“I actually hate the idea of selfies,” says Cindy Sherman while discussing recent images she has been making with her iPhone. “People say”—she adopts a naive tone—“ ‘Oh, but you’re, like, the queen of selfies,’ ” and then her voice goes flat. “I really kind of cringe at that thought.”

Sherman, who turns 64 in January, has, of course, earned her place as one of today’s great artists by taking photographs in which she almost always appears as the only subject—affecting clowns in elaborate get-ups, self-serious socialites with impressive wardrobes and withering stares, early Hollywood screen stars late in their careers, and plenty of other characters who defy any succinct description.

But the images, she has always maintained, do not depict Sherman herself. “I don’t see it that way, no,” she says. Rather, Sherman exposes how culture shapes appearances, imploding such enforced conformity from within. Since she has long resisted autobiographical readings of her work, it has been intriguing lately to see her take to, and toy with, Instagram, a platform that thrives on interplay of the personal and the artificial, especially when it comes to self-portraiture.

Cindy Sherman

This past summer, Sherman took her private account public, and she has quickly amassed tens of thousands of followers who can now view dramatic sunsets and landscapes, lusciously colored vegetables, and portraits in which she stars that are, by turns, unhinged and uproarious. She began creating these images earlier this year, after a makeup artist who had done her face took a photo with her. “I was so impressed with how he made me look,” she recalls. A week later, though, a friend showed her an app called Facetune, and “I realized that he had actually used this app to just make all of my wrinkles and lines go away,” she says. Sherman now uses Facetune for her own Instagram portraits, as well as two more apps, Perfect365 and YouCam Makeup, to tweak facial features, apply makeup, and toss on accessories.

In Photoshop, which she uses in her artwork, she is able to alter every little detail, but these apps were designed to meet specific needs. “It’s really only about making things prettier,” she says. And yet, Sherman has managed to tease highly unorthodox results—and, often, grotesqueries—from these tools. The women she has created have inflamed skin, warped noses, piercing eyes. Occasionally, identical ghosts burst from their heads or pattern their bodies. Nevertheless, they seem knowable, and lovable, perhaps because of the intimate nature of Instagram or because they have been built with tools that aim to serve desires we can identify. They embody understandable intentions that have gone awry.

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The portraits are not without pathos, in other words, and it seems relevant that Sherman made many of them while convalescing after an injury. “I was kind of just lying around with nothing to do and playing with my phone,” she says, adding that since her recovery, she has had less time to devote to the pursuit, and is beginning to find the experience repetitive. “I feel like I’m looking for something else—another place to take it to.”

Cindy Sherman Cindy Sherman

Sherman’s project for W apes the social media phenomenon known as the plandid—the planned candid photograph, which is “like a newer, hotter version of the selfie on Instagram,” as one social media expert recently put it. They are carefully composed images of studious nonchalance; they capture subjects who are determinedly carefree. Presented here is a mise en abyme of looking: a woman—or should I say women?—posing for herself on her phone as she poses for another photo that she is pretending not to pose for. Perhaps we are seeing the same images that she is viewing on her screen as she tries out different visages on the fly, shuttling through an uncountable number of aesthetic options with taps and glides of her finger. These works have a particular charge at a time when we snap ourselves with the understanding that our image will ricochet onto any number of screens, devices, and platforms. We are all striving to get it right.

Sherman is characteristically humble, almost flip, about her new digital concretions. “All these Instagram images are, for me, just playing around,” she says. “I don’t think it at all competes with my serious work. They’re just fun, like a little distraction.” But while she says that these “silly sketches” have not yet influenced her art directly, she does seem to be enjoying the ease with which these programs function. “I’m not such a perfectionist with using the apps. If you can erase the background and add another background, I don’t really care if the edges are all clean, and if it looks kind of funky, or if things overlap in a not-so-perfect way. It’s kind of freeing me up a little bit and maybe making me more open to experimentation.”

Originally, Sherman planned to work from different photographs for this piece, but after completing the first, she said to herself, “You know, let’s see if I can make the same image completely different, because it’s so easy to do with the app.” By taking a single photo and running it through a series of algorithms, conjuring an array of images from one source, she is indulging a process that is central to an era when surface-level identity and truth can seem variegated and unmoored—a reality at once disorienting, disturbing, and, in the right hands, deeply thrilling.

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