ArtFebruary 2026In Conversation

ROB PRUITT with Andrew Woolbright

Portrait of Rob Pruitt, pencil on paper by Phong H. Bui.

Portrait of Rob Pruitt, pencil on paper by Phong H. Bui.

Skyscapes
January 15–March 7, 2026
303 Gallery
New York

The artist Rob Pruitt began making work as a rebellious art student in the mid-eighties, beginning a professionally successful, albeit brief, collaboration with his then-partner Jack Early, lasting into the early nineties. Together the two made sculptures and paintings that in turn interrogated and showcased the masculinity which had policed and persecuted them each throughout young adulthood. After a controversial exhibition and a subsequent hiatus from the art world, Pruitt returned solo in 1998 with Cocaine Buffet—a 16-foot-long mirror laid flat on the floor of the exhibition space with a coordinating 16-foot-long line of cocaine down the middle, which visitors had to kneel to partake in. Since then, his career has run the gamut from daily portraits of Obama to his trademark panda paintings. The artist spoke with Rail Editor-at-Large Andrew Woolbright to discuss his latest exhibition at 303 Gallery—a series of spectral watercolor gradients that deal in time past and passing, constantly in flux. The exhibition opened on January 15, titled Skyscapes. When the gallery opened its doors on Friday, January 16, it was then called A Bird in the Sky—the artist has promised to update the title every day for its duration.

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Rob Pruitt, October 28, 2025 (24 Hours) (Potomac River View), 2025. Signed, dated, titled verso. Acrylic on canvas in hand-painted artist frames, 24 parts; 83 3/4 x 67 1/4 inches overall. © the artist. Courtesy 303 Gallery, New York. Photo: Justin Craun.

Andrew Woolbright (Rail): Someone was telling me that they went to school with you when you were an undergrad, and they said that there was a drawing assignment, and you came back with a green piece of paper that was a poem about salad and lettuce.

Rob Pruitt: [Laughs] It definitely sounds like me. I mean, clearly it’s making me laugh. Yeah, I think as a student I was a strange mix of overconfident and lazy. I was just feeling so excited about having moved away from suburban Maryland to the epicenter of the world, New York City. And I just had this definite idea that I couldn’t be taught anything in a class that I couldn’t learn better out on the streets of the city.

I do remember a work from that period that is similar for a sculpture class. I bought several boxes of Ziploc baggies and filled them a quarter-way with water, and then taped many, many bags to the wall of the critique room and presented it as a sculpture, called Tidal Wave.

Rail: [Laughing] On a budget.

Pruitt: A supermarket budget. Exactly.

Rail: How can you create a natural event by just going down to the grocery store? You went to school in the early eighties. And early on you’re getting into a post-Warholian practice. There’s something about an elevated prank at work here, or trying to get the most out of the least amount of effort. It seems to start with “Sculptures and Paintings for High School Boys.”

Pruitt: Well, you’re close to the title. The umbrella title is “Artworks for Teenage Boys.” And then there were “Paintings for Teenage Boys,” made out of commercially produced beer logo fabrics and T-shirt iron-ons. So each image was a mash-up of the beer fabric, and then whatever random T-shirt iron-on that we put dead center. And then the sculptures were called “Sculptures for Teenage Boys.”

Jack Early and I were both from suburban backgrounds—myself right outside of DC, and he was from North Carolina. We had come together at art school, and it was so liberating. It was the very early eighties, and culture and society hadn’t caught up to where we are now. So having never gone to a dance or freely expressed affection like all the other kids in class were free to do, this was something brand new. There were other more complicated things to contend with too, like the psychological trauma of getting beaten up and picked on. So there was this great release and freedom from meeting and developing a relationship and having sex, like, practically from the first day that art school begins. So that was the circumstance of how Jack Early and I met, and then we stayed together. We actually got together early in art school and then split off and went to different schools, and then resumed our relationship and met back in New York and started collaborating. I always thought of the collaboration as a union that was like our version of marriage—at least to the public. You know, it’s like, “We may not be able to get married, but we can make these projects together, and stick our names together in a way that’s a declaration, a very public declaration, of love and togetherness.” So it was kind of a political act.

