One day in the summer of 1982, the art dealers Penny Pilkington and Wendy Olsoff were driving through the English countryside when their car broke down. The two had met the previous year as entry-level employees at Theo Waddington Gallery on the Upper East Side of Manhattan. Though their day jobs were uptown, and they lived in a two-bedroom railroad apartment three blocks away, splitting the rent of $750, the pair shared a disinterest in the art they saw there — Waddington showed Fauvists and Inuit artists, while his neighbors were mainly gentlemanly dealers of old masters, Impressionists and male abstract painters. Pilkington and Olsoff were young, in their mid-20s, but they were also gutsy, no-nonsense and imaginative, and they began to fantasize about opening their own space together. They had traveled to the U.K., in part, to visit Pilkington’s parents, who ran London’s Piccadilly Gallery, which focused on turn-of-the-20th-century European art. But that summer day, as would happen both literally and figuratively at various points in their working relationship, they found themselves stranded at the side of the road. After looking under the car’s hood, Olsoff recalls, Pilkington removed her stockings, as if this were a very normal thing to do, and tied them in place to create a makeshift replacement for the blown-out fan belt. “It worked for just long enough to get to the next garage,” Pilkington recalls. For Olsoff, it was a sign that they would always be able to get by.

They founded the gallery PPOW, named for their initials, the following year. Ever since, the pair have displayed a knack for being about a decade ahead of the market in terms of taste, showing socially engaged work that reflects their deeply held belief in content over money. Though their gallery’s inception coincided with the apex of the art world’s commerciality up until that point — in 1983, the New York market alone was estimated to be valued at $2 billion, an unprecedented high — the partners remained true to their interests and ideals not only during that first decade, when dealing art became a viable path to achieving substantial wealth and power, but also throughout the intervening years, refusing to buy into the larger trends and waves of hype that tend to drive the industry. Historically, going against these prevailing currents has not been a recipe for success in the art market, but PPOW has nevertheless stayed in business when many of its former peers have not. It’s done so partly in spite of its program — during the culture wars of the late ’80s and early ’90s, for example, it represented queer artists and artists of color whose work was not merely undervalued but whose very existence was seen by certain conservative groups as a fundamental threat to American values — and also because of it. Though PPOW has moved from the East Village to SoHo to Chelsea and, this year, to TriBeCa, its reputation for integrity and commitment to uplifting work made on the margins have remained constant, cementing its place as the quintessential downtown art gallery, and it is perhaps the last gallery that continues to embody that spirit so fully: It is both a custodian of defining chapters in the city’s cultural history and a reliable indicator of its future.

Running a gallery is not an easy business, and most do not last long. They live and die on the changing tastes of collectors, and many struggle just to meet their overhead. The art business is at best a labor of love and at worst a symbol of late capitalism at its most ridiculous. But PPOW’s adaptability and track record of fostering the careers of artists who have since become legendary is nothing short of remarkable.

In the mid- and late 1980s, the gallery exhibited pioneering East Village artists including, most notably, David Wojnarowicz, a former teen runaway who had fled an abusive upbringing in suburban New Jersey and who had, for a period, lived on the streets of Manhattan. By the time Olsoff and Pilkington presented his 1989 solo show “In The Shadow of Forward Motion” — bringing together roughly 35 of his explicitly queer pieces across the mediums of photography, painting and sculpture, each illuminating his lasting preoccupations with, as he once put it, “this killing machine called America” — the artist had already established himself as a vital source of dissent and passionate creativity during a period of increasing social conservatism and continued silence in the face of the AIDS crisis.

In 1990, PPOW achieved another landmark by debuting the photographer Carrie Mae Weems’s “Kitchen Table” series. Pilkington and Olsoff had included images from the Oregon-born artist’s vibrantly tinted portraits of Black children in a 1989 group show and, soon after, drove to visit her at Hampshire College, where she was teaching. There, seated in her studio, Weems mentioned a new body of work she was excited about and produced, from under her desk, the intimate black-and-white photographs that make up “The Kitchen Table Series”: carefully staged vignettes, in which Weems plays the matriarch of a fictional family, that would initiate a new conversation in the art world about the lived experiences of Black women and help establish Weems as one of America’s greatest living photographers.

