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Biblical Symbolism in Leonardo da Vinci’s Mona Lisa*


By Mikhail Epstein


The Montréal Review, July 2022


Leonardo’s Mona Lisa, or La Gioconda, remains the most enigmatic painting in the history of art. I’ll venture to share a hunch I had when I stood for a long time in front of this painting in the Louvre. Before us is the subtlest variation of a biblical subject: the image of Eve seduced by the serpent, as if she had absorbed his outlines into herself, into the curves of her cloak, of her eyes and lips. The genius of Leonardo is that the serpent is presented not only as a separate figure along with Eve, but also permeates her body and clothing, coiling and twisting her from within as it passes through her.

Compare figures 1 and 2. It is difficult not to discern the reptile lurking behind the Mona Lisa.

Fig. 1. Mona Lisa, or La Gioconda (1503–1506).

Fig. 2. The Mona Lisa with the outline of the serpent.


When one perceives Gioconda and the landscape around her as a whole, one cannot help being struck by the outline of a serpent looming behind her. The enormous reptile lies just beyond the balustrade of the balcony where Gioconda sits. Behind her left shoulder, the monster’s head can be seen jutting into the right frame of the painting; its tail continues in the form of a road winding behind and above her right shoulder. The head is given in profile, so that one eye is clearly visible, just above the mantle thrown over Gioconda’s left shoulder, and we see most of the serpent’s closed mouth (some is cut off by the right frame). Applicable to this giant monster protruding from the landscape, and at the same time forming its foreground, are the verses from Genesis: “And the LORD God said unto the serpent, Because thou hast done this, thou art cursed above all cattle, and above every beast of the field; upon thy belly shalt thou go, and dust shalt thou eat all the days of thy life” (3: 14–15). This strange silhouette behind the back of Gioconda-Eve has no clearer visualization than a reptile.

Fig. 3. This is roughly the appearance of the reptile whose head peeks out from behind Gioconda’s left shoulder, and whose tail wriggles in the form of a road behind her right shoulder. (Author’s photo.)

There is also something vaguely serpentine about Gioconda’s face, above all in her lips, which curve into a subtle sneer. The shadows from the corners of her lips reinforce this impression. But even more striking than the “snakiness” of Gioconda’s famous smile are her elongated eyes, and their lack of eyelashes. This anomaly can be explained if we compare it to the physiognomic peculiarity of snakes: their eyes are not protected, though they are always open, even when they sleep. No wonder Satan took the form of a serpent: the unblinking, ever-open eye stands as an expression of impertinence, as if defying the light created by God on the first day of creation, and therefore God himself. In the human face, by contrast, the presence of eyebrows and eyelashes, fringing the eyes and protecting them from the bright light, is a sign of humility.

The combination of the images of a woman and serpent, of course, brings to mind the biblical episode of the Fall. It is known that Leonardo was deeply interested in this subject and dedicated to it his first painting, Adam and Eve, which has not survived. According to Giorgio Vasari, Leonardo was commissioned to produce this work after painting the angel in the Baptism; it constituted “a cartoon for a tapestry to be woven of gold and silk in Flanders and sent to the King of Portugal, showing Adam and Eve when they sinned in the earthly paradise.”1 In his historical novel Resurrected Gods. Leonardo da Vinci (1900), recognized as one of the deepest insights into Leonardo’s life and creation, Dmitrii Merezhkovsky establishes a direct link between Gioconda and the Eve of da Vinci’s initial canvas. In the Mona Lisa, Leonardo’s pupil Giovanni “saw the same smile ... as on the foremother Eve before the Tree of Knowledge in his teacher’s first painting.”2

Of course, the Mona Lisa features no traditional scene of temptation, no Satan appearing before Eve in the guise of a serpent to offer her the forbidden fruit. Here the temptation has already taken place, and we see Gioconda-Eve now marked with the serpent’s seal, having absorbed the features of the tempter. There is no tragedy, no horror, no dramatic intrigue here, but neither is there a serene scene of paradise. We see the world immediately after the Fall, where Eve and the serpent have become almost one, and the outlines of the serpent move smoothly from the landscape to the lines of her lips and eyes, to the mantle on her shoulder, the curves of her hair and the folds of her clothes. Gioconda is the serpent in the form of a woman, and a woman who has become the serpent.