That work was about creating a portrait of the enemy, as we knew it, thus far in our young lives. We wanted to make work about the boys that would pick on us in school, who were fostered by a culture to be dominant. So we would use these stickers and T-shirt iron-ons from boardwalk shops and head shops and record shops that promoted this kind of male aggression and misogyny, and try to flesh it out to see who this über-male creature is that culture so wants to participate in creating. That is our arch enemy as two young gay guys in 1987 or ’88—that’s the moment we were making it.

But maybe it wasn’t didactic enough. I can remember at one point Stuart Regen, Barbara Gladstone's son, invited us to do a show, and when he picked us up at LAX, I think he had a cooler of beers in the back of his Jeep and he was blasting Lynyrd Skynyrd. I think he was expecting to pick up the dudes the show was critiquing. And of course, we were our own gay versions of hell-raisers, but we certainly didn’t believe in the stuff we hung on the walls. I was strongly influenced by Jenny Holzer and Barbara Kruger, and I loved the potent negativity in these redneck T-shirts and stickers that was so antithetical to their language. But I thought that that was the juice of it. I mean, these absolutely obscene messages and mottos—I just thought, “This stuff directs the culture.” And it was important for somebody to rake it all up and, like, save it for posterity.

And so the sculptures were made out of putting stickers on beer cans and then stacking up the beer cans. The beer is a mass produced, grocery store commodity, so it already has this direct relationship to Minimalism—like Carl Andre, like squares on the floor, repetition and uniformity, and, you know, sequence and endless supply, right? And so once we stuck one of these teenage stickers to each beer can, we then used those as units to construct sculptures that had so much to do with the legacy of Minimal art. It was a wrap, in a way. There was no more. The project kind of just emerged, like, fully formed out of the simplicity of the mash-up of something from high art and the lowest possible cultural element. And then the paintings were the same way. We used that same beer math. Each painting was presented in a six pack—six panels—or a case—twenty-four panels—and then a T-shirt in the center of each panel, and a T-shirt iron-on.

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Rob Pruitt, January Sunrises, 2025. Watercolor and silkscreen ink on watercolor paper, 31 ¼ x 48 inches paper. © the artist. Courtesy 303 Gallery, New York. Photo: Justin Craun.

Rail: This gets us to how you’re reframing the ordinary, and you’re using comedy to reframe it. Comedy is a slippage of expectations, and reveals how little it takes to lose control of those standards. It seems like it’s a consistent theme of yours—a recognition that the ordinary is where politics reside, which, in this case, frames macho and aggressive masculinity as an ordinary.

Pruitt: In my case, it was highly personal, too, because I had felt othered by culture, even attacked by it, and so it was convenient to create an autobiography through these things rather than through an essay.

Rail: And to do that, you’re speaking in a tongue that’s not yours—a different dialect to try to address the culture that pushes your experience to the margin. I really like this phrase you used, “portrait of the enemy.” Has that continued on in your work?

Pruitt: Well, after Donald Trump was inaugurated for the first time, I did a group of paintings that were shown at Gavin Brown’s enterprise, at the Harlem location, that were based on the traditions of American quilting. There’s a kind of timeless legibility in the history of American quilts. Geometric patterns have a narrative. They’re not just about design—the geometry means something. And so I took some of that language and that history and tried to express the hate that I thought Trump was bringing. Well, not just the hate, but also how it came to be that he could seize the highest office in the land. And I think I came up with like five or six stories to tell, using the history of American quilting. It was very much a similar equation or system to the teenage boys artworks, right? So I cut pieces of steel and dipped them in acid to acquire different levels of rust to make this connection to the disenchanted blue-collar steel worker that was attracted to Trump, because they were being promised that the factories that would never come back, would in fact come back. And I made a big quilt version of the American flag—which is essentially a quilt in-and-of-itself—out of red-, white-, and blue-tipped wooden matches. With the igniting of one corner, the whole thing would immediately go up in flames. I don’t know how much more I can go on about that project without actually reviewing it by itself. It was kind of like a capsule project, because this was a moment in time when I could see the country taking a sharp right-hand turn, and it just didn’t make sense to make another panda show.