Also in 1990, Pilkington and Olsoff began representing the visionary New York-based Chinese-American painter Martin Wong, whose detailed, diaristic canvases — each a snapshot of the ruin and resilience he observed daily across the rapidly changing city — similarly shed light on lives that had been pushed to the margins. (Since his death from AIDS-related illness in 1999, the gallery has represented his estate.) And a decade later, in 2002, the partners started working with the American multimedia artist Carolee Schneemann, known for her boundary-pushing works about sexuality and gender — including the now-canonical 1975 performance piece “Interior Scroll,” during which she pulled a scroll from her vagina and read aloud from it to a live audience. (Since her death in 2019, they have represented her estate, as well.)

Today, Pilkington and Olsoff, both 64, aren’t unique in working with artists from communities that have historically been underrepresented in the art world — in recent years, demand for pieces by long-ignored groups has grown, and gallery owners themselves have become more diverse — but they are unusual among gallerists both in their longstanding commitment to what Olsoff describes as artists with “something to say about our social environment, and the voices that weren’t seen,” and also in their resolutely straightforward, transparent approach in an industry not known for its ethics. “There are realities in being a gallery and sustaining it,” says Brian Donnelly, the artist known as KAWS, who has been a collector of PPOW’s artists, especially Wong, since the 2000s. “And they walk the line between getting it done and staying open and still being very human. That’s rare in this space.”

In the 38 years since they opened, the partners have arguably also helped create a market for artists whose work was previously hard to move. As the influential feminist artist Betty Tompkins, who recalls being turned away by countless galleries throughout the ’60s and ’70s, and who was unrepresented in New York for over five years before joining PPOW in 2016, says, “Part of their job is to make whatever you’re doing popular, even though it didn’t start out that way.” Pilkington and Olsoff’s shows of work by Wong, Wojnarowicz and Schneemann have persistently underscored the importance of their oeuvres and helped secure major museum retrospectives (for Wong at the Bronx Museum in 2015; for Schneemann at MoMA PS1 in 2017, two years before her death; and for Wojnarowicz at the Whitney in 2018). They’ve also used that attention to uplift younger artists, for example by showing a selection of the Colombian-born Carlos Motta’s photographic self-portraits and video works alongside images by Wojnarowicz that explore similar themes of queerness and death, as they did in 2019 at the ARCO fair in Madrid, or by highlighting the affinities between the practices of Wong and the Brooklyn-based painter Aaron Gilbert, as in the recent show “1981-2021.” That exhibition, which juxtaposed social realist canvases made during pandemics 40 years apart — Wong’s depicting the displaced communities of the Lower East Side during the AIDS crisis and Gilbert’s showing the enduring precariousness experienced by New Yorkers today, especially after the arrival of Covid-19 — was in some ways a reflection on the gallery’s own history, too, and a reminder that PPOW has continually shown work that responds to the present moment, not for commercial reasons but because that’s what it’s always done, and especially when the subject matter has been difficult. “I feel like they’re ready for an artist to be addressing conversations in a way that’s different or unexpected, and really brings nuance to them,” says Gilbert. “Whereas a gallery that’s jumping on a bandwagon, they’re just going to want something that already makes sense to them.”

And if PPOW hasn’t opened an outpost in Hong Kong or Silicon Valley, or launched a publishing imprint or a podcast, as some larger New York galleries have done over the past decade, it’s not because it doesn’t have the ability to but because Pilkington and Olsoff have never equated success with building an empire, which has become the default goal for many of the pair’s contemporaries. “Our dream,” says Olsoff, “was not to be anything more than a young gallery in the East Village.”

