Rudolph Burckhardt, “Elaine de Kooning” (1960) (courtesy Estate of Rudy Burckhardt and Tibor de Nagy Gallery, New York. © 2014 Estate of Rudy Burckhardt / Artists Rights Society (ARS), New York)

WASHINGTON, DC — While at the retrospective of Elaine de Kooning’s portraiture here at the National Portrait Gallery, I recalled reflections by the late figurative painter Sherman Drexler at his loft in Newark a couple of years ago. “You paint your desire, you paint your passion,” he said.

He was speaking about his free-spirited New York comrades in the 1950s, including his friend Elaine. By today’s technocratic standards and philosophical artists’ statements, Drexler’s observation seems refreshingly naïve — and interestingly subversive.

Undoubtedly, Elaine de Kooning, who worked mainly in portraiture, painted her desire. Her passions ran toward people. And that’s whom she painted. This massive exhibition —astutely organized by the museum’s chief curator, Brandon Brame Fortune — pays special attention to art as progressive, demanding lifework. It tracks Elaine de Kooning’s development as a first-rate, innovative portraitist through variously sized drawings, figure studies, trial sketches and small paintings across five decades, with each room dramatically highlighting the best of her large-scale oil paintings, some never exhibited publicly until now.

The exhibition creates a narrative trajectory that will undoubtedly surprise those who assume they know all there is to know about the downtown New York art scene in its heyday. And the show offers uninitiated visitors a chance to discover an American artist who redirected techniques of twentieth-century vanguard painting into a form of portraiture that is as much about the rhythms and processes of human recognition as it is about the diverse characters who were her subjects.

Elaine Fried was born in Sheepshead Bay, Brooklyn, in 1918 and, by many accounts, inherited her mother’s fierce wit and independence of mind. She left the small town of Brooklyn and resettled in downtown Manhattan in the late 1930s, taking art classes at the Leonardo da Vinci School and earning money from odd jobs, including a stint as a fashion model. Before long, she was pretending to be rooming with longtime friend Ernestine Lassaw after she’d met, taken classes from, fallen in love and shacked up with a struggling Dutch immigrant artist named Willem.

Elaine de Kooning, “Willem de Kooning” (c. 1952), oil on panel. Board: 38 5/8 x 25 1/2 x 1/2 inches Frame: 50 x 36 5/8 x 3 1/2 inches. National Portrait Gallery, Smithsonian Institution (© Elaine de Kooning Trust)

Married in 1943, the couple survived most of that decade living hand-to-mouth. After a detour in Provincetown, two summertime stints at Black Mountain College and with neighbors and friends like George Balanchine, Tennessee Williams, Rudy Burckhardt, and Merce Cunningham, the couple were at the eye of a cultural hurricane that was already making landfall.

With her passion for people, Elaine was by inclination a portraitist. But she was equally drawn to experimental art forms as the Abstract Expressionist movement unfolded before her eyes, inside her very home. Outside, the new Modernist gospel was being spread in Art News and other influential magazines by the couple’s good friends Thomas Hess and Harold Rosenberg.

In the 1940s, she divided her output somewhat neatly between abstract pictures and realistic portraiture. Two captivating early self-portraits indicate that she quickly intuited how she could rework the latter’s naturalistic demands. “Self-Portrait” (1942) is dominated by browns, tans, and yellow, capturing the young artist in a pose that conveys lithe elegance and bohemian tenacity. Her brown eyes are flecked with splintered lights apparently from an indoor source, and she stares back so wide-eyed that it isn’t until you’ve noticed her raised brows and the pensive clench of her jawbone that you realize she’s looking warily beyond you, as if into a destiny she seems pretty sure will become whatever she wants it to be.

Elaine de Kooning, “Self-Portrait #1” (c. 1942), oil on Masonite. Stretcher: 23 × 17 3/8 inches. Frame: 31 7/8 × 26 1/4 inches. Michael and Susan Luyckx (© Elaine de Kooning Trust)

Though less psychologically complex than the earlier work, “Self-Portrait” (1946) is an early career masterpiece. Adapting some of Cubism’s geometric severities and objective pictorial planes to lifelike ends, the painting depicts the painter in her studio, dressed in a cerulean blue smock and gazing up from a sketchbook. Objects in the background — a blue vase on a pink table, a white teacup on the floor, an abstract Native-American-inspired textile on the wall — pull our attention away from the artist’s face toward the edges of the composition. She seems to be dramatizing her young self as a girlish woman inhabiting an urban fairy-tale, Alice in a Downtown Wonderland.