Rail: Well you utilize immediacy so well. You often are stepping into the stream of—whatever you want to call it—history or time, and trying to say something about it before it’s fully formed, knowing that it will change context. And then you work with materials and objects that are camouflaged to us—mass produced objects of the ordinary.

Pruitt: There’s such a value, I think, in acting immediately rather than waiting, and then presenting a version of the evidence of the outcome, right?

Rail: The alternative is the essay you’re trying to avoid. How familiar or close are the pandas to you?

Pruitt: Extremely familiar. Extremely.

Rail: Can you elaborate?

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Rob Pruitt, Bright Light - Purple, 12/7/25 (Gina), 2025. Acrylic on linen, 108 x 81 inches. © the artist. Courtesy 303 Gallery, New York. Photo: Justin Craun.

Pruitt: Well, I had reached a part of my career where there was no career. That early part when I was collaborating with Jack Early had been wildly successful. And then all of a sudden, there was no career. We made a catastrophic misstep of an exhibition that got blasted in the press. We were young, and the relationship wasn’t just professional, but romantic. And it just didn’t bear the pressure of that. So I had to think about reinventing myself during this postmodern age of Madonna; this notion of reinvention had entered the public consciousness because of her. Finding myself in this dilemma, I started making some work on my own, and had the people that had helped us initially come back for studio visits, and a lot of them were like, “It’s really interesting. Maybe it’s as good or more interesting than the previous work, but your name just doesn’t have the same value anymore. You kind of ruined your name.”

And that early solo work was about recycling, really. I think we divided stuff at that point, and I had some leftover Pruitt-Early work. And I was just trying to use it the way a folk artist might find an old car fender on the side of the road, and turn it into something. I was thinking, “I’ll just use these as building blocks and recycle them into something new, by painting over top of them and nailing things to them and stuff like that.” So I remember I had this idea that I would use some of this early stuff, cut two holes in the plate glass window of 303 Gallery, and ask people to put their paper trash in one of the holes and their metal trash in the other hole. Then I would sit in the front room of 303, which had moved to Chelsea at that point, and use that stuff that was being given to me along with the older Pruitt-Early stuff to make assemblages for the thirty days of the show. This was in 1997.

Rail: I think it’s really interesting to publicly recycle your own work. I feel like I can think of some artists that did that much later. But it’s a real addition of yours to how we think about what art is. Artists have always reworked things, but for you to publicly perform it makes it into something like packing up the county fair at the end of the summer.

Pruitt: I really do like to think about all my new work as a kind of recycling: from the beginning of the day and career to the end, and then over again. And all delivered with humor, because in my real life, I’m not a confrontational person; I’m a coward. So the comedy is a nice device, because it’s confrontational, because it is asking you whether or not you think it’s funny. Like, you have to laugh or you don’t have to laugh. If I say, “Look at that tree. It’s beautiful,” you don’t really have to respond or participate in that. But if I give you a joke, there’s a demand on you.

Rail: Lauren Berlant talks about the relationship of comedy to sex, and the connection is that both are always bumping up against ethics. Choosing to laugh at the bad joke or not creates the inside-group, but then also, like sex, it always bumps up against subconscious desires and threats. We recognize it for the intention it subverts. Berlant says, “The failure of the body to respond to intention is at the heart of physical comedy.” And then she describes “the slapstick of ordinary relation”—two people trying to build something that neither one can build on their own. But even more relevant to you is that she also spoke about humorlessness, and how since Trump’s inauguration, we’re in a world where everything feels like comedy, but there’s no joke. Everything feels like there’s going to be a punchline because it mimics the form of ridiculous delivery.

Pruitt: It feels exactly like that—like an endless stream of punch lines without the jokes. We don’t know what the jokes were, but we see this big pile of stupid punch lines.

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Rob Pruitt, Karen, 2025. Oil paint on concrete, 16 ¼ x 8 ¼ x 9 ¼ inches. © the artist. Courtesy 303 Gallery, New York. Photo: Justin Craun.