This whole impression of the painting was expressed in a phrase—a vivid verbal brushstroke—by the notable art historian Abram Efros, who wrote in the mid-1930s: “This is not the portrait of Francesco del Giocondo’s wife, but the image of some half-human, half-snake creature, either smiling or frowning, dominating the chilled, barren, craggy space that stretches out behind her.”3

Efros conveys his impression quite accurately, but leaves it undeciphered. What is this strange, dual, “chimerical” creature in the painting? Eve and Satan are not mentioned, although it is obvious that the painting cannot but correlate with the biblical source that links a woman and a serpent. The surroundings are also expressively described: “a chilled, barren, craggy space.” Obviously, this landscape must also correlate with Eden, where an encounter between a woman and a serpent determined the fate of humanity. It is this desolate Eden that we contemplate in Leonardo’s painting, where only the trail of the serpent, drawn into a majestic but mournful terrain, reveals the cause of Eden’s transformation into something like a barren moonscape.

The slightly twisted mantle thrown over Gioconda’s shoulder also produces a snake-like curve, which continues with the dark, curly hair framing her face and falling over her shoulders. Serpentine, too, are the ringlets curling in gold threading along the neckline of the dress. On the sleeves are wavy folds that, in their curvature and “frothiness,” contrast with the quiet position of the hands. The same sly curve lies snakily on Gioconda’s mouth, deepening the shadows that fall on the whole lower half of her face, condensing over her upper lip and under the lower one, and giving them the appearance of a forked sting.

Notable is the dark circle right at the serpent’s jaw (in the lower right corner of the painting). More precisely, the half-circle, as it is cut off by the frame. It looks like half of the fruit that Eve-Gioconda took a bite of—or did she split it with the serpent? In some paintings, like that of Albrecht Dürer, the serpent himself brings the fruit in his mouth to Eve.

Fig. 4. Albrecht Dürer, Adam and Eve (1507).

This Dürer painting, we might recall, was created at the same time as Leonardo’s La Gioconda (1503–1506). But the contrast between Leonardo’s Eve and that of other artists, including Dürer, Cranach the Elder, and Titian, is glaring. The Eves of the latter remain full-bodied, ruddy. They are tempted by the serpent, but nothing has changed in their appearance. With Leonardo, the serpentine enters into Eve’s very being, from her intertwined hair under a serpentine veil, to the serpentine ornamentation of her dress and the serpentine folds on its sleeves. This is an amazing example of fractal art, where similar patterns recur at progressively smaller scales, and however much you divide the whole into parts, each remains a semblance of the whole. Eve- Gioconda is all made up of snakes, slithering from her hair, eyes, eyebrows, and lips into the patterns and folds of her clothing. In biblical scenes of the Fall, even those executed by the greatest artists, Eve and the serpent invariably come into contact only externally, through the forbidden fruit. Only in Leonardo does the serpent possess Eve from within. Next to such an Eve, no Adam nor Tree of Knowledge—the usual attributes of such biblical scenes—are needed; the Fall permeates Eve-Gioconda’s being, the flesh and fabric of her sly and cunning existence. Other artists seem too literary next to Leonardo, who turned the subject into a manner of painting, displaying the serpentine nature of the brush itself.


In England, La Gioconda became famous in 1869 thanks to the essayist and art historian Walter Pater, who wrote: “She is older than the rocks among which she sits; like the vampire, she has been dead many times, and learned the secrets of the grave; and has been a diver in deep seas, and keeps their fallen day about her; and trafficked for strange webs with Eastern merchants; and, as Leda, was the mother of Helen of Troy, and, as Saint Anne, the mother of Mary; and all this has been to her but as the sound of lyres and flutes, and lives only in the delicacy with which it has moulded the changing lineaments, and tinged the eyelids and the hands.”4

For my part, I tend to think this woman is even older than Leda or St. Anne. She is the first of women—the first of all people—to taste the fruit of the Tree of Knowledge of good and evil. In her person, the whole human race, tempted by the serpent, gains self-knowledge. “So God created man in his own image, in the image of God created he him; male and female created he them” (Genesis 1: 27). There is not much specifically female in Gioconda’s face, which could also belong to a man. Not without a reason, some researchers believe that the model for La Gioconda was the author himself, that is, the painting constitutes a self-portrait in women’s clothing. In Leonardo’s Hidden Face, the American scholar David Schwartz states that computer studies of Leonardo’s self-portrait “superimpose perfectly” with that of the Mona Lisa.5  

Fig. 5.  Mona Lisa and Leonardo

According to Merezhkovsky, this “phantom-like creature—summoned by the will of the teacher—[is] a shapeshifter, a female double of Leonardo himself…. Leonardo and the Mona Lisa are like two mirrors, which, reflecting one in the other, deepen to infinity.”6 This may serve as evidence of the unified, “androgyne” nature of Gioconda as both male and female, both Adam and Eve in the mystery of their “panhuman” fall.

