When I visited the studio of painter Pieter Schoolwerth this spring he showed me a diagram he’d made to visualize his position in the history of painting. If cubism depicts one object from disparate perspectives, his art expresses a single perspective dispersed across multiple objects. It’s about the experience of giving attention to the multiple tabs, apps, and posts that clamor for it—the passive activity of reading a feed that immerses you. 

Schoolwerth’s diagram dramatically simplifies the contrast between cubism and whatever you might call what he’s doing. It elides some very complex processes happening under the surface. To render the multiplicity of modern subjectivity, cubists reinvented painting from the ground out. They segmented the canvas in ways it had never been segmented before. They dabbled in compositions and perspectives alien to European painting. These days Schoolwerth and other artists who aspire to convey contemporary subjectivity through painting are once again reinventing the preparatory work of their medium. They’re not just translating the textures of digital media to physical ones; they’re putting the conditions of digital image environments in dialogue with centuries-deep traditions of constructing the painterly image. 

Painting is a baggy monster. Just as a contemporary novel might incorporate the language of comics or emails, so has painting promiscuously absorbed other, more recent mediums and communicative techniques. This phenomenon is not always an enriching one. Stroll through an art fair these days, and you’ll see dozens of paintings that simply reproduce the straightforward gaze of the camera. But there are other ways in which painting has reckoned with strategies of reproducibility that open the medium to new possibilities and problems—the silkscreen paintings of Andy Warhol and Laura Owens, Audrey Flack’s paintings of overhead projections, Jasper Johns’s paintings that incorporate stencils and potato prints. 

Software is now ubiquitous in the painter’s studio and life. Some painters emulate and parody Photoshop’s tools. The best such work evokes the weird limbo of digital art, where phantoms of old media are summoned as templates and patterns. Image-making software shortcuts laborious processes. Studio training gets subbed out for tutorials. Painting becomes odorless and nontoxic, offering itself up as a swipe of the mouse. Some painters use these shortcuts in a new kind of preparatory work that replaces drawings and etudes, organizing the painting in ProCreate before committing it to canvas. This sometimes has a flattening effect, making paintings that look great on Instagram because they were conceived from the outset as digital images. They don’t push past the modes of composition and layering that are readily available in the program. They are paintings by expert users of software.  

Artists are more than users when they play with inputs and outputs, taking a file made with one program and remaking it in another, intervening by hand with physical mediums at some point (or several points) in the process, and otherwise making short circuits and wayward paths where the software functions as one tool in the studio rather than a substitute for the studio itself. These exploit the speed of digital media but also slow it down, mixing the ephemeral temporality of digital images with the long duration of the painted image that is made to be looked at again and again over time. They return to painting’s historic foundations in order to make work that speaks to psychological and social effects of digital media’s present.

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The head of the Farnese Hercules glows amid a morass of half-formed images in Andrew Woolbright’s The day you told me I was like a [vandal] (2021). It’s lined in cyan, with a jaundiced wash of neon yellow. The vibrant, lucid tones of a backlit monitor, rendered with the substance of acrylic paint, give the antique head an uncanny embodiment. Elsewhere in the painting’s pale blue cloud you can glimpse tongues and eyes, but nothing coheres into a face. These are textures without objects. 

Woolbright’s atmospheric paintings guide the viewer’s gaze from top to bottom or left to right, never offering a center where it might rest. The effect re-creates the eye’s sliding movement over digital pages. His underpainting builds cellular structures that the images on the painting’s surface seem to slip through, like media passing through the boxy windows and tabs that organize the screen. Other paintings from the same body as work as The day you told me I was like a [vandal] mix the iconography of medieval Christian art with emojis and memes, collapsing expressive visual language from different eras. Logos of long-shuttered software companies appear like fragments of rigid banner ads, stuck in the goo. In Woolbright’s more recent work it has become harder to discern any direct references. In Bobby Venmo gets a William Blake tattoo from Jamiroquai (2024), a form that could be a splice of the Firefox and Twitter logos swims in the half-scaffolded haze. This is a painting of the associative links that the mind shifts through as it encounters informational sludge, tries to make sense of it, and barely does. 

Glitches are artifacts of technology’s shortcomings, a machine’s failure to execute its functions as intended. The artificial modeling of glitches in art often functions as a metaphor for the discrepancy between the real and the ideal, and points to technology’s role in revealing these gaps. In his early work, Chris Dorland invented a series of painterly techniques to imitate the glitchy negative space of photocopies and scans, rendering by hand the frayed edges of the images produced by those machines. 

Dorland’s recent bodies of work about the space of the computer screen still exercise technical prowess to reflect on machine-made images. But in these paintings the screen doesn’t look glitched so much as utterly destroyed, collapsed under the weight of its many iterations over time. The riffled striations that characterize these paintings both evoke the movement of light through an LED screen and the streaking of ink in a jammed printer; their textures shimmer between material and effect. The content of his paintings comes from screenshots of his desktop, arrangements of icons and code in action, layered digitally and then physically in a play of inputs and outputs. In several works, a film of UV coating laid over the surface bunches and ripples like skin. Dorland’s working over of the surface makes the immaterial recesses of digital space feel visceral. 