IN MAY 1983, Julian Schnabel’s painting “Notre Dame” (1979), from his series of mosaiclike canvases encrusted with the shards of shattered dinner plates, sold for a then-unheard-of price of over $90,000 at Sotheby’s. His gallerist at the time, Mary Boone, was one of a cohort of canny dealers that also included Larry Gagosian and Tony Shafrazi who had introduced Wall Street money to the art market. Based in SoHo — which by then had transitioned from a slightly dangerous district of abandoned former factories inhabited by artists, as it had been in the late ’60s and ’70s, into a high-end shopping enclave — these gallerists knew how to aggressively generate buzz and drive up prices in a manner that felt familiar and appealing to the finance world. By contrast, the East Village, which also had a reputation as an artist’s haven in the ’60s and ’70s, still had a scrappy feel and comparatively cheap rents in the early ’80s, even as a new wave of avant-garde galleries, many founded in reaction to the gaudiness of SoHo, began to open in its beaten-up tenement buildings.

It was also in 1983 that Olsoff and Pilkington found a storefront on East 10th Street whose landlord was willing to rent them an apartment on the building’s sixth floor, as well. The apartment had black ceilings and strangely thick vinyl floors, but the combined rent for both spaces was $1,000, so they signed the lease. Then they set about finding artists and an agenda. “We knew what we didn’t want,” says Olsoff. “The work being shown then was a lot of men — Schnabel, and the Italians, like Francesco Clemente. They’re not bad artists, but it just did not resonate with us.” In the East Village, meanwhile, young galleries and artist-run venues such as FUN, Civilian Warfare, Gracie Mansion and Nature Morte were directly responding to what was happening in the city. “There was a raging ethos, like now, just needing to come out,” says Olsoff. A friend tipped her and Pilkington off about a show of work by the British artist Sue Coe — who made political illustrations for The New York Times and Raw, Art Spiegelman and Françoise Mouly’s alternative comics magazine — that was happening on Staten Island. They went and fell in love with Coe’s angry, explicit graphite and gouache depictions of social injustice, and soon after put on their first exhibition: a selection of the illustrator’s works, rendered mostly in black, white and gray, and covering topics including racism, sexism, exploitative housing practices and health care inequality. The largest painting in the show, “Woman Walks Into Bar — Is Raped by Four Men on the Pool Table — While 20 Watch” (1983), which is now part of MoMA’s permanent collection, is a detailed nearly 8-by-10-foot rendering of an atrocity reported in 1983 that is at once devastating to look at and beautifully executed, with echoes of old master crucifixion scenes. “It was a very pointed show,” says Olsoff. “We were scared we’d get rocks through the window. But collectors bought it.” The exhibition sold out, earned the gallery a review in Artforum and set the tone for the program PPOW would stick to for the next four decades. “There’s always been this thread of political figurative work,” says Olsoff. “There have been so many stories and so many types of work, but it still retains its relevance.”

The East Village at the time, recalls Olsoff, was in some ways “like a much more diverse, dysfunctional college campus.” She and Pilkington would go to openings every evening after closing up, and later run into artist and gallerist friends at venues like the Pyramid Club on Avenue A. “It was a very strong community,” says Pilkington. But it was also the beginning of the Reagan era, and “the social conditions were getting bad,” says Coe. The neighborhood’s streets were piled with uncollected trash. Gentrification, which the influx of galleries had accelerated, was leading to forced evictions. And there were surreal encounters between longtime residents and new arrivals. A drug dealer who worked on the same block as Olsoff and Pilkington once offered them several bottles of champagne ahead of an opening. Still, the galleries provided space for the growing resistance to the larger inequalities the neighborhood embodied to find expression. “Artists reflect what’s going on, they absorb everything by osmosis, but that was being crushed by Abstract Expressionism, which was still from the 1950s,” says Coe of the New York art world in the early ’80s. “PPOW was one of the first galleries to open up a narrative arc. The artists they chose were telling stories of what was going on, and people could walk into this little storefront gallery and see their own stories in the art.”

