Close Friends
With Artist
Caitlin Cherry
On Painting The Optics And Illuminations Of Women’s Work
- Text: Osman Can Yerebakan

Caitlin Cherry is a painter of cyber-multitudes. Her models pose in gestures reminiscent of art history, but they emerge from gnarly squares of social media: she paints Black women based on their Instagram posts, abstractions of nocturnal colors, and forms inspired by software codes. The sharp tones of blue, purple, green, and yellow convey a sense of metallicity in her brushstrokes; the canvas appears malleable and chromatic, much similar to a computer screen. The subjects are influencers, as well as occasional dancers, bartenders, or models—the painter works against that evanescence of woman’s work.
Cherry’s most recent exhibition, Crichoues Indignation, ran at New York’s The Hole gallery in the fall of 2020. Through her electric paintings of Black femmes drenched in psychedelic abstractions, the viewers reached a sleek structure, a vault-like form with two enormous fans on the side, like something out of a 90s music video. Each of its five modules stored another painting available to those who typed the exclusive passcode onto the storage’s keypad. Once entered, the combination would unleash the railings, and the art would reveal itself.

Caitlin Cherry, Boyfriend #2, 2020. Oil on canvas, 58 x 105 inches. Image courtesy of the artist and The Hole NYC.
Cherry had limited the knowledge of the code to those added to her “close friends” on Instagram. The artist’s offerings, however, were not what the lucky few fully expected either. The first slot had a neon pink-hued underpainting with a medley of orbit shapes and faint illustrations of women. “A vulnerable painting,” as Cherry calls it when we first talk, “was something I would only let my close friends see, because it was incomplete.”
The New York-based artist named her The Hole exhibition after a Kanye West tweet in which he misspelled the word “righteous indignation” in a moment of fury (the tweet was a thread in a thread of conspiracies about his public image). “I am interested in the typo in terms of its algorithm problems,” says Cherry. “He must have typed it so incorrectly that the smartphone could not recognize and fix it to the actual word, but this is a universal problem: we are expecting these machines and algorithms to actually do a lot of work on our behalf.”
Cherry’s work encapsulates the cultural moment between the real and the digital—the complete and glitched. Within this harmony of chaos, she questions how Black femme bodies endure. Their existence is particularly precarious on the web, where they are heavily claimed as one-liner memes and hyper-sexualized objects. Cherry looks at value as both an abstract and tangible notion in her paintings: the bodies assessed by hits, likes, and comments, surrounded by software.
With her eight-year-old Canadian Sphynx cat Chanticleer on one side, Cherry sat down for a Zoom interview about painting Black women, the aesthetic of algorithms, and the beauty of the moiré effect.
Osman Can Yerebakan
Caitlin Cherry
Your Instagram profile says “Gamer,” as opposed to “Artist” or “Painter.”
I am very much interested in sci-fi and action movies. In terms of gaming, more than a player myself, I am an observer. I watch the reactions of people playing games on YouTube. As a painter, I am archiving all these interactions between us and the machine.
How has your relationship to the internet and online culture changed during the pandemic?
My work has always contained this debate between our real selves and digital selves, but this shift from IRL to URL has been a little jarring. Suddenly, my artwork has to be viewed online, I have to teach online, meetings are exclusively online.
I’ve been sensitive to the ways a painting circulates in an institution or in the market; A lot of my paintings get acquired before the collector sees the work in person. When I did an online show with my Los Angeles gallery in June, the experience didn’t feel very different than a real-life exhibition on my end, because I was already aware of this disconnect between how the work is made, exhibited, and eventually collected.