Dorland and Woolbright both overlay moments in one overall image, compressing the screen’s varied appearance on a single plane, where hazes and goos express both time stretching out and the mess of apprehending it all at once. Schoolwerth, too, foreshortens the temporal experience of digital media. His “Rigged” series (2022) assembles 3D models purchased in marketplaces largely used by fan artists, video game designers, and architecture interns charged with populating mockups; these are paintings about online impulse shopping. The scenarios deicted in the works vaguely recall classical academic painting, but are too twisted to line up with any known myth. The Architect of Wheelbarrow Park (Rigged #22), 2022, loosely outlines a scene of seduction, but it takes place in a suburban yard. The seducer has a translucent torso and a pink brushstroke for an arm; the prey languishes in a wheelbarrow, one limb careering upward and growing into a grinning Kim Kardashian. Their love triangle is complicated by other ghosts and shadows who haunt the space between house and fence, triangulating the mythic, the supernatural, and the banal. Encountering this overstuffed tableau, the gaze gets split into multiple directions at once, struggling to make it all cohere.

Each figure in “Rigged” comes with its own aura, the trappings of the genre it was designed for, be that an airline ad or a horror game. Schoolwerth picks up models made at different times—2003, 2010, 2018—and each is marked by the textures and levels of definition available to its creator. They’re also modular. The title of this body of work refers to the “rigging,” the 3D model’s skeletal figure that bears its surface textures. When put together as intended, the hair texture goes on the head and clothing textures clad the body. But Schoolwerth sometimes shifts the surfaces across the rigging, or puts the skin of one model on another’s skeleton, to achieve smearing, warping effects. 

Schoolwerth has always been fascinated with Baroque maximalism, and he seems to delight in the mistakes of its mediocre examples, where figures compiled from sketches and etudes don’t quite fit, their gazes and gestures misdirected if they don’t quite occupy the same space. Schoolwerth has addressed the history of academic painting in various ways over the years, breaking it down to component parts. His 2010 series “Portraits of Paintings” compiled tracings of figures from classical painting as models of the fragmented contemporary subject. In “Model as Painting” (2017), he revisited the practice of making shadowbox models by carving compositions in foamcore, then scanning them in Photoshop, to create absences and layers in software that were informed by their physical residue. In “Rigged,” Schoolwerth treats classical compositions as a kind of rigging, and the figures in them as the skin. Just as he does with the models themselves, he warps and warps these rigs to achieve effects of excess and disarray. Whereas Woolbright creates new structures of underpainting and populates them using painterly techniques, Schoolwerth adapts the rigging of classical painting to digital media and uses the capabilities of software to stretch it and remake it; Dorland experiments with both structure and technique, seeing what happens to the format of painting when its tools are integrated with—or swapped out for—the computer’s peripherals and the iterative processes of software.

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I’ve been fortunate to have access to the studios and time of Schoolwerth, Dorland, and Woolbright in recent months, and that’s why they’re the artists I write about here. But there are others whose work stages dialogues between the foundations of painting and the possibilities of digital media. Caitlin Cherry re-creates thirst traps found online with wild palettes and goopy textures. Her paintings look great when the images return transformed to Instagram, but reward in-person study, too, with the richness of color and compositions that foreground the conventions of painterly portraiture that persist in social photography. Austin Lee’s early work reverse-engineered the look of painting programs for the iPad, using spray cans to simulate the hazy halo of the simulated brush. He still dips into the feedback loop of paint, the digital rendering of paint, and the physical rendering of digital paint. Avery Singer uses a robotic apparatus to apply paint to canvases, realizing software-made compositions that splice the conventions of constructing space in digital and painterly environments. 

Not all artists who use both paint and digital media do so in ways that rework the process of painting. Amy Sillman is a great painter who also makes drawings and animations on her iPad, transposing the action painter’s gestures to the touch-screen’s haptics. As far as I can tell, the connection ends there; I can’t see any software-based tools or procedures working their way into her paintings. Simon Denny’s “Metaverse Landscapes” depict bird’s-eye views of virtual plots of land, drawing attention to the segmentation and trade of digital space. Denny doesn’t engage with the history of painting in formal terms so much as socioeconomic ones, alluding to the role of landscape painting in colonization as a mode of presenting unpopulated vistas to be conquered and monetized. His “landscapes” are interesting not as paintings but as conceptual objects that use painting for its historical associations.

Denny’s work fits neatly in a way of thinking about contemporary painting that has dominated art-historical circles since David Joselit’s influential 2009 essay “Painting Beside Itself,” which argued that paintings of our time operate as objects that refer to the networks in which they circulate. I think Joselit’s theory is useful, but I also suspect it compounds the flattening effects of the mediating networks he describes. When a painting is understood first and foremost as an object, it becomes harder to see it as a painting. In other words, this line of interpretation doesn’t always take into account the inner languages of painting, the complexities of its means of constructing an image that set painting apart from other kinds of objects. 

The artists I discuss here are thinking deeply about the condition of the image in contemporary media environment. But they’re also committed to painting as a medium. They’re engaging with its preparatory processes—underpainting, sketching, and the structures of a composition. They’re not approaching these concepts with nostalgia. Instead, they recognize these strategies as the root of painting’s persistent capacity to express a model of a subject. 

Brian Droitcour is an art critic and the Editor-In-Chief of Outland.