Like the other trailblazing female gallerists of her era, Marian Goodman never set out to become a dealer. At university, she dreamed of joining the United Nations, but after she married and had two children, she followed another passion and enrolled in a graduate art history seminar at Columbia, where she was the only woman. Her first foray into the art world came around 1962, when she compiled a portfolio of cheap offset prints by New York painters to raise funds for her children’s school and met Franz Kline, who gave her drawings to sell. By 1965, she had opened a print gallery, Multiples, with several partners, paying her share with the funds raised from the sale of a Milton Avery painting given to her by her father, an accountant. She learned by doing: When the son of Jackson Pollock’s psychoanalyst asked Goodman to help him sell drawings that Pollock had used as payment for his sessions, she took them to a curator at the Museum of Modern Art, who bought them all. “The only thing that I forgot to do was ask for a commission,” she says, laughing, “and he wasn’t interested in being nice about it. That was my first week as a gallerist.”

Goodman, who turned 90 in June, sits in the living room of her homey duplex on New York’s Upper West Side, recalling the path she has forged to her current perch as one of the most venerated art dealers in the world. In those early days, she recalls, one prominent male dealer enthusiastically praised another for artist prints that Goodman had commissioned, and male collectors openly ignored her. Like her fellow female pioneers in the New York art world—Paula Cooper, Angela Westwater, Mary Boone, Janelle Reiring, Helene Winer, and Barbara Gladstone—Goodman emerged at a time when all of the galleries showing contemporary art could be visited in a single afternoon, American art reigned supreme, and making enough money to stay afloat was the goal. The art world then was a village, not the multibillion-dollar global industry it’s become.

Barbara Gladstone, in the living room of her Chelsea town house with Albee, one of her rescue dogs. The works here include (from top left): On Kawara’s August 8, 1975; Rosemarie Trockel’s O.T., 2006; and Lygia Clark’s Estruturas de Caixa de Fósforos (Matchbox Structures), 1964.

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

Art was also a field that lacked barriers to entry, unlike, say, the chauvinistic realms of finance or politics. “The art business curiously has had a lot of women in it, because it was considered harmless,” says Barbara Gladstone. “You could still be a good wife and mother. It wasn’t dangerous, because you weren’t going to make any money anyway.” Now 83, Gladstone, an art history professor turned prints collector and dealer, was interested in law growing up, but “very few of my friends had career ideas for themselves.” In 1980, she was twice divorced with three sons and living a well-to-do suburban life when, wanting to work with living artists, she opened a tiny gallery and began showing Jenny Holzer. Paula Cooper, 80, who this year is celebrating the 50th anniversary of her gallery, was separated from her second husband, with one child under 2 and six months pregnant when she opened her namesake gallery in 1968, in the then desolate factory zone that became SoHo. “I wouldn’t say it was brave, I would say it was nuts—I look back and think, Jesus!” Cooper recalls of her first downtown space. “Having to support two children forced me to become better at developing and supporting artists’ careers.”

Her opening show was an anti–Vietnam War benefit that included works by the Minimalists Donald Judd, Carl Andre, Dan Flavin, and Sol LeWitt—many of whom her gallery went on to represent. As conceptual art’s most ardent ally, the striking, soft-spoken Cooper has always followed her own taste. She was the first dealer to show Lynda Benglis, Joel Shapiro, and Elizabeth Murray, and the first to embrace multi-creative disciplines under one roof, hosting evenings of music, dance, and poetry, often with an activist bent. In 1974, when Artforum magazine was preparing a profile of Benglis, it refused to run the artist’s photograph of herself naked, holding a double-headed dildo between her legs. So Cooper ran the photo as a gallery ad in the magazine, knowing it would cause an outcry. (Benglis picked up the cost.) She also championed Andre, even while others questioned his 1988 acquittal in the death of his wife Ana Mendieta, who fell out of a window; his 2014 retrospective at Dia:Beacon was due in no small measure to Cooper’s efforts.

Janelle Reiring, with works by Metro Pictures artists, including (from left): Cindy Sherman’s Untitled, 2004, and Nina Beier’s vase and dog sculpture, China, 2016. “We were very careful about placing Cindy’s work with other art—no photography-only shows,” Reiring says of her and Winer’s efforts to shape the context for Sherman’s work. “We always made sure she was referred to as an artist, not a photographer.”

