Picasso and Stein: A Study

Benjamin Botkin
12 min readJan 9, 2023

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The first time I saw Pablo Picasso’s Portrait of Gertrude Stein (1906), I felt a need to engage with it. The painting is practically begging to be engaged with. Stein leans forward, as if she is listening intently to whoever she is sitting across from. And yet, her face is stern, frozen, emotionless. The feeling I felt looking upon Stein was akin to the feeling of sharing a poem with a parent as a teenager: the desperate need to inspire an emotional reaction, combined with the inability to do so. I have never been so frustrated by a painting’s inability to stare back at me. Pablo Picasso felt just as frustrated making the piece as I felt viewing it. Picasso’s style was described by Stein herself to be predicated upon what is seen, not on what is remembered. As Stein herself explained, “when [Picasso] saw an eye, the other one did not exist for him and only the one he saw did exist for him… he was right, one sees what one sees, the rest is a reconstruction from memory… [painters have] nothing to do with memory… only with visible things.” If this is accepted as a true description of Picasso’s style, this makes Picasso’s portrait of Stein curious. Lucy Belloli notes that in August of 1906, after painting Stein over the course of “80 or more separate sittings… [Picasso] completed the painting in the absence of his model,” by memory. It was something in the face of Gertrude Stein that confounded Picasso so. X-ray studies of the portrait have found that the majority of “The alterations we see in the portrait of Gertrude Stein are concentrated in the area of the head.” Whatever it was that Picasso saw in Stein’s face frustrated his artistic principles, and this frustration is felt by the viewer when the portrait is gazed upon. What was it about Stein that frustrated Picasso to such a degree?

Gertrude Stein was an American writer and an art collector, born of a wealthy family in Philadelphia. Stein had not had “an early or independent history in art or art history,” and was introduced to the art world by her brother, Leo Stein, who “began as the mentor with the more discerning eye.” The Steins discovered Picasso in 1905, and although “it is Leo, not Gertrude, who discovers the youthful Picasso,” it is the relationship and patronage of Gertrude Stein which proves the most fruitful. Victor Giroud notes that “Leo came to disapprove of Picasso’s artistic evolution whereas Gertrude remained a friend and ally to the end,” as she herself became a collector of greater prominence and importance of her brother. Even from the early years, Gertrude was seen “at once as ‘the great man of the family… her calm certitude impressed me more than Leo’s trenchant affirmations, for the latter often changed, bearing witness to a basic instability.” The description of Stein as the “Man” of the family is an important piece of her mystique and identity. At the time Gertrude Stein met Picasso for the first time, she was writing “Melanctha,” a “reworking of Q.E.D. (quod erat demonstrandum), Stein’s first autobiographical novel… the story of Stein’s early moral crisis over romantic friendship and sexual intimacy between women.” Picasso had painted lesbians before, but Stein was different. Picasso had previously painted lesbians as “either vampiric ladies of the night- lustful, bloodless, even spectral creatures- or they are represented as purely sexual bodies, nonsubjects trapped in a narcissistic relation of proximity.” Stein behaved in a manner that was not stereotypically feminine. Chris Coffman notes that “Stein once wrote of Pablo Picasso, Henri Matisse and herself that the two men have ‘a maleness that belongs to genius. Moi aussi, perhaps.’ Stein’s early association of her ‘genius’ with ‘maleness’ points to… a form of transmasculinity inscribed through homosociality with other ‘geniuses’.” Gertrude Stein was a woman who demanded that she be treated and seen as a man would, and maybe it was this maculine persona which defined the “calm certitude” which set her apart from her brother, making her the “great man of the family.” Gertrude Stein was not a lesbian that Pablo Picasso could sexualize and objectify as he had done in the past.

Picasso became acquainted with the Steins after Leo Stein purchased his painting, Young Girl with a Flower Basket, a painting which Picasso composed during a fruitful trip to Holland, during which the young artist painted women, fascinated with their eroticism and sensuality. Picasso’s Holland paintings seem to some critics to be a moment when the artist “no longer [tried] to compose works of meaning, of symbolism or of mystery,” more interested in the physiques of his models than in any meaning which those physiques may hold. In short, Picasso objectified his models as sensual objects of desire.

Young Girl with a Flower Basket is no different, depicting “a single nude figure, a young girl just at the end of adolescence… face… no longer that of a child, with a large painted mouth and a heavy glance, lacking in innocence.” While the piece was strong enough to encourage Leo to purchase, Gertrude had a very negative reaction to it, finding herself “repelled by the ugly legs, the overlarge feet.” The physique is odd, but the restraint of the piece in it’s sensuality is most telling. The subject in flower basket has her eyes turned to the viewer, but her lower body turned away, hiding the source of her femininity, her sensuality. This, along with her adolescent body, which has not fully developed, and lacks many of the characteristics commonly associated with “womanhood,” gives the piece an androgyny. This androgyny is then juxtaposed with sensuality of the woman’s face, giving the portrait tension. This tension would be explored at great length in Picasso’s works to come.