Rail: To your point, you use humor as that slapstick of relations, in that you’re always looking for someone else to build something with. And when they don’t get the joke, that’s powerful too—it creates a totally different kind of thing that asks, “Who gets to dictate and say what the ordinary is?”

Pruitt: The panda paintings came about, at least for me, with the rhythm of a joke. That subject matter just arbitrarily changed the direction of my art making production in the silliest of ways, but it was practical too. I wanted to solve this problem of—having been invited to the party and then being shut out of the party—how do I get back in? I was from DC, and I really loved the pandas that had been given from China to the US in the early seventies, when I would have been about ten years old, and I was thinking about how they are kind of endangered and kind of like a Christ figure. And then I just also thought, “If I align myself with this panda bear as an avatar… everyone loves a panda bear.” It’s sort of like most people’s first toy before they can even walk or speak.

Rail: So the panda is redemptive.

Pruitt: But isn’t it amazing that there are other endangered species that the world doesn’t gather around and root for?

Rail: Well, cuteness elicits a pleasure in us—to see something more vulnerable than us. And pandas can’t care for themselves. Is there work that you make, other than the pandas, that feels vulnerable, or maybe that you’d even consider to be bad in some way?

Pruitt: Maybe the paintings that come up to auction? I always assume they are the worst paintings. Nobody can find enough love for them to keep them, right? My mother was a hoarder, and part of me too can’t let go of the unneeded things—even bad paintings. Even if I could buy the bad paintings back to save my own market, I wouldn’t be able to destroy them. I think I would need to invent a new project, like paint them all yellow or something. “These yellow paintings aren’t the bad paintings anymore, they’re perfectly new and fresh and ready for you to buy and love.”

Rail: It’s a really funny idea. Another panda, or another redemption through humor.

Pruitt: But there’s some kind of mental illness there, where I do have the desire to retract it, but then I can’t get rid of it.

Rail: Knowing you’re against cliches and the more romantic notions of being an artist: What is it that you are committed to? What are the rules you have and won’t break? Maybe one is the inability to destroy something. Are there others?

Pruitt: It’s such a good question. I know that I’m committed to work. I just come to this place every day, you know—ten until six, if not longer. I feel like if I were to miss a day, the whole thing would just collapse. I don’t know why I have that paranoia. I think I’m a modern person in that I was born in the mid-sixties, knew that I was gay, knew that I didn’t want to keep it private, and knew that I wanted to be as political as I could possibly be without actually being an activist—not that there’s anything wrong with being an activist, but I’m not terribly confrontational. I just knew that I didn’t want to keep any secrets about myself, and so I’ve always used art making as—I’m going to use a term for something that I don’t really even know all that much about—art therapy. Like, I use all these projects to figure out where I am at any given moment. But conversely, if I were approached by a gallery with a proposal to do a show outside my own set of ideas, I’d say yes immediately and figure it out tomorrow. I mean, I follow an organic path, but I love opportunity.

Rail: That doesn’t strike me as a contradiction though. It strikes me more as you seeing art closer to improv or standup, or you being interested in this charismatic relationality that can occur.

Pruitt: I do love that. I love to think about improvisational jazz musicians or improvisational comedians. I like having to think on my feet. The period of time that I worked with Gavin Brown maybe fostered that in me, because I think he was kind of a hidden collaborator with each of his artists. I don’t want to speak for him, but at least in my case, you know, he would say, “I have something in mind for the Art Basel booth, and even though it’s in, like, four weeks from now, do you think that you could come up with this type of project?” And I loved getting those challenges from him that a lot of artists might not say yes to, because there’s a thrill in the possibility of not succeeding.

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Rob Pruitt, Let’s Start This Day Again (After Ugo Rondinone) (detail), 2025. Acrylic on vintage clocks, clock movements; 12 panels, 25 inches diameter. © the artist. Courtesy 303 Gallery, New York. Photo: Justin Craun.

