Art
10 Masters of the Self-Portrait, from Frida Kahlo to Cindy Sherman
Before the Renaissance, artists were quite shy when it came to selfies. A painter might render a small likeness of himself into the background of a busy group scene, but rarely more than that. It wasn’t until the 15th century, when the German painter Albrecht Dürer began creating detailed images of his face and torso, that became its own genre.
Since then, artists from Rembrandt to Frida Kahlo have made self-portraiture a central theme of their work. “The artists themselves dictate the terms on which we are invited to judge them,” writes artist about the genre in the newly updated edition of the Phaidon tome 500 Self-Portraits. “These are visual autobiographical statements that reflect their times.” Here, we trace the practices of 10 great masters of the self-portrait.

The German Renaissance master was only 13 years old when he drew his first self-portrait. As a 22-year-old, after completing his formal artistic training, he painted himself as a young man on the brink of a revolutionary career in Portrait of the Artist Holding a Thistle (1493). Dürer went on to paint and engrave several more self-portraits through his twenties, nearly all of which show the budding master at a three-quarter angle. With each of these works, the artist seemed to grow more self-assured.
At age 28, Dürer painted his most confident—and his most famous—self-portrait. Posing frontally before a black background, the artist is shown with curled locks that flow over a fur-trimmed coat, which he pulls closed with a particularly meaningful hand gesture: that of Christ’s blessing. Drawing a parallel between the artist and the holy savior, Dürer’s self-portrait is equal parts striking and complex—and it continues to captivate viewers today.

The Mexican artist made dozens of self-portraits from her teenage years onwards, images that have cemented the painter’s face—with her prominent black unibrow, slight mustache, and rosy cheeks and lips—into the cultural consciousness. She often painted herself among the tropical plants and animals of her native country, a nod to her proud Chicana heritage, as in Self-Portrait with Bonito (1941); other times, she is portrayed within simplistic interiors, like Itzcuintli Dog with Me (1938).
Kahlo also used self-portraiture to communicate her suffering. She endured a lifetime of chronic pain as a result of falling victim to a near-fatal bus accident at age 18. works like The Broken Column (1944) convey her anguish: Metal nails puncture the crying artist’s skin, while a column crumbles within her body—a reference to the iron handrail that impaled her nearly 20 years earlier.
In the years since her death in 1954, the rise of “Fridamania” has turned Kahlo’s image into a commercial force; she has appeared on everything from stamps and tote bags to nail polish and household slippers. We’ll never know if Kahlo would have embraced her global celebrity status, but we do know that she wanted to be seen. She left behind over 50 works in which she presented herself exactly as she wanted others to see her: a bold, self-styled, and afflicted artist who championed Mexico’s indigenous cultures.

While primarily known for leaving the imprint of her body in patches of land, a poetic form of self-portraiture, Cuban-American artist Ana Mendieta also created several photographic self-portraits while she was a student in 1972. Her face is visible in these works, but Mendieta distorts, disguises, and otherwise disfigures it, purposely preventing viewers from seeing the artist as she truly is.
For Untitled (Facial Cosmetic Variations), the artist adorned herself with a wig, covered her face with makeup, and pulled a pair of sheer pantyhose over her head. In Untitled (Glass on Body Imprints), she went further, grotesquely altering her features by pressing her face onto panes of plexiglass. The same year, the artist asked a male colleague to cut off his beard; she then glued the hair onto her own face in a gender-bending performance that’s chronicled in the photo series Untitled (Facial Hair Transplant).

The late painter Barkley L. Hendricks, who died last year at age 72, was mostly known for painting full-body portraits of his stylish African-American peers, but he occasionally represented himself in bold, slyly witty self-portraits, which borrow as much from art history as they playfully subvert it. “I was not fascinated with myself as much as Rembrandt or depressed to the extent of van Gogh,” he once said. “However, at times, I could not resist myself as subject.”
An early example is Icon for My Man Superman (Superman never saved any black people—Bobby Seale) (1969). Taking cues from portraiture, Hendricks painted himself (sporting sunglasses and an afro) in the middle of the canvas and facing forward; and in modern fashion, the artist casually crosses his arms over a t-shirt bearing the superhero’s logo. He exudes the kind of nonchalant self-confidence that he was so adept at capturing.
In 1977, Hendricks painted the tongue-in-cheek self-portrait Brilliantly Endowed. Appearing almost fully nude in front of a pitch-black background, Hendricks chews on a toothpick and subtly touches his genitals while standing proudly in contrapposto—referencing the heroic white marbles of and . In another self-portrait from that year, Slick, Hendricks strikes a similar pose in a fully white suit that he pairs with a multicolor kufi cap, a traditional staple of men’s fashion across Africa.