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

Though the details of their trajectories differ, all of these gallerists have steadily enlarged the renown and institutional presence of many of the artists now at the top of the art world. The Goodman roster alone boasts Gerhard Richter, Pierre Huyghe, and Julie Mehretu. “There was a joke that we used to make about Marian: ‘Carry a soft stick and lay it down hard,’ ” says the artist Lawrence Weiner of his dealer, who stands under five feet and speaks in a whisper. “She could handle anything. And there’s a kind of grandeur about her generosity.”

If none of them has built the global empire of some of their male peers, it’s because none aspired to what Janelle Reiring, 72, calls “very high-stakes art dealing,” in part because shaping artists’ careers, not making sales records, fueled their ambitions. “Our generation looks on it as a nurturing kind of profession,” she says. Yet, for all their contributions, clout, and staying power within the fiercely competitive art world, female gallerists have historically been under-recognized and overshadowed by their male counterparts. On ArtReview’s 2017 list of the 100 most powerful players in art, none of the dealers in the top 15 were American women—the highest ranked was Goodman, at 18. “In the beginning, I was surprised at the divide between men and women,” Goodman recalls. Asked if much has changed, she goes quiet. “That’s a hard one. Men are more impressed by men than by women, when it comes right down to it.”

Of course, other women had broken ground before them: Betty Parsons championed Abstract Expressionists like Jackson Pollock and Mark Rothko; Eleanor Ward gave Andy Warhol his first solo show, of his Pop paintings, including his “Marilyn” silk screens, in 1962. Through the 1970s and early ’80s, Leo Castelli and his ex-wife, Ileana Sonnabend, were the iconic dealers. The quietly forceful Sonnabend showed Jeff Koons, David Hockney, and Gilbert & George, while the gentlemanly Castelli represented such Pop masters as Jasper Johns and Robert Rauschenberg. Eventually, women like Goodman, Boone, and others became powerful tastemakers in their own right, exerting an enduring influence on global culture, and, by 1980, many other female gallerists had arrived in SoHo.

Angela Westwater, at home in her Fifth Avenue apartment with Malcolm Morley’s Fire Boat, 1999. The day this portrait was taken, Westwater had woken to news of Morley’s death. She has represented him since 1999, and this fall will open a Morley exhibition she was planning with the artist. The works in Westwater’s home run from Yves Klein’s La Victoire de Samothrace, 1962, to those by gallery artists Guillermo Kuitca, Susan Rothenberg, Tom Sachs, and Bruce Nauman, with whom she has worked since 1976.

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

One of the first was Angela Westwater, who is now 75. After immersing herself in the downtown art scene as an assistant at the John Weber Gallery and as managing editor of Artforum, she joined forces with the prominent European dealers Gian Enzo Sperone and Konrad Fischer, in 1975. Just as Sperone and Fischer promoted leading American artists from their own respective galleries in Italy and Germany, their joint gallery, Sperone Westwater Fischer, introduced avant-garde European artists to American collectors, as Goodman would also do. (Richter, for example, was represented by Westwater’s gallery before moving to Goodman.) Westwater’s other early shows included those by the American conceptual giant Bruce Nauman, whom she and Sperone continue to represent, and the Italian neo-Expressionists Enzo Cucchi and Sandro Chia. Around that time, Reiring, an English major turned gallery assistant, began showing art out of her loft while working at Castelli. “Collectors would come to Castelli”—among them, the British advertising magnate Charles Saatchi and the MoMA trustee Agnes Gund—“and I’d take them over to my apartment. I’d fire someone now if they did that while working for me.”

Helene Winer, in her aerie in TriBeCa, with a framed drawing by Martin Kippenberger. “He was particularly crazy and intense,” Winer says of Kippenberger, whom Metro Pictures began to show in the mid-1980s. “I was struck by his free-roaming mind. He did everything then—not just painting—though now he’s primarily remembered as a painter.”

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

In 1980, she teamed up with Helene Winer, a former director of Artists Space and curator at Pomona College Museum of Art, in California, whom she’d known since high school in Los Angeles, to open Metro Pictures, launching the careers of Cindy Sherman, Robert Longo, Louise Lawler, Richard Prince, and other artists who were using photography as a way to comment on the media-saturated environment. Lawler had been the “slide girl” at Castelli (at a time well before JPGs); Sherman, the receptionist at Artists Space, who occasionally showed up to work dressed as a nurse or ’50s-era secretary. Winer, who had hired Sherman, recalls seeing the early stages of her landmark “Untitled Film Stills.” A number of the single-image dramas, in which Sherman transformed herself into a variety of female archetypes, were shown at Artists Space in 1978. “They were just so good that you didn’t miss the point,” Winer, 72, says. “There were other women at that time taking photographs of themselves doing things. But this wasn’t the same at all, because Cindy’s pictures weren’t about her. She was way ahead of what these other conceptual women artists were doing.” The ties forged then have endured to this day, says Sherman. “I would have been intimidated going to an established gallery like Castelli. I think our bond developed because we were all new to the game, so there was this kind of fresh, innocent way of taking it on.” Sherman and Richard Prince became a couple after Metro Pictures opened, “and that was just a disaster,” recalls Reiring, “because her career took off right away and we’d have to call them all the time. There were no cell phones then, so Richard would answer and we only wanted to talk to Cindy. He did not accept her success at all and wasn’t nice about it. Couples at the gallery was not a good thing.”