Gioconda’s smile has elicited many interpretations—some quite bizarre.7 Does the smile have what could be called psycho-theological significance? Obviously it is not a luminous expression of joy or amiability; it is a smile of involuntary submission to sin, and at the same time a consciousness of one’s free will, which stubbornly asserts the right to sin. At the risk of being carried away by overly free associations, I would suggest that a similar smile plays on the lips of the heroine of Lars von Trier’s Nymphomaniac, named Joe (could this be a reference to Gioconda?), as she is ready to indulge in rampant fornication. She smiles again and again before committing yet another abuse of herself and trampling on the nature of love. That smile says, “That’s what I am! And so are we all! We know we do wrong. But we can’t change it.” It is at once guileful and innocent—the smile of a being who can understand sin in herself, but not overcome it. Such a being lives in quasi-freedom: she has the freedom of consciousness, but no freedom of will and action. This discrepancy is what the smile expresses. Gioconda’s smile is part defiant, part apologetic: “Having already succumbed to temptation, I can’t help myself.”

Also involved in Gioconda’s smile are her eyes, elongated by shadows, and echoing the outline of her lips. Their expression is not so definite; one cannot say that the eyes are smiling. But they do know what her lips are smiling at, and they share this knowledge with us. They look calm and contemplative, but there is a half-question, half-recognition in them: “I can imagine what you know. Can’t you imagine what I know?” Hence the mixture of shyness and slight mockery in that look: the understanding that such knowledge should be hidden—and that it is impossible to hide. There is no surprise or fear in this gaze, but a quiet acceptance of the inevitable.

Humans are capable of self-consciousness, but not of self-control at the deepest levels of their being. Whether it is genes, or chemistry and hormones, or instincts or archetypes, the Socratic “know thyself” does not translate into Seneca’s “rule thyself.” This helpless awareness is expressed in a smile, at once sly and defenseless. There is an acceptance of one’s guilt and weakness and, at the same time, a kind of narcissism, a volitional affirmation of one’s servitude.


That the figure of the serpent should go unnoticed for centuries in the world’s most famous painting is surprising. There is a recently discovered curious precedent of hidden snake imagery in Leonardo’s previous work. Using the program Paint X, Grigol Keshelava has detected the figure of a snake in Lady with an Ermine (1490). "The ermine holds the cobra’s head and small front of his body with his right paw. One gets the impression that this is the end of the battle between ermine and snake...  We think that the ermine, who looks like a mongoose in dimensions, is associated with Ludovico Sforza. In the crossed serpent, Leonardo implies any danger from which Ludovico protects Cecilia." This observation points to Leonardo’s idiosyncratic predilection for imаges of veiled snakes in his female portrait paintings. 

A similarly unexpected discovery was made by the New York-based designer Ron Piccirillo as he viewed the Mona Lisa from a forty-five-degree angle. From this standpoint, he found a great number of hidden figures in the outline of the rocks: a lion, a monkey, a buffalo, a crocodile—a whole zoo!8 Piccirillo offers no definitive explanation for his find. But if we agree that the painting depicts a postlapsarian Eden, then the images of the animals are understandable, and so is the reason for their remaining hidden, barely delineated. The primordial paradise had teemed with animals; they are present even in scenes of the Fall, as in Lucas Cranach the Elder’s Adam and Eve (1526).

Fig. 6. Lucas Cranach the Elder, Adam and Eve (1526).

The serpent, wrapped around the Tree of Knowledge, watches as Eve hands over the fruit to Adam, surrounded by a menagerie of lion, rhinoceros, deer, horse, doe, sheep, stork... But in Leonardo’s painting, if we believe Piccirillo’s conjectures, these animals are hidden, as if gone into the rocks, petrified in them, because Eden itself is now off-limits to people. Of all animals, only the triumphant serpent remains visible and, as we have shown, its contour runs through the entire picture, uniting portrait and landscape.

