The Great Painted Portrait Artists

Courtesy Stone Roberts

For legacy or vanity, portraits still hold great appeal. Departures looks at five artists who are bringing the tradition into the 21st century.

At least once every decade, it seems, the art world stokes the old debates about whether painting is dead, whether figurative painting is hopelessly retrograde or suddenly sexy. But the painted portrait—a mainstay since Renaissance times—never goes out of fashion, thanks to that irrepressible human desire to be immortalized in a work of art. Even after photography came along and changed everything with its democratizing accessibility, the painted portrait remained something special: the intimate exchange between artist and subject, the meticulous rendering of the sitter onto canvas, the uniqueness of the finished object. After all, unlike photographs, no two paintings are exactly alike.

These days commissioned portraiture is generally seen as a commercial art world niche, and dedicated portrait painters tend to work outside the contemporary gallery system. Sometimes represented by brokers or dealers of more academic realist art, they often rely on word of mouth and their own social networks to find clients. These five New York painters, in various stages of their careers, are some of the most respected practitioners in this specialized field—sought after for their unique ability to capture something essential and unmistakable about their subjects.

Bradley Livingstone Black

As a premed student on a golf scholarship at Duke, Bradley Livingstone Black took a course on the anatomy of the lower extremities. “We got to dissect a cadaver,” the Canadian-born artist, now 32, recalls. “Nobody else wanted to touch it, but I was dazzled. I could see the light hitting the tendons like rainbows.”

Though he abandoned his medical aspirations early on, Black remained enamored with the wonders of the human form. “I love the body—men, women. I can see why architects talk about ‘the figure.’” He took a painting class his senior year and went on to get an MFA in sculpture at the classically oriented New York Academy of Art. It was during his graduate studies that he began doing portrait commissions.

These days Black—who plays golf less often (“It’s a very visual game and, when you get to a certain level, really creative,” he says)—works out of a studio in a glass-walled building on the Lower East Side. His recent portraits include a monumental equestrian painting of the Infanta Elena of Spain, the king’s eldest daughter, a commission that arose from a discussion she and Black had at a dinner party about her unsatisfactory experiences with artists. Black depicted the princess in a simple gray riding jacket atop her horse (the artist, as it happens, is also a rider), with a royal residence in the background. The finished painting now hangs in her home in Madrid, alongside Black’s portraits of her two children, Felipe and Victoria.

By his own admission something of an overgrown kid himself, Black says he especially enjoys painting children. Last year he did a pair of sunny portraits of two young brothers from a prominent Cuban-American family that show the boys, all blond hair and dressed in double-breasted topcoats, posed against plain backgrounds. One is “kind of shy but smiling,” the artist notes, while “the other guy is more pensive, sort of like me when I was a kid.”

An admirer of the Old Masters (he likes to quote Ingres: “If you can draw, you can paint”), Black references contemporary art as well. The sibling portraits, which are painted on separate canvases so the boys can each have his own one day, are intended to hang flush together, “with this strong red Barnett Newman stripe along the side, unifying them,” he says.

Though Black usually paints from photographs, he feels it’s essential to spend time with a subject. “You have to have an interest in psychology,” he says. “A lot of people don’t like to sit anymore, but I’m not wired that way. I like everyone’s unique history.”

Black’s drawings (charcoal, graphite, chalk, pastel) start at $10,000 and his oil paintings at $25,000. Contact him at or go to


Hilary Cooper

I was in my Matisse mode,” Hilary Cooper says with a laugh, discussing her 2008 portrait of Jane Brown Grimes, the first female head of the United States Tennis Association. Cooper had asked to paint Grimes in a knee-length cherry-red coat she’d worn when presenting Roger Federer the champion’s trophy at the U.S. Open. Commissioned by Grimes’s father, Hazard Gillespie, éminence grise of the law firm Davis Polk, the portrait is typical of Cooper’s bright, spare-as-all-New-England style. Depicting Grimes seated in an upholstered armchair, the picture conveys her athletic prowess and inner strength.

Cooper, 52, is a popular portraitist in her three home bases—New York City, Aspen, and Lakeville, Connecticut—and she prides herself on being able to draw out even her most reluctant subjects. “I like being with people,” she says. “I’m not one to sit alone. It’s a joy to portray another person. It’s a privilege, and it suits me.”