The ’80s brought new money, new collectors, and the erosion of the idea of collecting as the private preserve of the few. Collectors of new art could name-check the artists on their walls with swagger, and contemporary art was suddenly viewed as a hot commodity—and an investment. Young artists and even dealers became celebrities. With her glamour, smarts, and audacity, Mary Boone, 66, was the first gallerist to become known outside of art circles after New York magazine dubbed her “The New Queen of the Art Scene” in a 1982 cover story. The daughter of Egyptian immigrants to Erie, Pennsylvania, Boone had grown up on welfare after her father died when she was 3. She and her two sisters moved with their mother to Pasadena to live with relatives. At 19, she had just finished studies at Rhode Island School of Design when Benglis, whom she had met at a lecture, urged her to relocate to New York and later got her a job as secretary to her then boyfriend, the gallerist and art historian Klaus Kertess. At his uptown Bykert Gallery, Boone worked with Brice Marden and Chuck Close before opening her own gallery in 1977, in a tiny space on the ground floor at 420 West Broadway, the now storied building that was also home to the Castelli and Sonnabend galleries. It was a canny move: The freight elevator always broke down on Saturdays due to the overflow crowds, she recalls, and she figured she’d draw the impatient visitors waiting to go upstairs. Her debut show included paintings by David Salle, Ross Bleckner, Warhol, and Julian Schnabel—only the Schnabel sold. Schnabel was a cook at the Lower Manhattan Ocean Club restaurant when Boone met him and was left “bowled over” by his work.

Mary Boone, in the Upper East Side apartment she bought in 1985 with her ex-husband, Michael Werner, in part with the funds generated by selling Andy Warhol’s Pink Disaster, 1963, which she had purchased from the artist Cy Twombly for $25,000 in 1980. She stands next to Barbara Kruger’s Untitled (Go/Stay), 2006–2007, in her bedroom (which also houses an Empire giltwood bed). Elsewhere, the home’s walls are hung with works by Julian Schnabel, Sherrie Levine, and more by Kruger.

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

“Julian and I were the same age and two hot-headed, ambitious, explosive personalities­—and young and immature,” she says. In 1981, the buzz of the New York art world centered on the double show that Boone had organized for Schnabel simultaneously at Castelli and her own gallery, which not only gave ­Schnabel the imprimatur of Castelli but gave Castelli a line to new money and painters. “Leo sanctioning this new generation made it good for everybody,” she recalls. Soon Boone was showing the rising stars Jean-Michel Basquiat, Francesco Clemente, Barbara Kruger, and, with her then husband, the powerful if reticent German dealer Michael Werner, Sigmar Polke and Georg Baselitz, among others. She recalls crying at her desk after Schnabel left her gallery for Pace. By then, she’d taken on Basquiat, who was already a phenom in the art world, though Boone says she was wary of the hype (“and that’s the word used about me!”) and wanted him to slow down. “And Jean-Michel comes up behind me and puts his arm around me and says, ‘Don’t worry, Mary, I’m going to be a much greater artist than Julian would ever be for you.’ I always think of that.” His own opening at Boone made good on that promise, with Warhol in attendance and collectors lining up. Looking back, Boone says she wishes she’d done more “to get Jean-Michel sober.” (Boone herself got sober in 1998, part of a personal reset in the wake of market downturns and the end of her marriage to Werner—though not of their business relationship.) “Andy was the only person Jean-Michel would listen to about going to rehab. And then Andy died.”