Installation View, "Crichoues Indignation". Courtesy of The Hole.
Cherry’s work encapsulates the cultural moment between the real and the digital, the off and online, the complete and glitched.
What do you think about anonymity of the digital realm? Social media can be about being anonymous as much as it is about self-expression. Do you think that’s true of art as well?
I personally have a certain way of interacting with content on social media. I pick my models there, but I only screenshot the post I’d like to paint. I don’t engage through comments, “likes,” or DMs. In that sense, I remain anonymous, too. In terms of artistic visibility, I present myself and my work on social media and my artwork; this can sometimes include hyper-presentation of myself, as well.
Sometimes I hear people complain about how people do not post their “real selves” on social media. That realness conversation is uninteresting to me, because I am not somebody who believes in some sort of singular personality or representation of the self. Black women have to navigate the world where there are a lot of miscalculations and stereotypes about who they or their selves are. The digital realm and social media can really further this miscalculation, as much as it can help them to express themselves.
In that sense, let’s talk about the way Black women are used for memes. How does this reality inform your research on social media?
There are critics who talk deeply about this subject—such as Aria Dean who wrote a great essay called “Poor Meme, Rich Meme”, or Legacy Russell who just released a book called Glitch Feminism: A Manifesto—but I can talk from my own experience. As a meme user myself, I see people express their emotions within this mass syndrome of not being able to fully express themselves. Instead, they choose this version of a black face. They project Black women as their “emoters”—it’s almost like a horror movie in which they want to use that skin to be in. In reality, Black women are not allowed to be the way they’re portrayed in those memes, and this also commonly happens to the Black queer folks. Of course they’re never compensated for that.
Do you see a parallel between art history’s depiction of the woman figure, either as a Mary or a Magdalene, and the way social media represents Black women, who have historically been kept outside of art history?
I think about the immediacy of representation. An influencer can post their image today, I could have it as an underpainting by Sunday, and the painting could get done in two weeks. This quick cannibalization of the image into a painting means encapsulating something that would otherwise be a fleeting post.
My intention is to archive this process. Our history gets discarded really quickly, and our actual impact on popular culture is forgotten.
These women are the Magdalenes—hyper-sexualized or hyper-visible for a moment. Their work is not valued, and very few of them reach that level of becoming somebody like Cardi B. Not many people recognize that some of the most popular beauty trends and cultural moments are coming from Black and Brown strip clubs. I identify with them because of how I look and how I move through the world.

Installation View, "Crichoues Indignation". Courtesy of The Hole.
Your visual language blends bodies and digital codes. I see a connection there between abstraction and figuration, both literally and conceptually.
This goes back to the difference between viewing the painting in person or online, where the patterns and bodies convey different layers and textures. My figures are not sitters posing on chairs or lounging on sofas; the digital realm inherently lacks context to begin with—everything is in snippets sliced out of life. I construct my paintings in the same way. You see multiple women collaged from different social media posts, but in reality, they never existed or posed in the same room. My paintings circulate online through Instagram or websites, so they exist in codes even more than they physically exist in canvas and paint.
I mash these two worlds: figuration of the bodies and abstraction of codes on top of each other. The hardware and the software blend together. The distortion of colors creates a solarized moiré shaded with bands of light, which may seem tricky to the eye. I also think about how the image is protected through CAPTCHA tests or watermarks, which have their own aesthetic. I apply this question of protecting an image or limiting its viewing, similar to a watermark or the “I am not a robot” test.
In this vein, a painting can inhabit all these realms. There is the painting, there is the JPEG or TIFF version which I download, and there is another abstract version, which lives on a zip file, Dropbox or iCloud.
I try to make paintings that trick the camera, so viewing a painting in person still promises a different experience, but very few people actually see a painting. It has such a longer life as an image beyond its physicality. Even when the work travels museums around the world, it still reaches a limited audience. This is also why I am not bothered by the idea of an online show. It was going to end up there anyway, and I don’t subscribe to that idea of a painting losing value when viewed online. The majority of people will not see your work in person due to socioeconomic circumstances that prevent them.
Does the photographic quality or style of your source material influence your decision over the canvas?
Digital cameras, which produce most of the images I base my paintings from, have a focus point. Think about how you snap a picture on your iPhone—you tap onto the screen to determine a focal point. I think the paintings confuse the camera’s focusing system and add another layer of transformation. If you are viewing my painting in person, you are more likely to see the women first. If you look at its photo taken from any distance, you see the waves more prominently. This duality maybe wasn’t intentional, but this moiré pattern is its own security feature of the painting.
The iridescent effect cannot register until the viewer starts moving, so here is that static element. Achieving that visual quality took some time, which included experimenting with my palette. The metaphor of liquid is a concept I can tie to natural references of the world, such as screens, which are made out of a type of liquid crystal materials. But yes, that flow is always in my head: the flow of money, of colors, of light…In my own way, I’m controlling its appearance online.
Osman Can Yerebakan is an art writer and curator based in New York. His writing has appeared on T: The New York Times Style Magazine, The Paris Review, New York Magazine, The Guardian, Brooklyn Rail, BOMB, Artforum, Artnet, Playboy, and elsewhere. Osman previously organized exhibitions at venues that include the Queens Museum.
- Text: Osman Can Yerebakan
- Date: January 19th, 2021