The details surrounding Picasso’s decision to paint Stein’s portrait are lost to history. Reports are conflicting. Gertrude Stein claimed that neither her or Picasso could remember exactly, how the decision was reached, but Robert Lubar claims that there is sufficient evidence to suggest that the portrait was undertaken by Picasso as a means of developing a closer relationship to Leo Stein. This is possible. However, Picasso’s model and Lover, Fernande Olivier, who was present when Picasso first met Gertrude, suggested in 1906 that Picasso was simply, “so attracted by Mile. Stein’s physical presence that he suggested he should paint her portrait, without even waiting to get to know her better.” This may have had to do with how untraditional Stein was physically, as a model. Olivier described Stein as “fat, short, and massive… a beautiful strong head with fine, pronounced, regular features, and intelligent eyes… her voice, indeed her whole appearance is masculine.” But what differentiated Stein, in the eyes of Olivier and maybe in the eyes of Picasso himself, was the confidence with which the Steins held themselves, being “rich and intelligent enough not to worry about looking ridiculous and are so self-assured they wouldn’t care what other people think anyway.” This confidence bled into the way Picasso and Stein related with one another upon one of their first meetings over dinner, when Picasso “snatched a piece of bread from her and claimed it as his,” and Gertrude laughed at him, embarrassing Picasso. In this instance, Picasso tried to assert dominance over a woman, and was humiliated for it, collapsing the hierarchy of gender which Picasso understood. Picasso, who was already concerned with the shaky footing upon which sexual identity stood, may have been fascinated with this, leading to his decision to paint Stein.

The Portrait of Gertrude Stein is often compared and contrasted with the portraits which inspired it, portraits which the Steins had acquired and which Picasso’s portrait would be displayed with. These portraits, Picasso surely would have felt the need to compete with, but to minimize the influence these portraits had upon Picasso’s portrait to a matter of mere “one-upmanship” is intellectually lazy. However, some elements of the portrait are direct responses, and in some sense rejections, of the works of others.

Most notably, Picasso restricts his color palette to dark brownish-reds in order to separate himself from Woman with a Hat by Henri Matisse, a brightly colored sporadic piece which the Steins acquired in 1905, which Leo Stein himself described as “the nastiest smear of paint I had ever seen.” However, that smear of paint quickly made a splash in the art world, and Picasso became “‘Sullen and inhibited’ when… [the painting] took the floor at the Steins’ apartment and ‘shone and impressed people.’” By making his panting as dark in color and limited in palette as it is (browns, reds, and little else), Picasso intentionally paralleled himself to Matisse making himself an antithesis to Picasso, marking the beginning of a great rivalry.

Picasso may have also been influenced by Matisse’s use of props in Lady with a Hat. Matisse portrays his subject with a fan, symbolizing her femininity. Matisse’s portrait was not the only piece recently acquired by the Steins to use that exact symbol.

Paul Cezanne’s 1878 portrait of Madame Cezanne with a Fan, acquired by the Steins in 1905, uses the same symbol of a fan to represent femininity. A comparison between this piece and Picasso’s portrait is especially fruitful. Firstly, the color palettes are quite similar (dark browns and reds and greys). Secondly, the subjects are quite similar. Cezanne’s portrait depicts a woman, seated, her androgenous body reclined in her chair, her face mask-like and masculine. Picasso was famous for his use of mask-like imagery, and this portrait was one of the first uses of this technique. Although “The general consensus has been that the incised and irregular features of Gertrude’s mask like face derive from fifth-sixth-century Iberian stone carvings… examples of which were on view in the Louvre in the spring of 1906,” the influence of Cezanne on this piece in particular. However, the way in which the sitter is positioned alters the meaning of these masks in meaningful ways. Cezanne’s sitter is reserved. She is somewhat reclined into her chair. Her arm goes across her chest, closing herself off. Her legs are crossed, closing her off from the audience even more. She holds the fan, the symbol of her femininity, in an upright position, like a blade. For this reason, her mask-like visage relates to how the sitter has hidden herself from the artist and the viewer, hiding behind a mask in the same way in which she hides behind the rest of her body. Picasso’s mask, on the other hand, has more to do with himself than with the sitter. Stein does not look straight ahead, like Cezanne’s sitter had done. She looks to the side, away from the viewer’s natural vantage point. She does not recline. She leans forward, engaged with something besides the viewer. It is worth noting that those in attendance for the sessions in which Stein sat for her portrait was herself, Picasso, “and Fernande, the latter of whom reads aloud La Fontaine’s fables to amuse the sitter.” Picasso painted a lesbian woman as preoccupied with something other than him in an environment where the only thing which could have distracted that woman was another woman. This could be indicative of the feelings of sexual inadequacy and masculine insecurity which a woman like Gertrude Stein made him feel. This is also indicated by the lack of an aforementioned prop, the lack of a fan or of any traditional indication of femininity. Picasso insteads presents his model with her left hand firmly plated on her knee, while her left hand “hangs limply between her massive thighs, whereas Bertin’s hand is firmly planted on his knee… which suggests a certain ex- cess, a prosthetic phallus of sorts.” Stein is masculinised, and when one considers that the hand which hangs like a phallus, her right hand, is the hand that the aspiring author wrote with, one could say that Stein is masculinized by her intellect.