Dmitrii Merezhkovsky was among the first to realize this amazing resonance between portrait and landscape. “The streams curled between the rocks just as her lips curl in a perpetual smile. And the waves of her hair fell from beneath a transparent-dark haze according to the same laws of divine mechanics as do waves of water.”9 But the question is: is this really the working of divine mechanics?

Suddenly we realize that the space behind Gioconda represents an uncultivated, desolate land—a postlapsarian land: there is not a single tree, not a single fruit, none of the plants and animals that were created at the beginning of Genesis and that filled Eden. It is a stony soil that, from now on, man is condemned to cultivate in the sweat of his brow. It is a land of yearning and toil—harsh, hard, dreary. Eve-Gioconda, with an all-knowing smile on her lips, appears as its progenitor, who opened these winding paths to a fallen world.

People and serpents, and people as serpents—this is an ancient and archetypal motif in art. In the famous sculptural group Laocoön and His Sons (200 BC), the plastic male bodies are shaped by their deadly struggle with snakes. In the image of Gioconda, it is the other way around: the snake smoothly enfolds a female body submissive to it, all the way up to a sly grin on gentle lips. In one of Leonardo’s prose passages, he mentions the allegorical figure of Envy, represented as a woman with “a heart gnawed by a swelling serpent.”10 No other signs of envy are revealed by the image of Gioconda, but it is significant that Leonardo conceives of an image of a woman as united with an image of a snake gnawing at her heart.

Incidentally, the name Gioconda itself may have not only biographical but also linguistic overtones. The painting is thought to be a portrait of Lisa Gerardini, wife of the Florence silk merchant Francesco del Giocondo, thus La Gioconda. Consonance here conjures the name of the largest snake, the anaconda, a word that most likely comes from the Latin anacandaia. This resonance between “Gioconda” and “anaconda” may have served as an additional motivation for the introduction of serpent shapes in the image of Gioconda and her surroundings.

The demonic overtones of this image have been pointed out by many scholars, but in the style of free association, without linking it to the pictorial leitmotif of the painting—the figure of the serpent. Richard Muther states in his History of Painting (1912): “What fascinates the spectator is the demoniacal charm of this smile. Hundreds of poets and writers have written about this woman, who now seems to smile upon us seductively and now to stare coldly and lifelessly into space, but nobody has solved the riddle of her smile, nobody has interpreted her thoughts. Everything, even the scenery is mysterious and dream-like, trembling as if in the sultriness of sensuality.”11

The prominent Russian philosopher Aleksei Losev (1893–1988) sounds a sharper, even denunciatory note about Leonardo’s “demonicity,” noting the heroine’s “devilish smile”: “After all, one only has to look into the eyes of Gioconda, and one can easily see that she is, in fact, not smiling at all. It is not a smile, but a predatory face with cold eyes and a distinct knowledge of the helplessness of the victim whom Gioconda wants to possess.”12

Let us return to the beginning, to the first impression: a majestic woman, a charming smile; around her, peaceful nature... If the Fall had been presented as a dramatic scene, full of movement, passion, desperation, and shock, the picture would have achieved an entirely different effect, closer to Raphael’s The Fall of Man or a corresponding scene in Michelangelo’s Sistine Chapel fresco. Leonardo, however, does not address the biblical scene directly, but rather conveys the quiet, gradual ingrowth of original sin into the ordinariness of human existence. The serpentine has entered the soul and flesh of this woman in a quite worldly, graceful way. The mystery of the Fall blends into a secular subject, a portrait of a Florentine woman.

Friedrich Schiller interpreted the nature of the aesthetic effect thus: “[T]he true search of the master consists in destroying matter by the form; and the triumph of art is great in proportion as it overcomes matter and maintains its sway over those who enjoy its work. It is great particularly in destroying matter when most imposing, ambitious, and attractive, when therefore matter has most power to produce the effect proper to it.”13 In Leonardo’s painting, the matter, the thematic content as represented by the young woman, is “most imposing, ambitious, and attractive” indeed; while the form, which revives the biblical archetype of original sin, is deeply tragic and distressing. The immense aesthetic impact of the painting can be explained precisely by the fact that its external plot—a charming, ornate, smiling woman against a decorative sublime  landscape—comes into conflict with its internal plot of irresistible seduction and fall.