Pilkington and Olsoff moved to a larger space on East Eighth Street in 1986. By then, Olsoff recalls, money was really coming into the neighborhood: “Sunday was a big day, and people arrived in cars to buy art. Everyone was feasting but hating on the East Village, too.” The partners asked Pilkington’s friend the British architect John Pawson, who was then just starting out, to renovate their new gallery. True to the style he would later define for himself, and less improvised than their first outpost, it had poured concrete floors, white walls, imposing minimalist columns and a dramatic flight of stairs that visitors descended to get into the space. The gallerists also expanded their roster and began to establish a stable of loyal collectors including Steven Johnson and Walter Sudol, a couple who remain major supporters of PPOW and today run the Second Ward Foundation arts nonprofit in Hudson, N.Y.

Then, in August 1988, the East Village gallery scene effectively came to an end with the Tompkins Square Park riot. The tensions that had been building in the neighborhood finally reached a head with a demonstration against gentrification — protest banners read, “Die yuppie scum” — at the park’s East Eighth Street entrance that escalated into a clash with the police, whose violence was so extreme it prompted a string of further protests. The area became a no-go zone for months. “But we were very lucky in that, for some reason, we realized that the East Village was shifting,” says Pilkington. The partners’ sensitivity to the city’s changing cultural tides meant that, once again, they were ahead of the curve. They had moved to a space on Broadway just a few weeks before.

THOUGH THEY HAD BEEN reluctant to decamp to SoHo, which they felt was more commercial, Olsoff and Pilkington stayed on the third floor (they couldn’t afford the first) of 532 Broadway for a decade before moving a few blocks southwest to 476 Broome Street (where they were also on the third floor) in 1997. During its SoHo years, PPOW put on important exhibitions that, according to Olsoff, very few people actually saw. The tone of the art world shifted dramatically during the ’90s. While the decade heralded an increased interest in identity politics in art and continued challenges to the industry’s white- and male-dominated status quo, those impulses were matched by a creeping sense of apathy, brought on by the rise of globalization and neoliberalism — or the fantasy that, perhaps, we had found the solution to our problems in a deregulated market. Despite the economic recession that had begun in 1987, a handful of living artists like Jeff Koons, who had in fact come up in the East Village, were now regularly selling works for seven-figure sums, and the arrival of the internet helped circulate these figures and propel their recipients to celebrity status.

“Everyone was running to Chelsea to see Koons and Claes Oldenburg, and we thought, ‘What are we doing? We have so much better work here,’” recalls Olsoff. In SoHo, the partners honed their list of marquee artists, showing Wojnarowicz, Weems, Wong and the American painter Nancy Spero. It was there, in 1992, that they put on Wong’s influential exhibition “Chinatown USA,” whose images lovingly chronicled the Chinatowns of New York and San Francisco. “They were some of our best shows, with works that are now terribly hard to get by artists who are now really famous,” says Olsoff. But while Weems’s photographs sold well, the popularity of new digital mediums had flattened the demand for painting. Wojnarowicz and Wong, who both died in the ’90s, were important precursors to the decade’s identity-focused work, but the social struggles they had been so intimately involved with had either shifted or found more fashionable champions. Pilkington would periodically beg the gallery’s landlord for more time to make rent. And for stretches of time, she and Olsoff, who then had two children with her now ex-husband, stopped paying themselves salaries. “It was very stressful,” says Olsoff. “And it was a whole decade.” They recall scraping together the funds for a booth at the Art Basel fair in Switzerland, and the despair of not selling work there while sinking money into accommodations and overpriced food, only to return to New York in June, before the slowest time of the year, with no potential sales on the horizon until September.

