In 1952, as was pouring his energy into paintings of fiendishly faced women, painted a seated portrait of her husband with barely any face at all—no mouth or eyes, just an oval smudge with a mop of gray hair and a black mark in place of his strong brow and nose. As tempting as it might be to read Elaine’s erasure of Willem’s face as marital sparring by paintbrush, the image was far from the only faceless man she painted.

Over the course of her 40-year career, de Kooning painted a wide range of subjects—from bulls and basketball players to cave paintings and Bacchus statues—but portraiture was her passion, and men were her longest-running fascination. Indeed, she painted dozens of them, stripping them of distinguishing features in a way that updated the traditional genre of portraiture with the language of modernism.

De Kooning—born Elaine Fried in Sheepshead Bay, Brooklyn, in 1918—not only infiltrated the male-dominated scene of downtown New York in the 1940s and ’50s, she was also one of its social anchors—not least because she was sharp as a tack and a witty conversationalist, and, as legend has it, could drink many of her companions under the table. Reviewing one of her exhibitions in 1963, New York Times art critic John Canaday—who never warmed up to abstraction, let alone de Kooning’s work—portrayed her contribution to in only mildly patronizing terms, describing her as combining “the functions of mascot, sybil, and recording secretary of the movement.”

De Kooning was indeed an eloquent and ambitious writer with an eye for innovative work and familiarity with the fresh crop of artists the city was attracting, and ARTnews, the critical art publication of the era, hired her as a reviewer in 1948. There, de Kooning widened her social circle and built upon her reputation as an outspoken, independent thinker. Today, her legacy resides in those writings as much as in her art. “It was a really important part—maybe the most important part,” said her biographer, Cathy Curtis, the author of the 2017 book A Generous Vision: The Creative Life of Elaine de Kooning.

Yet de Kooning also worked to carve out a niche for herself as an artist among New York’s avant garde, and painting portraits was one way to accomplish that. “[Willem] just always thought that the portraits were pictures that girls made, so I made portraits,” she told Lee Hall, one of her biographers. “I had that area free; I had to do it myself; I didn’t have to make decisions. I knew I was going to make a portrait and it didn’t much matter of whom; once you are set to make a portrait, you’re free to make a painting.”

But painting men (and a few women) was also a pleasure—a way for the artist to become intimately acquainted with her subjects. “Her portraits were done out of passion, especially when it came to men. She loved men. You see the greater spontaneity and certainty and a much stronger sense of gesture in her paintings of men,” says Jim Levis, who represents her estate. De Kooning had no shortage of male friends (or lovers), and many were as culturally relevant as Willem, or Bill, as he was known, who she married in 1943. Artist , poet , dealer Leo Castelli, critic Harold Rosenberg, artist , and poet are among the men de Kooning brought to life in full-length or seated portraits, distilling each sitter’s character while energizing the canvas with the bold colors and rapid brush strokes typical of the . Those portraits now serve as a visual archive of a major moment in New York’s history not only because of who they show, but because of the Abstract Expressionist style in which they’re painted.

Like her more abstract-leaning compatriots, de Kooning was trying to get at something visceral beneath the surface. She was interested in capturing the nuances of body language, and by blurring facial features, she could shift attention away from the eyes and toward the body. A portrait of her close friend, New York School poet Frank O’Hara, is one such example. “First I painted the whole structure of his face,” de Kooning once explained of the work, “then I wiped out the face, and when the face was gone, it was more Frank than when the face was there.”

“She wanted to capture the pose of the whole person, the way you’d see someone from a distance and know who they were,” says Brandon Fortune, chief curator of the National Portrait Gallery in Washington, D.C., and organizer of the 2015 exhibition “Elaine de Kooning: Portraits,” one of the rare museum exhibitions over the years to focus on the artist’s work. And while “she liked to think of herself as a painter first, not as a woman painter,” says Fortune, de Kooning was certainly wise to the implications of turning the tables on the male gaze. In her essay for the National Portrait Gallery’s exhibition catalog, Fortune quotes the artist’s comment to an interviewer in 1987: “[In the past] women painted women: , , and so forth. And I thought, men always painted the opposite sex, and I wanted to paint men as sex objects.”

That intention comes through most clearly in her 1954 portrait of fellow artist and writer , who sits in a chair, his legs spread as wide as humanly possible. He’s faceless so we can’t be sure, but from what we can surmise, he’s staring confidently at the viewer with a good dose of flirtatious swagger.  

It’s amusing to think that former U.S. president John F. Kennedy and his handlers had likely seen de Kooning’s image of Porter, among others, when they selected her to paint his official portrait for the Harry S. Truman Presidential Library & Museum in Independence, Missouri. Truman apparently wanted a portrait of the president to hang there, and de Kooning’s dealer at the time, Robert Graham, had a personal connection to Kennedy’s brother Joseph Jr., and arranged the commission. According to de Kooning’s account of the arrangement, she was selected, in part, because she had a reputation for painting quickly, and the president never sat still for long. But as Curtis writes in her biography, “Elaine’s freely brushed style must have seemed an ideal way to reflect the essence of The New Frontier—the forward-looking, aspirational leitmotif of Kennedy’s presidency.”

De Kooning flew down to Kennedy’s “Winter White House” in Palm Beach, Florida, to sketch the president from late 1962 through early 1963. Recounting the experience in ARTnews in 1964, she described him as “incandescent, golden. And bigger than life. Not that he was taller than the men standing around; he just seemed to be in a different dimension.”

He was the ultimate male subject, and de Kooning labored over the portrait for months, producing dozens of sketches and paintings in her brushy, gestural, semi-abstract style. He was certainly not faceless, and she struggled to accurately capture his features and character while conjuring something beyond his public persona. “She felt desperate to have achieved such small success, and she had the feeling of always being on the verge of an artistic breakthrough that continually eluded her,” writes Simona Cupic in the National Portrait Gallery’s catalogue. But when Kennedy was shot in November 1963, she stopped working for nearly a year.

By that time, however, de Kooning had completed her portrait of the president, which was acquired by the Truman Library. (It now resides in the JFK Library and Museum in Boston.) It is the most formal of the bunch, but it was probably also the most contemporary presidential portrait America had ever seen. Kennedy, who is seated, looks up while turning a page of a book in his lap, as though the artist casually caught him off guard while working. He leans in, suggesting a sense of familiarity with his portrait painter, and while de Kooning has clearly described the features of his bronzed visage with loving detail, most of the picture is more abstract, formed by the artist’s rapid-fire, angular brushwork. The president appears immersed in lemon-yellow strokes, incandescent, as she had described, and glowing with the optimism of the era.

Although she’d established herself as a writer and artist a decade before painting Kennedy—enough to include her very visible “EdeK” signature at the bottom of the work—“the commission really turned the tide,” says Curtis. Life magazine commissioned a story about her painting the late president and hired photographer Alfred Eisenstaedt to shoot her in the studio, surrounded by images of him. For perhaps the first time ever, Elaine de Kooning’s name was as recognizable as that of Willem de Kooning. But as Fortune has pointed out, her husband’s influence was always an asset, not a threat. “She would tell people that instead of working in his shadow, she painted in his light,” he says.