Stein is masculinized in one other fashion. Picasso’s portrait bears resemblance to another portrait that the Steins had recently acquired, an 1832 portrait of Louis François Bertin by Jean Auguste Dominique Ingres.

This portrait is of a man, but Picasso has imposed many of those man’s qualities upon Stein. Chris Coffman notes that Stein’s “ruffled shirt… was typically feminine clothing at the time, but also resembles the white shirt and collar Bertin wears in Ingres’s painting.” This reflection of Ingres’ portrait is also seen in the way Stein is seated, which Coffman identifies as the “‘reverse’ position of the ‘authoritative’ stance taken by LouisFrançois Bertin… The ‘corpulence’ and ‘dominance of pictorial space’ shown in [the Ingres portrait being] nineteenth-century signifiers of men’s success.” Picasso has imposed signifiers of male dominance upon a woman, suggesting the way in which Stein has crossed the gender boundaries which Picasso had known and understood. Picasso hints at the way in which the boundaries have been crossed in the way in which Stein’s body is framed. different. While Ingres’s sitter “strikes a posture of monumental composure; with its abstract golden background… Gertrude appears to exceed the spatial boundaries of the picture… positioned between the planes of two walls that press in upon her ample body.” Picasso is suggesting that Stein does not fit into the barriers which he has created for her, both literally and metaphorically.

And yet, something about Stein remains hidden away behind that mask. As previously stated, Cezanne utilizes a mask to show how his model hid herself away from the audience. But Stein is not hiding from anyone. She is not threatened by the artist. She doesn’t seem to be threatened by anyone. This makes her mask seem contradictory. One can’t imagine why a woman of her force would require one. However, this supposed contradiction presupposes one great misunderstanding; this contradiction presupposes that Stein has put the mask she wears on herself. Vincent Giroud observes that “Picasso gave Gertrude, in short, a Spanish face. It has much in common with his celebrated Self-Portrait with a Palette.” Gertrude Stein has had the face of Pablo Picasso imposed upon her. Picasso could allow himself to paint object as they were, to paint women with “no longer… meaning… symbolism or… mystery,”because he understood what they were. They fit into his understanding of what a woman was. Stein did not fit into this definition. If Picasso could not “see [Stein] any longer when [he looked],” as Stein claims that she had told him, then that was because Pablo refused to see Stein, hence why he imposes his own face upon her. He cannot see past himself.

The Stein portrait is often seen as a precursor to Picasso’s most famous use of mask-like imagery, his 1907 masterpiece Les Demoiselles d’Avignon. The comparison is not a fair one. Both paintings depict women with masks for faces, and both paintings depict those women as a threat to the male artist. But these pieces could not be more different. In the preliminary sketches for d’Avignon, Picasso employs a “peculiar visual pun Picasso… in which the head of a woman supported by a hand can also be read as a torso, with the breasts and vagina displacing the eyes and mouth.” Picasso, in this painting, depicted women who were empowered by their femininity. Gertrude Stein is not empowered by her femininity, she has rejected it. Les Demoiselles d’Avignon depicts female empowerment, but Portrait of Gertrude Stein depicts queer empowerment, making it more forward thinking and socially important than any of the painting that immediately proceeded or succeeded it. It depicts the straight males discomfort with that which is queer, his inability to fit the queer into his worldview, his inability to even connect with it personally. And yet, Stein would go on to call this portrait “the only reproduction of me which is always I, for me.” Portrait of Gertrude Stein not only depicts a strong queer woman; it also depicts the straight masculine world in which that queer woman has made herself strong, rendering it both empowering and honest.

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