exist".

Scholars have also developed several alternative views as to the subject of the painting, with some historically having argued that Lisa del Giocondo was the subject of a different Leonardo portrait, and identifying at least four other paintings as the Mona Lisa referenced by Vasari. Several other women have been proposed as the subject of the painting in the Louvre. Isabella of Aragon, Cecilia Gallerani, Costanza d'Avalos, Duchess of Francavilla, Isabella d'Este, Pacifica Brandano or Brandino, Isabella Gualanda, Caterina Sforza, Bianca Giovanna Sforza—even feminized versions of Salaì and Leonardo himself—are all among the list of posited models portrayed in the painting. Based on this assertion, it is proposed that Leonardo painted a different painting actually depicting Lisa del Giocondo.

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