“We have had many, many sleepless nights. Very many,” says Olsoff. “Friends and artists died of AIDS. There was the dot-com crisis. There was the World Trade Center, when we were right there on Broome Street. I mean, it was really horrible.” And while they like to joke that they are simply too proud to quit, she and Pilkington have made it through, in large part, because of each other and the strength of their working relationship. “I had shown with some partners before, and it was always bad,” says Betty Tompkins. “They had never had ‘the talk.’ It’s like getting married: “What are you responsible for? What am I responsible for?” But I was really impressed with how Wendy and Penny divvy up the duties.” Olsoff, who is more gregarious, tends to handle outward-facing tasks and now does the majority of the gallery’s studio visits, while Pilkington, who is unflappable and as a child would take apart and reassemble a broken vacuum cleaner for fun, solves problems and creates stability. In conversation, they often finish each other’s sentences, and their skill sets are complementary in even the smallest of ways: When we meet for our first interview at a cafe in March, it is Pilkington who reaches for the check at the end of the afternoon, while Olsoff — who says, with a laugh, that she can’t do basic math — continues to chat animatedly. “They’re very chalk and cheese,” says Pawson. Or, as Coe sees it, “one is the live wire and one is the grounding, so if you get the wires mixed up, the building could burn down.”

In 2002, PPOW made another reluctant move, this time to Chelsea, where, in 2009, the gallery was, in fact, damaged by a fire. It began at night in the loft above, which was being renovated, and eventually burned through the gallery’s ceiling. Pilkington and Olsoff had, by that point, spent two decades in an uneasy game of cat and mouse with gentrification — arriving in a neighborhood that was just starting to experience it, only to be forced into the next one by its effects — and this particular catastrophe seemed like the culmination: The art world’s incursion into Chelsea had helped transform the former industrial zone into a desirable area for condos, and one of them almost razed the gallery. “Grab the Schneemanns, grab the Wongs, just grab them,” Olsoff remembers yelling. They were also able to salvage some of the works by the Dutch artist Teun Hocks, which they had been installing at the time, and somewhat miraculously, they still managed to open the show on time, in an alternate venue. But it was another chapter of another difficult decade. “It was tunnel vision after that,” says Pilkington. “Wendy concentrated on the shows and the program, and I concentrated on the insurance claim. I don’t even know what else happened during that time. All I know is, I got the money.” Still, that same year, they mounted an exhibition of Schneeman’s long-overlooked paintings that eventually led to her large traveling retrospective in 2017, and during their time in Chelsea they began working with several of the artists — including Motta and Tompkins, as well as the Brooklyn-based painter Robin F. Williams, the American feminist performance artist Martha Wilson and the young California-born painter Jay Lynn Gomez — who would define their program in the years to come. “A lot of curators came to that space,” says Olsoff. “It’s like you plant seeds whenever you do these shows. Nowadays, people are blinded: They think everything has to happen now. But I have a thing I like to say, which is, ‘Yeah, this show didn’t sell — which means it’s a really good show.’”

OVER THE PAST two decades, Pilkington and Olsoff have continued to tighten their roster, focusing on their strengths. They now have a staff of 11, which includes Olsoff’s daughter, Eden Deering, and, at least outside the worst months of the pandemic, they no longer live in fear of having to forgo their own paychecks. “We just kind of grew into ourselves,” says Olsoff. “But it took a while.” For the first time since leaving the East Village, they are also operating on the ground floor again. In January, having decided that Chelsea had become too corporate, they moved the gallery into an 8,000-square-foot space on Broadway, below Walker Street, that was formerly occupied by the cowboy boot store Western Spirit. The neighboring blocks are still lined with shops selling sneakers and Timberlands and, once again, the other galleries in PPOW’s vicinity seem to share a sensibility. Just behind it, on Cortlandt Alley, is Artists Space, another legendary venue where PPOW was featured in a 1984 group show called “New Galleries of the Lower East Side.” “It’s sort of like a homecoming,” says Olsoff, “because I feel the mood is similar.”