While Boone is often portrayed as the symbol of the flashy, moneyed ’80s (how quaint they seem now), for some, she ushered in a new freedom. “Mary gave herself permission to do everything that had been taboo before,” says Gladstone, “like to wear Chanel suits and have a driver. Suddenly, there were stories about where she ate dinner. She became a huge personality, and public about herself in a way that I don’t think any other woman before her ever was. She expected to make money and be successful. Now nobody thinks anything of it. She gave a whole bunch of women permission to just be yourself, do whatever you want.” Boone also had a marketing sense, “which no one else had even thought of,” adds Gladstone. “Marketing? You just did what you did, and people came and they liked it or they didn’t. I don’t think you’d have Larry Gagosian in the same way without having had Mary. Because she made herself a brand before he did. She made the art world sexy.”

Paula Cooper, in her penthouse apartment in Chelsea that’s filled with works by gallery artists and friends. From left: Donald Judd’s Untitled, 1967, and Jan J. Schoonhoven’s R 70-19, 1970. Other rooms hold a Sol LeWitt wall drawing and On Kawara’s telegrams to Cooper from his “I Am Still Alive” series, 1969–2000.

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera.

Gladstone, Boone, and the others have continued to flourish over the years, navigating recessions, the advent of art fairs, globalization, and fallow periods in artists’ careers—and in their own. The center of gravity has shifted from SoHo to Chelsea, and artists have left them for other galleries, while new ones have come in. “Artists peak at different times,” Gladstone says. “You have to sense in someone’s work the possibility of longevity.” She recalls adding Matthew Barney to her roster after seeing his first elaborate sculptural installations, combining performance and video, in his studio. “I had never seen sports and science connected to visual art and sculpture in the same way,” she says of the gender-bending, body-focused work. “It was mind-boggling.”

In his first solo show, in 1991, Barney filmed himself climbing naked across the Gladstone Gallery’s ceiling and down a stairwell into a huge walk-in refrigerator. She now shows stars ranging from Shirin Neshat and Sarah Lucas to the digital wunderkind Ian Cheng, and represents the estate of her old friend Robert Mapplethorpe, whose 1984 photograph of Paula Cooper was the basis for Rudolf Stingel’s monumental painting of her—the lone work in his 2005 show at Cooper’s gallery. Boone, meanwhile, has brought on the curator Piper Marshall to showcase young female artists, alongside stalwarts like Barbara Kruger and Ai Weiwei. At Cooper’s Chelsea gallery, lines stretched around the block for The Clock, Christian Marclay’s 24-hour paean to cinematic history, which was screened 24/7 over several weekends in 2011. When I ask Cooper how she wooed recent recruits Tauba Auerbach and the painter Cecily Brown, she corrects me. “I’ve never stolen anyone,” she says, recalling that after Judd left Castelli for her gallery, Castelli marched over to her office and demanded to know, “ ‘How much did you offer him?’ Judd, at that point, wasn’t selling, and Leo didn’t understand his work, really, and wasn’t paying attention to him. Once I denied offering Don anything, Leo invited me to lunch to explain that Don was unhappy because Leo was spending too much time on his romantic affairs. I really got such a kick out of that.”

Marian Goodman, in the dining room of her Upper West Side duplex overlooking Central Park. On each of the room’s walls is a work by the gallery artist Gerhard Richter. Shown here is his Kerze, 1982, which Goodman purchased for $5,000 at the time. Her eye for art was honed, in part, by her father, who arranged images of artworks he liked in the family living room when she was growing up.

Photograph by Sharon Lockhart; Styled by Felicia Garcia-Rivera. Sittings Editor: Sam Walker (Reiring, Goodman); Hair and Makeup by Ellin Guhin at See Management (Westwater, Gladstone); Hair By Mia Santiago at See Management (Reiring, Goodman); Makeup by Cassandra Garcia At See Management (Winer, Reiring, Goodman); Gladstone wears the row dress and shoes, her own jewelry; Photography Assistant: Alex Slade; Fashion Assistant: Gabriela Harrigan; Production Assistants: Christina Montes, Luke Smithers.

The amount of money now swilling around the auction houses has distorted values in every sense of the word, say these gallerists, and artists’ demands have risen as they have taken charge of their careers. But now, largely because of their groundbreaking work, women dealers are hardly an anomaly. None of those featured in this portfolio has any plans to retire—or much desire to contemplate the future of her gallery when she is no longer at the helm. In the end, says Gladstone, “it’s up to the artists.” For Boone, the relationship between artist and dealer is unique. “The ­gallerist creates the segue between the artist’s studio and the public. You give a voice to the artist and make the work open to the world.” Goodman says that “I’ve told my son and daughter that I’d love to see the gallery continue. But I have no control over what happens.” Cooper echoes that sentiment. “Whoever is running it will do whatever they do. I’m gone.”