Try to picture the Dutch artist Vincent van Gogh and you’ll likely think of him with a large white bandage over his right ear. This popular mental image of the tortured master stems from Self-Portrait with Bandaged Ear (1889), one of more than 30 self-portraits he painted within a span of only four years.
Before beginning his first self-portraits, van Gogh primarily painted landscapes and interiors, with the occasional portrait of a local townsperson. By 1886, the artist was yearning to develop his skills in portraiture, but lacked the money needed to pay models. So he found a solution: He would paint himself. “If I can manage to paint the colouring of my own head, which is not to be done without some difficulty,” he wrote in 1888, “I shall likewise be able to paint the heads of other good souls, men and women.”
Whether shown sitting or working, and often sporting a straw hat or smoking a pipe, van Gogh painted his red-haired likeness with the pulsating brushstrokes and saturated swirls that characterize his style. Yet after the ear-cutting episode of December 1888, van Gogh created only two self-portraits displaying his injured side—which, because he worked from a mirror reflection, was actually the left side of his face.
The following year, van Gogh stopped making self-portraits altogether, and he died from a self-inflicted gunshot wound in 1890. A full century later, in 1998, his Portrait of the Artist Without his Beard (1889)—which may have been the final time van Gogh painted himself—was purchased at auction for $71.5 million, becoming one of the most expensive self-portraits ever sold.

Cindy Sherman’s hugely influential oeuvre is dominated by the artist’s face—yet none of her works are, in truth, self-portraits. Rather, Sherman uses her body as a vessel or a canvas, bringing hundreds of characters to life in photographs for which she plays both artist and subject, working in front of and behind the lens.
Sherman has assumed the role of this artist-model-actress hybrid since she was a college student in 1975, when she dressed up in costumes and theatrical makeup for photobooth-style shots, anticipating the body of work that propelled her to fame two years later: her “Untitled Film Stills” series (1977–80). Across these 70 black-and-white photos, Sherman takes on dozens of feminine tropes seen in Hollywood films and B-movies alike, from the damsel in distress to the sexualized pin-up girl.
The following decade saw Sherman create two of her best-known photographs: Untitled #153 (1985), where the artist dons a grey wig and stares endlessly into space while laying on a patch of dirt, and Untitled #96 (1981), showing the artist in the guise of a blasé teenager (it notched $3.9 million at auction in 2011, becoming what was then the most expensive photograph ever sold). In the late ’80s, Sherman photographed herself in drag for her “History Portraits” series (1988–90); in one image, she portrayed herself as the Roman wine god Bacchus, à la .
In the 21st century, this inventive chameleon has photographed herself dressed as clowns, fortune tellers, and youth-hungry women who belong on The Real Housewives of Beverly Hills. Indeed, the central tenet of her highly creative practice remains: Cindy Sherman will never take a photo of Cindy Sherman—and if she does, she’ll digitally alter her face beyond the point of recognition, like the freakish “selfies” that have populated the artist’s Instagram since mid-2017. After all, as she once said, “I’m not about revealing myself.”

Pablo Picasso is known for the experimentation and reinvention that characterized his seven-plus-decade career, and in the smattering of self-portraits he left behind, one can witness those transformations: from the romanticized version of his 15-year-old self to the fragmented self-portraits he completed at the age of 90.
Indeed, his earliest Self-Portrait (1896) seems closer to the work of or than what we know best of Picasso’s style. But the dawn of his Blue Period, in 1901, saw the young Picasso’s inventiveness blossom. As is evident in his haunting self-portrait from that year, the 20-year-old had significantly matured over those five years, not just physically (with handsome wisps of facial hair), but artistically, too. Following another six years of creative development, Picasso would make his first self-portraits, rendering his visage in an increasingly geometric manner. Scholars have compared his 1907 self-portrait to the angular faces seen in another work he painted that year, the famous Les Demoiselles d’Avignon.
Few painted self-portraits by Picasso are known to exist from after the year 1907, but the artist drew a handful of images of himself in crayon and pencil during the summer of 1972. One of them may be the most realistic of all: In Self-Portrait Facing Death, the invincible Picasso renders himself looking tired and vulnerable, an artist about to meet his own maker.

