Fourteen years ago Aaron Shikler was commissioned to paint a portrait of two small children who lived at an exclusive address on New York’s Fifth Avenue. Their mother approved of the work and asked the artist to paint portraits of her as well. “She would smile a great deal,” Shikler recalls of the sittings that followed, “but she was nervous, tense, high-strung. There was tragedy in those eyes.” Then, as work on the second portrait continued, the young widow announced that she had decided to remarry. Her new husband would be Aristotle Onassis. “It was like a load taken off her,” Shikler remembers. “She became gay and happy and smiling and kittenish, a totally different woman.” Yet Shikler didn’t make any change in the painting, which was already earmarked to hang in the White House. “A portrait should be a visual biography at a certain time in a person’s life,” he explains. “I went after that haunted look because that was the Jackie Kennedy I wanted to represent.”

Ultimately, Shikler’s philosophy has been vindicated—at least in the marketplace. Though the artist himself maintains that Andy Warhol’s position in the pantheon of Pop Art makes him “the preeminent American portrait painter of the period,” Shikler’s agent, New York gallery owner Roy Davis, vigorously disagrees. “Aaron has not made himself accessible,” he says. “He does not seek out the avant-garde, and he is not a guest at SoHo painters’ parties. But he will do 90 percent of the important portraits to be done in America.” With fees starting at $25,000 for a head-and-shoulders and $35,000 for a full-figure painting, Shikler, 59, can limit himself to eight or 10 portraits a year and still enjoy a substantial six-figure income.

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If Shikler has become, in the words of one critic, “the Gilbert Stuart of the jet set,” he owes at least a portion of his fame to the Kennedys. Perhaps even better known than his painting of Jackie is his posthumous portrait of the late President that hangs in the White House. The work was authorized by his widow. “The only stipulation she made,” says Shikler, “was, ‘I don’t want him to look the way everybody else makes him look, with the bags under his eyes and that penetrating gaze. I’m tired of that image.’ ” Shikler started making sketches from photographs, but all were unsatisfactory until he came across a picture of Ted Kennedy at JFK’s grave with his head bowed and his arms crossed. “My God,” he remembers exclaiming to himself, “that’s a perfect image!” Because Senator Kennedy is physically a much bigger man than his brother was, Shikler had to scale down the figure. When Jackie saw the sketch, she chose it over several others at once. “Let’s do this one,” she instructed the artist.

Not unexpectedly, both Kennedy portraits provoked controversy when they were unveiled at the White House in 1971. And when Shikler was later commissioned to do the posthumous painting of Robert Kennedy that now hangs in the Justice Department, Washington Post columnist Maxine Cheshire cattily suggested it was because “[he] is the only artist to paint the Kennedys as they see themselves.” Some critics accused him of romanticizing Jackie and making her somewhat stubby hands long and slender. Others complained that his JFK portrait was a somber memorial ill suited to its place at 1600 Pennsylvania Avenue. Shikler scoffs at both charges. “In the case of the President,” he says, “all I wanted was to portray a man who looked like he could think.” As for the criticism, he adds, “I said the hell with it. Mrs. Kennedy loved the idea, I loved the idea, and it certainly stands out among all those God-forsaken postage-stamp portraits hanging in the White House.”

Such arguments are academic, of course, while Shikler’s success in attracting clients is not. Among the public figures who have sat, or stood, as his subjects are Lady Bird Johnson (for the LBJ library in Austin), heart surgeon Michael DeBakey (for Houston’s Baylor College of Medicine), CBS President William Paley, Jordan’s Queen Noor (for whose portrait King Hussein paid a reported regal $140,000) and singer Diana Ross and her three children.

The son of a Polish immigrant pants contractor and his wife, Shikler was born in Brooklyn, and decided as a teenager to find his future in painting. Admitted to the first class ever to attend Manhattan’s selective High School of Music and Art, he later won a scholarship to Temple University’s Tyler School of Fine Arts. After serving in Europe in World War II as a map-maker, Pfc. Shikler returned to Tyler for two degrees, then studied in New York for three years with the famed Abstract Expressionist Hans Hofmann. “I wasn’t a starving young artist for the simple reason that I had a highly supportive family,” Shikler says. “They didn’t understand a bloody thing I was doing, but they knew damn well I wasn’t going to be a doctor or a lawyer or a teacher, so they helped.” In gratitude, he has established a Frank and Annie Shikler Prize at the National Academy of Design. Following the death of his mother in 1976, he began signing his works Aaron Annie Shikler, though his given middle name is Abraham.