Mikhail N. Epstein is a Russian–American cultural and literary scholar. He is Samuel Candler Dobbs Professor of Cultural Theory and Russian Literature at Emory University (USA). From 2012 to 2015, he served as Professor and Founding Director of the Centre for Humanities Innovation at Durham University (UK). Epstein has authored 39 books and more than 800 articles and essays. His work has been translated into 24 languages. His latest books include: The Transformative Humanities: A Manifesto (Bloomsbury Academic, 2012); The Irony of the Ideal: Paradoxes of Russian Literature (Boston: Academic Studies Press, 2017); Russian Postmodernism: New Perspectives on Post-Soviet Culture (with A. Genis and S. Vladiv-Glover; Berghahn Books, 2016). A Philosophy of the Possible: Modalities in Thought and Culture (Brill, 2019); The Phoenix of Philosophy: Russian Thought of the Late Soviet Period (1953-1991) (Bloomsbury Academic, 2019); Ideas Against Ideocracy: Non-Marxist Thought of the Late Soviet Period (1953–1991) (Bloomsbury Academic, 2022).


* A version of this article first appeared in Russian: Mikhail Epshtein, “Bogoslovie v kraskakh. Ot grekhopadeniia do voznesenia i ot Leonardo do Salvadora Dali” (“Theology in Colors: From the Fall to Ascension and from Leonardo da Vinci to Salvador Dali”), Zvezda (St. Petersburg), no. 3 (2015): 221–231. I am grateful to the Boston-based artist Alexandra Rozenman for her technical assistance in drawing the contour of the serpent in fig. 2.

1 https://erenow.net/biographies/leonardo-da-vinci-the-flights-of-the-mind/17.php

2 D. Merezhkovskii, Voskresshie bogi, book 14 (“Mona Lisa”), http://az.lib.ru/m/merezhkowskij_d_s/text_0060.shtml.

3 Abram Efros, “Leonardo – khudozhnik” (“Leonardo the Artist”), http://vinci.ru/ef_03.html.

4 Walter Pater, The Renaissance: Studies in Art and Poetry (1893), https://www.gutenberg.org/files/2398/2398-h/2398-h.htm.

5 Renzo Manetti, David Schwartz, and Alessandro Vezzosi, Mona Lisa: Il volto nascosto di Leonardo / Leonardo’s Hidden Face (bilingual edition) (Florence: Edizioni Polistampa, 2007).

6 Merezhkovskii, Voskresshie bogi (Resurrected Gods).

7 For example, some dentists explain Mona Lisa’s mysterious smile as an attempt to conceal her missing front teeth. One group of researchers has maintained that the sitter’s mouth is so firmly shut because she was undergoing mercury treatment for syphilis, which turned her teeth black. Medical practitioners diagnose a lipoma and facial nerve palsy; a Danish doctor attributes Gioconda’s large hands to a congenital palsy affecting the left side of her face. Experts at the University of Amsterdam have even undertaken to break down the complex range of feelings expressed by Mona Lisa’s smile: 83% joy, 9% disgust, 6% fear, and 2% anger. Alice Shirrell Kaswell, “Mona Lisa: All Things to Some Researchers,” http://www.neatorama.com/2010/12/28/mona-lisa-all-things-to-some-researchers.

8 Christina Ng, “Mona Lisa’s Secret: Hidden Animals?,” https://abcnews.go.com/blogs/headlines/2011/12/mona-lisas-secret-hidden-animals.

9 Merezhkovskii, Voskresshie bogi.

10 https://www.fromoldbooks.org/Richter-NotebooksOfLeonardo/section-10/item-677.html.

11 Cited from S. Freud, Leonardo da Vinci. A Psychosexual Study of an Infantile Reminiscence, trans. A. A. Brill (1916), https://www.gutenberg.org/files/34300/34300-h/34300-h.htm.

12 A. F. Losev, Estetika vozrozhdeniia (The Aesthetics of the Renaissance) (1978), https://thelib.ru/books/losev_aleksey/estetika_vozrozhdeniya-read-37.html.

13 J. C. Friedrich von Schiller, “Letters upon the Aesthetic Education of Man” (1794), letter 22,  https://sourcebooks.fordham.edu/mod/schiller-education.asp.


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