Building upon the precedent set by Dürer, the Dutch master Rembrandt van Rijn created self-portraits throughout his prolific career. Indeed, he created nearly 100 renderings of himself from his early days as an artist until the year of his death—including some 40 paintings, 30 etchings, and a handful of drawings. The paintings chronicle his development in a way that’s hardly been paralleled since.
Rembrandt always pictured himself in front of a simple backdrop, and often from the torso up. In his earliest examples from the late 1620s, he is shown with smooth, porcelain skin and voluminous curls, which often partially obscure his face. By the following decade, he favored presenting himself in hats, such as a black velvet cap that appears in more than one of his paintings.
Upon reaching middle age, Rembrandt depicted himself naturally and honestly, with wrinkles and greying hair. This realism extended to the artist’s portrayal of his psychological states: One striking example from 1659, now in Washington, D.C.’s National Gallery of Art, was painted after he suffered major financial losses, the stress of which seems embedded in his face. In 1669, in the months leading up to his death at age 63, he created no less than four self-portraits, compositions in which the aging master appears with thinning silver locks, deep-set eyes, and worn skin.

As a follower of Caravaggio and the daughter of (a successful artist in his own right), Artemisia Gentileschi was the first woman accepted into the Florentine Academy of Design, and one of very few women in 17th-century Italy who had the means and connections to pursue painting. Indeed, imagery of female painters was virtually nonexistent, which makes Gentileschi’s 1638–39 Self-Portrait as the Allegory of Painting all the more significant.
Here, the artist turns herself into the embodiment of painting itself. Based on Cesare Ripa’s visual description of the allegory from his 1593 text Iconologica, Gentileschi portrays herself with disheveled black hair, wearing a gold necklace and shimmering green dress, and holding a brush and palette. She purposely leaves out one symbol traditionally associated with the allegory of painting: a cloth covering her mouth.
Gentileschi refused to keep quiet, even after being raped at age 17 by a painting teacher—a traumatic experience that hurt her reputation and inspired her to create the famous Judith Slaying Holofernes (c. 1620). While the work depicts the titular biblical story, a common subject among artists, Gentileschi inserted herself into her own violent rendition of the scene: she as the raging Judith, her rapist as the beheaded Holofernes.

Andy Warhol used to say that he made self-portraits to “remind [himself] that [he’s] still around.” Indeed, the icon’s image and persona were arguably more central to his work than for any artist that came before him—despite (or due to) being completely contrived. Much like his fellow New Yorker Cindy Sherman, Warhol’s self-portraits revolved around the notion of the self as an artificial construct.
The first of these, from 1963, show the artist in a dime-store photobooth wearing a raincoat and sunglasses, striking theatrical poses like the movie stars he photographed. (These were created at the suggestion of his dealer, Ivan Karp.) By 1966, a new self-portrait, repeated nine times in silkscreen and painted in blocks of color, proclaimed Warhol as a celebrity himself. Yet with his facial features overwhelmed by color and shadow, Warhol is still effectively obscured from the viewer. In his 1981 series of drag self-portraits shot with a Polaroid, Warhol further disguises himself, this time as several made-up, blonde-wig-sporting characters.
But in Warhol’s final self-portraits—shot months before his untimely death in February 1987—the image-obsessed provocateur rids himself of any costumes or alterations, instead appearing starkly natural in Six Self-Portraits (1986). His brightly lit head looks frightened and disembodied against a black abyss behind him, almost like a skull. Like the last self-portraits of Picasso, Warhol appears to be aware of his looming mortality—the reality that in the end, no matter how we fashion ourselves, we are all merely flesh and bone.
Kim Hart