Rail: That’s interesting. Can we talk about Cocaine Buffet (1998)? I wonder if there is maybe a consistency or a commitment within your work. Maybe the work’s crux is this real anger or rage or wrestling with the concept of repression—both the idea of cultural repression and personal repression. Your work seems to always want to unrepress or desublimate something. And Cocaine Buffet is so direct: it’s the thing everyone wants in the room, but they don’t want to give it to themselves or allow themselves to have it.

Pruitt: I’m definitely interested in the angle that you’re coming to the piece with. But for me, cocaine gives you a false sense of focus. It’s absolutely a release from repression, but that’s any buffet in some way. It’s a bacchanalian feast. I’m interested in the invitation. I like to mess with an audience member that way, to either present them with excess or to deprive them. In retrospect, formally, I was really thinking about Barry Le Va’s blown chalk. And I thought, “I can wear this work to a costume party.” But there’s a little act of revenge in that cocaine piece, towards all of the people that were not nice to me for a couple of years. I may have deserved being blocked out, but I wanted to bring these people to their knees by dangling something in front of them that they would not say no to. But there’s a metaphor to art with cocaine. You get a jolt of euphoria that maybe is what people are always hoping to get from the art that they relate to the most, or the art that they think is best, when looking could become physiological. So it’s perverse to make an artwork that isn’t just gonna send shivers up metaphorically, but literally, and I’m interested in this because it’s absolutely cheating. I think I was wrongly blocked out of the nineties Relational aesthetics movement, don’t you? Wait—you don’t have to answer that.

Rail: It really does function like comedy. Your lack of inclusion exposes a type of repressed ideology or a type of structure, like the idea that I haven’t thought of Cocaine Buffet as a work of Relational aesthetics, and people typically don’t. Maybe it reveals this idea of ethics or utopic positivism attached to the movement.

Pruitt: Well, it may be operating parallel to it. It definitely reeks of me and my interest. An influence for me is somebody like Robert Isabell, who was foremost a party planner and florist. You hear folktales now about Studio 54, and how on her birthday in 1977, Bianca Jagger rode around on a white horse led by a naked man painted into a tuxedo, as confetti fell from the ceiling. And that, to me, is like a brilliant art.

I remember Gavin asking me years ago if I wanted to do a performance at the end of a group show that he had organized. I told him I wanted to just introduce a celebrity into the room. I think at the time Gwyneth Paltrow was really hot. So I just wanted her to enter the crowd and for me to say, “Everybody, Gwyneth Paltrow!” And she wasn’t going to do anything, not even say hello. Well, he tried to help me for like weeks to find a big celebrity, and we couldn’t. Sadly, the project devolved. We found an agency where you could rent like a B-grade celebrity. I don’t even remember who I settled on, but it was not somebody who could electrify the room.

Rail: And that’s another form of cheating too, right? Celebrity used as a similar response as the cocaine thrill.

Pruitt: Well, you know, my father would tell his friends I was a con artist when they asked what type of artist I was.

Rail: Another way of dealing with what’s already there. How do these projects relate to the current works that are going to be in the show? They seem in some ways to be extensions from the “Suicide Paintings.” But how are you thinking about the landscapes in time that you’re selecting?

Pruitt: It’s a series of twelve clocks that run through the colors of the sky in the course of a day. The sequence starts at midnight and then ends up at midnight again, every two hours. They’re all set to the actual time.

Rail: It looks like the hands of the clock fade when it’s the exact time that they are painted as. In the case of your clocks, you actually lose the time when you’re in the moment of it, which is a poetic way of suggesting that the more you think about what time it is, the more you lose it.

Pruitt: You were really paying attention. The hands vanish in the moment that they mark, as if to announce visual perfection and clash with the sky when representing the past or anticipating the future.

Rail: It really is a brilliant conceptual piece. It’s made me think about how much time I spend thinking about time.

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Installation view: Rob Pruitt: Skyscapes, 303 Gallery, New York, 2026. Courtesy 303 Gallery.

Pruitt: Time is deeply personal.