Her struggle to integrate abstraction into realistic portraiture was underway soon enough. In the show’s companion monograph, critic Ann Eden Gibson argues convincingly that the portraits Elaine de Kooning made of the painter Joop Sanders in the mid-1940s prefigured her later inventions and pivotal breakthroughs.

The Dutch-born Sanders, a friend of the couple’s and a fellow Abstract Expressionist in New York, sat for about a dozen different portraits and portrait studies, through which Elaine tried out every possible species of modernism. The exhibition’s monograph contains Cezanne-like renditions of Joop, the German Expressionist-inspired “Joop-Mephisto” and “Joop-Pink” (1946), and even a phantasmal, Chagall-like “Joop & Milton’s Girl” (1946).

In one exemplary drawing included in this show, Sanders’ melancholic young face is rendered realistically, but from his neck down, through irregular outlines of his shoulders, arms and hands, the drawing bristles with barely contained expressionistic impulses.

Elaine de Kooning. “Joop Sanders” (c. 1946), graphite on paper. Sheet: 16 3/4 × 13 3/4 inches. Collection of Clay Fried (© Elaine de Kooning Trust)

Straight lines elide and then cut into the jacket’s folds and creases. Sanders’ head, his densely shaded cravat, and the sculptural tangle of his folded hands carry equal pictorial force in the portrait’s midsection. Yet each of those three focal points is positioned successively further to the right, threatening to throw the composition off balance. In a countermeasure, the central image of the young man’s chiseled jawline, narrow face and straightforward gaze operate like ballast against the portrait’s wayward momentum.

The Joop series seems influenced by the aloneness and androgyny that Picasso infused into his own earliest portraits. In this painting, Sanders is depicted in semi-silhouette, his pale face delineated with a clean, classical simplicity. The luminosity of his face seems like sacred deference to his melancholic introspection. Here and in other early drawings and paintings, Elaine captures likenesses by evoking the tentativeness and spontaneity of a sudden, intimate recognition.

The concept of the “glimpse,” a buzzword also favored by her husband, can be a key to understanding Elaine de Kooning’s strategies as she moved into the 1950s. In Betty Jean Thiebaud’s Elaine de Kooning Paints a Picture (1976) a short documentary included in the exhibition, she talks about capturing that momentary, multitudinous cascade of visual impressions within which the act of recognition occurs. “If you saw your father blocks away,” she says, “you wouldn’t have to see any details, you just would recognize him. I’m interested in that element, whatever it is, that you see in a glimpse.”

And her ability to paint this glimpse may explain her paintings’ intentional “absences,” as discussed by critic Ann Eden Gibson. Gibson claims, in her penetrating essay, that Elaine de Kooning deliberately and variously integrated into her portraits incomplete features and implicit cognitive gaps. According to Gibson, she did so to generate an invisible, evocative vortex of sorts in each portrait, within which (as Roland Barthes claims happens in portrait photography) three human subjectivities can merge in a visual continuum – that of painter, sitter and viewer.

Call it what you want — “ecstatic intersubjectivity” is my own pretentious name for it — but whatever it was, it raised her game considerably.

By the early 1950s, the muted browns of ashcan realism and the stabs at high modernism are replaced by exuberant experimentation with non-naturalistic colors and an interest in reproducing the interplay between strong light, sartorial fashion, and human form. It suddenly looks so alive and so American.

An “instant illumination” is how she named this new objective, and as she found it, she hit a stride that would sustain the rest of her career.

In “Conrad Fried” (1954), her brother sits upright with his eyes closed, hands folded, legs unevenly extended, and his elongated feet shod in orange loafers. She cultivates her brother’s distinctiveness in such a way that this electrifying composition mimics the flickers of personal recognition happening in real time.

These effects occur by a multifocal design. First our gaze is drawn to the unstable intersection of the riotous backdrop with its yellow, and red, olive lines, and then to the delineated, illustrative arrangements and squares that represent the apparel enfolding his individualized proportions. Yet our attention is also pulled upward, to Fried’s semi-abstract, meditative face, where an intangible tranquility seems to flow outward, coursing through his firm posture. Nowhere is Elaine de Kooning’s competing drives toward abstraction and figuration more theatrically played out than in this portrait and its companion piece, of similar scale, “Peter Fried“(1956).