Still, she worries about what the current direction of the art world will mean for the future. Last year, when fairs and foot traffic were limited to prevent the spread of Covid-19, the industry adapted in ways that provided some glimmers of hope — many galleries, for example, hosted virtual events and online exhibitions that dramatically lessened carbon footprints — but mostly, the art world’s responses seemed indicative of its fickleness and propensity for creating prospecting frenzies (take the emergence of NFTs). The pandemic also exposed the financial precarity inherent in running a modestly sized gallery, and some, like Venus Over Manhattan, were forced into lawsuits concerning rent, while others, like the pioneering Metro Pictures, which has represented artists including Cindy Sherman and Robert Longo, are set to close by the end of the year. In the current climate, is staying small no longer a successful survival strategy but an existential threat? Whereas Olsoff and Pilkington’s role models — New York gallerists like Paula Cooper, Marian Goodman and Barbara Gladstone, who established themselves in the years before they did — each eventually opened outposts in other states and abroad in order to compete with their larger neighbors in Chelsea, PPOW has so far remained committed to staying local. And as a certain handful of galleries continue to grow, casting larger and larger shadows over their peers, that position might be harder to hold. (“We could support it,” says Olsoff of expanding overseas, “and I wouldn’t rule it out.”)

She is concerned, too, about who the dealers of her daughter’s generation will look up to, and how they will define success. To this end, the partners act as unofficial advisers to a loose network of younger gallerists, fielding phone calls about unusual sales and best practices. They speak regularly, for instance, with Fabiola Alondra and Jane Harmon, a pair of friends who founded the gallery Fortnight Institute five years ago, just a few blocks from PPOW’s first space. “They’re nurturing other talent,” says Harmon, “which is not a common thing.” And in conversation, Olsoff and Pilkington return again and again to the importance of having created a team that embodies their vision and values, and that will be able to continue upholding the legacies of their artists in decades to come. It is those legacies, in particular the estates of Wong, Wojnarowicz and Schneemann, that keep the pair up at night now. “And they should,” says Olsoff. At times, it has felt like a crushingly heavy responsibility. “We’ve been holding up these artists for 10, 20 years,” she continues. “But you know that this group of artists or this writer or this community lives and dies by them, which gives you just enough that you keep doing it even though you’re not making any money. And then, somehow, it seeps out into the world.”

On a rainy night in March, almost a year to the day after New York entered lockdown, I made my way to PPOW to see, for the second time, a show by the artist Guadalupe Maravilla. Fleeing the civil war in his native El Salvador, Maravilla immigrated to the States in the 1980s at age 8 and didn’t receive citizenship until he was 27. In 2013, he was diagnosed with colon cancer and, while undergoing radiotherapy, began to explore sound as a tool for healing. After he recovered, he wanted to share the techniques he’d learned, and in 2017 he started hosting sound baths for members of New York’s undocumented community, in an attempt to alleviate the collective trauma of their experience — a practice he continued during the pandemic, in addition to raising funds for and distributing meals to those in need. As part of his first solo show at PPOW, he presented six towering, ornate sculptures, which he refers to as “Disease Throwers,” made from materials gathered from across Central America and including pieces of anatomical models, plastic children’s toys, loofahs, birds’ talons and instruments. At the center of each shrinelike assemblage is a functioning gong and, on several evenings during the course of the exhibition, he played them after hours for whichever ten people had signed up to attend, as I had that night. Lying on a concrete floor surrounded by strangers, while I was technically working but also trying to relax, didn’t seem like the ideal conditions for a meaningful encounter. But the sounds were transcendent, like the eerie ringing you might imagine planets make as they move around their orbits, and I remembered how it felt to be immersed in something larger than my own newly constrained existence. While some contemporary art galleries can make visitors feel as if they are simply customers in a store they can’t afford, Maravilla’s sound baths, in a way that is entirely typical of PPOW’s approach, made the simple white-walled space into something greater: a venue for a communal, transformative experience at a time when people needed it most.