Rail: Yeah, exactly. And how unaware of my body I become, how unaware of the present moment I become. But it really is that thinking about time itself makes you lose the exact moment, and you found a formal way to kind of illustrate that—among many things—and not to reduce it to one idea, because I think it’s more complex than that.

Pruitt: Well, they’re extensions of the “Suicide Paintings,” which are about freezing one’s own time. These are simply about mapping the time of day. As a practical matter, they make use of the painting skillset I developed making the “Suicide Paintings” to address a different way of thinking about time, as a cycle.

I don’t know that my philosophizing amounts to anything, but I certainly spend a lot of time doing it. I love thinking about how people like to use Facebook for sharing their friends’ and family’s birthdays and anniversaries, graduations, and things like that. And so, you know, I was really thinking about this framework that people have for celebrating time passing and commemorating time which has already passed. And so, in a way, the gradient skies that map out an entire month—or in the case of what’s going to be in the show, twenty-four-hour days—were a nice step back, like a reductive step back. It’s just really about time passing. But there’s one that is a picture of all twenty-four hours of the sky the day before this past presidential election that Trump won, one that I made the day of the presidential election, and then one the day after the presidential election. In all three of these paintings, the weather was basically the same. They look pretty similar, but in actuality they depict the pivotal moment that signals the decline of our democracy, even though the paintings don’t exactly show it until they’re anchored with these particular titles.

Rail: There’s the analogy of the lighthouse in George Kubler’s The Shape of Time, that if we see the lighthouse at night, we only know it by the light. But what about all the seconds in between? The actuality of time versus the events of it. And thinking about time and boredom, it’s Chantal Akerman being like, “What if I express an entire day of a woman’s life?” And then in that piece it’s the inverse. Momentous days sometimes don’t register in different modes of marking time. It seems existentialist, perhaps, but I can’t tell if it’s romantic or closer to Werner Herzog.

Pruitt: There’s room for all of it. I don’t disagree that it does seem like existential dread. But I do like thinking that, as we embrace the cliché of standing on the shore and watching the beautiful sunset, someone may be professing their love to whoever they’re with. Somebody elsewhere might be strangling someone at that same moment during that sunset. And someone else might be doing their laundry. And it’s all happening at the same time, which is really too big for me to grasp, and at the same time too boring to parse. But I can’t help but think that I’m compelled to deal with it.

Rail: There’s this beautiful Fra Angelico painting about the elders of the church, and it’s this huge scroll. I don’t know if you can recall it just now, but there’s like a funeral happening. There are people gardening. There are people getting lost on this mountain pass, and then there are monks who discover a dragon off in the corner. And it’s just overwhelming—the ordinary and the miraculous all happening in the same space. Hans Memling and Andrea Mantegna would do the same thing, hiding scenes within scenes to compress all of this multitude of time.

Pruitt: I can’t wait to look that up. You know, it’s exactly what I’m thinking about. Everything is happening all at once.

Rail: I do think a lot of your work is about navigating various forms of repression—not just the repression you experience, but the way we repress the sublime, or thinking of death, or all these different things. But I feel like the difficulty of taking on these subject matters is only possible because of your ability to distance yourself from it. Not emotionally—emotionally you stay very close. But then the work itself really delays that experience in the viewer.

Pruitt: Well, I love marking my time here on earth, and I love the cycles of it. I love living here in New York because we have four seasons. Apply, lather, rinse, repeat. I love having a dog because her routine mirrors mine: sleeping in the evening; alert in the morning; eating breakfast, lunch, and dinner; having poo-poo in the morning; having pee-pees at regular intervals throughout the day. I am so dependent on my rigid work schedule. The details that I’m interested in making art about only emerge through this repetition. I think it would be so much easier for me to explain what I do if I were an actual working comedian: I would simply tell you that I do it because nothing feels better than making people laugh, and I get off on it. Maybe it’s the same answer for me being an artist, but I’m afraid to say it because of what people will think.

I see life as seducing you to engage. Somebody that doesn’t engage deeply—that just sort of glides over the surface of everything—could have a very profound position and take on life. You don’t necessarily have to take a big bite out of the apple and savor it. Maybe we can reach the same high places just by skimming the surface.

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