Like characterization in a novel, what she leaves out of the portraits becomes as important as what she puts in. The most famous example of this intentional game of hide-and-seek is, of course, her epochal “Frank O’Hara” (1962). During the late stages of its making, out of frustration, she erased the features of the poet’s face — believing, quite rightly, that once those facial details were replaced by just a fleshy pink smudge, O’Hara’s individuality would emerge more resoundingly from her depiction of the poet’s inimitable body language: the louche, lean frame; the pointy shoulders; the right hip pressing into his long, straight right arm; the fingers of his left hand barely hooked into the pocket of his beige chinos. Frenetic colors pass upwards and downwards around him, but rather than detract from the portrayal’s originality, the setting’s dynamism invites us to glide round and round the figure’s form, enriching our comprehension of the rendition.

Elaine de Kooning, “Fairfield Porter #1” (1954), oil on canvas, Kemper Museum of Contemporary Art, Kansas City, Missouri. Collection Bebe and Crosby Kemper (© Elaine de Kooning Trust)

This face-effacing technique, combined with an abstractly painted backdrop, had been mastered earlier, and less self-consciously, as in her massive painting, “Fairfield Porter” (1954). The broad-shouldered maestro of landscape and still life painting sits upright in a gray suit and red-and-blue striped tie. His large, masculine frame dwarfs the thin wooden chair so conspicuously that you can virtually feel that weight and bulk. His long legs are spread-eagled, his knees are bent at slightly divergent right angles, and his large hands dangle idiosyncratically near his inner thighs. It is portraiture as intimate panorama, a lustrously colored, high-octane composition coalescing from its pieces into a robust, patrician physicality that must have been quintessential Fairfield Porter.

Another sustained, life-sized glimpse of overt masculinity is “Harold Rosenberg #3” (1956) in which the influential critic sits in an easy chair dressed in a rumpled tuxedo. The painting’s realism evolves from the meticulously black-painted outline, a careful formalism exemplified in the companion drawing included in the exhibition.

Elaine de Kooning, “Harold Rosenberg and Willem de Kooning (c. 1956), pencil on paper. Sheet: 18 1/8 x 22 1/8 inches. National Portrait Gallery, Smithsonian Institution (© Elaine de Kooning Trust)

A seam running from the shirt runs down Rosenberg’s torso and disappears into his crotch. His long, extended legs, crossed at the ankles, project aggressively forward, as if jutting out of the frame. Rosenberg’s individuality materializes from many features all at once — the pursed lips and manicured mustache, signifying an intellectual sangfroid, the cocksure recline of his bulky frame, registering a tired, art-celebrity’s comfort through an after-party nightcap, and the magical precision with which the artist has rendered his fingers as they clutch a can of beer in one hand and gingerly hold a lit cigarette in the other. The non-naturalistic coloring then immerses Rosenberg in an untidy haze of rust, orange, gray, green and brown.

In “Edwin Denby” (1960) the dancer-poet fills the narrow frame like some salt-of-the-earth Brahmin, a Manhattan flâneur of unobtrusive charisma, all conveyed in his owl-like eyes, his dark eyebrows offset by his dome of silver hair, his sinuous arms and thin, tapered legs. Outside flourishes of vertical and gold lines, running parallel to his limbs, elongate him further. In an exhibition with plentiful portraits of cool cats, Denby’s prowl seems the most effortless.

By the late 1950s, as evidenced in the show’s midpoint, Elaine de Kooning had carved out an artistic reputation distinct from her husband’s. Willem was by then a giant player in the New York and East Hamptons scenes, already close to becoming what he arguably remains to this day – the most accomplished and innovative American painter of the twentieth century.

At this time, after having begun to move in separate social orbits, the couple drifted even further apart, and in 1957, they officially separated. In addition to cross-country teaching gigs, Elaine de Kooning had become a leading writer on contemporary art – combining a practitioner’s knowhow with a romantic’s enthusiasm, a pedigree that could have sustained a side career if she had decided to become a full-time critic.

But even in her rare leisure time, she was too busy painting her desire. She could never consider abandoning art for other pursuits. Her artistic passions were at full boil and converging with political groundswells. It was the dawn of the 1960s. At the very beginning of that decade, she took up the anti-death penalty cause, mainly through social activism around the case of Caryl Chessman, a death-row inmate who argued his innocence through a series of bestselling books. She even painted the convict’s portrait before his execution.

And then Kennedy’s Camelot called on her. The portraitist was about to tackle her most problematic subject yet.

Next week: Elaine de Kooning in the 1960s and after.

Elaine de Kooning: Portraits continues at the National Portrait Gallery (Eighth and F Streets NW, Washington, D.C.) through January 10, 2016.

Tim Keane's writing on poetry and visual art has appeared in Modern Painters, The London Magazine, Utne Reader, The Brooklyn Rail, Vision China, and in Joe Brainard's Art (University of Edinburgh...