By the early ’50s Shikler had concluded he could never express himself adequately in Abstract Expressionism, then the preeminent movement in art. “Creatively,” he says, “I found that I could make sense only as a representational artist.” He was married by then to Barbara Lurie, a fellow student at Temple. “I saw this young thing lying near a tennis court,” he recalls, “and it looked as if there was a bug on her neck. I went to wipe it off. It turned out to be a mole.” To support her and, eventually, two children, Shikler began delivering up to three portraits a month. His first breakthrough came in 1959, when he was given a commission by the wife of industrialist Charles Engelhard. Jane Engelhard went on to become a major patron, eventually commissioning the Lady Bird portrait as well as one of Mike Mansfield for the U.S. Senate, and another of the Duchess of Windsor.

Sustained by such assignments, the Shiklers live now in a cavernous 10-room apartment on the Upper West Side of Manhattan. Though they recently bought a country house on Long Island, they remain addicted to the cultural life of the city. At 52, Barbara (nicknamed “Pete”) works as a reference librarian at the New-York Historical Society, while daughter Cathy, 25, is an art historian and son Clifford, 20, studies painting. Wednesday nights Shikler enjoys a busman’s holiday by teaching an art class with his close friend David Levine, the caricaturist, his co-tenant in a spacious studio that overlooks Broadway.

Through the years, of course, both Shikler and his art have changed. “When I was very young,” he recalls, “I wanted to please, and it was a disaster.” Once, he remembers, a pudgy, balding client insisted that Shikler highlight the few strands of hair he had left. “So I redid the painting to show them,” says the artist. “The man was apoplectic. The new pose made him look even more jowly.” Chastened by such experiences, Shikler is no longer so accommodating. “Any worthwhile portrait must start out as a painting,” he says. “The person posing for it is secondary. Most portrait painters do it the other way around, striving primarily for the likeness—which is why there are so many bad portraits being done.” Shikler now refuses to paint subjects against cluttered backgrounds because he believes that “beautiful light, flickering shadows and textured materials suck viewers in. I want a more stark approach, to show what my subjects are about.”

His austerity is not always appreciated. Shikler’s portrait of the late financier Robert Lehman, which hangs in the Lehman Pavilion of New York’s Metropolitan Museum, was painted against a plain, neutral background. Fulminates New York Times critic Hilton Kramer: “[It’s] the worst portrait by a contemporary artist that has been done. It’s slick, it’s without any strong pictorial character, it’s standard boardroom-anonymous.” A former Met curator, on the other hand, praises Shikler for creating “a kind of blueprint of what that person was at the time he was painted. Years from now, you will know the subject by his clothes, his stance, his attitude.”

Shikler’s commissions buy more than the artist’s skills and his signature; they also buy his time. He takes from six to 18 months to complete a portrait, partly because he prefers to have several works in progress at all times, and partly because he refuses to rush. Typically, he devotes considerable time simply to achieving a sense of his subject. “I do studies,” he says, “with the idea of getting not so much the personality, but a sense of the coloration. Then I take masses of photographs and lay them out on the studio floor. These sort of speak to me, telling me what kind of poses might work. Then I draw from these photographs, and finally I design what I want on the canvas.” Only then does he ask a subject to pose in person, striving mightily to keep him at ease.

“Some painters want you to sit there rigidly holding the pose,” says Shikler. “That’s the worst thing you can do, because it comes through in the portrait.” Shikler keeps up a line of casual chitchat, and plays classical music throughout a sitting. “But when I was in Jordan doing Queen Noor,” he recalls with a laugh, “I discovered there was nothing classical on the radio. There was Arab music, which is fine for five minutes, or American pop, which is even worse. One day I was fiddling around with the stations and I got what sounded to me like classical music, so I locked it in.” Gradually Shikler realized the queen’s entourage was abuzz. “It was Hebrew music, from Israel,” he says. “I said, ‘I’m sorry, but I need it to work.’ ” Protocol suffered, but the station stayed on.