During her previous life, in leveraged buyout financing and corporate cash management, Cooper took classes at the Art Students League. As commissions began to accumulate, she quit banking in 1987 to paint full-time. Cooper, who has done portraits of a number of high-profile figures, says many commissions arise from—and lead to—friendships. Her portrait of Louis Begley, the distinguished lawyer and author, for example, came about after they got to know each other at a club they both go to. Another portrait, of Oliver Dobbs (now a CIO at the London hedge fund CQS), was a 40th birthday gift for his wife. Cooper later painted her as well, and a close friendship now exists among them all.

An avid skier, Cooper came to what she considers her most meaningful portrait series after a near-tragic accident on the slopes in which she broke her neck. While on the mend she turned to painting people with physical disabilities in works she calls “Divided Portraits.” These two-part paintings usually consist of a head-and-shoulders portrait paired with one that reveals the subject’s handicap, such as a view of his or her lower body and legs in a wheelchair. A book on the series, published in 2007 by Umbrage Editions, includes an introduction by the founder of Very Special Arts, Jean Kennedy Smith.

Cooper enjoys the challenge of developing a rapport with her sitters, be it a prickly Ed Koch, now one of her biggest fans, or a restless Peter Matthiessen, the novelist, adventurer, and Zen master whom Cooper painted in his priestly rakusa. “I reminded him that he sits still for forty-five minutes at a time when he meditates,” Cooper says. “So much of portraiture is an abstraction of visual experience—the process of discovering who someone really is.”

Cooper’s prices range from $10,000 for a head-and-shoulders portrait to $25,000 for a full-length. Contact her at 917-225-7085 or, or go to


Byron Dobell

Perhaps unsurprisingly for an artist who had a diverse, decades-long career as an influential magazine editor—at Esquire, New York, and American Heritage—Byron Dobell insists he doesn’t have a signature painting style. “I can do it freely, like a Frans Hals, or precisely, like a Bronzino,” says the artist, who shows his work locally at the W. M. Brady Gallery. “It’s always a balance between the line, tone, and mood.”

Dobell, 83, still paints five days a week in a studio in his Upper East Side home. An affable raconteur, he counts numerous members of New York’s media elite among his colleagues and friends. A number of them have sat for him over the years: Betty Friedan, Gay Talese, Dominique Browning (“I first painted Dominique as a young girl, for her parents,” Dobell says), Tom Morgan, Clay Felker, and others. His portrait of Felker, wearing a light-colored suit almost natty enough for Tom Wolfe, was acquired last year by the National Portrait Gallery, which already owns the Friedan.

Growing up in the Bronx, Dobell wanted to be an artist, but his Lithuanian immigrant father and American mother couldn’t support that financially impractical route. Eventually, however, his success in journalism brought him back to art. In the early sixties the inimitable caricaturist David Levine, who had done magazine assignments for Dobell over the years, invited him to join an informal group of realist painters for weekly studio sessions led by Levine and the renowned portraitist Aaron Shikler.

Dobell’s commissions began to take off after he donated a portrait session to a fund-raiser at his daughter’s grammar school, where he eventually painted such students as novelist Anne Roiphe’s daughter Katie, herself now an established writer. Word spread, and since then generations of New Yorkers have sat for him.

“Each time I paint I get to know someone new,” says Dobell, who on average requires six hours of sittings for a portrait. One of his recent commissions was painting the youngest daughter of Pulitzer Prize–winning biographer Stacy Schiff. It was a project that generated a lot of stimulating conversation, says Dobell, adding, “It’s a great way to make a living.”

Dobell charges $5,000 for a head portrait, $10,000 for a half-length. Contact him at 212-861-0256.


Stone Roberts

Stone Roberts is not being immodest when he says, “People generally want a painting of mine first. Then they want to be in it.” Coveted by collectors and included in numerous museums, the Yale- and Tyler School of Art–trained artist, 59, is best known for his lapidary still lifes, luminous street scenes, and intricate, moody interiors with figures. Betsey, his wife of 36 years, is a frequent model (“a great beauty,” Roberts says), as are friends and neighbors in the Beaux-Arts Belnord building on the Upper West Side and in Stonington, Connecticut, the couple’s weekend retreat. While Roberts’s figurative paintings are portraits of sorts, he only occasionally does portrait commissions by special request.

One of his first, Roberts says, was for Thomas McNamee, the author and environmentalist, and his wife, Louise. That portrait’s skillful serenity and balanced precision evoke the Dutch masters Roberts admires: Louise, wearing a striking red business suit, is absorbed in some papers beside her on the floor, while her husband peers intently at a computer monitor on the bureau behind her. When the McNamees divorced, the artist retitled the canvas Portrait of a Marriage, emphasizing the scene’s undercurrent of detachment.

Roberts works on a large scale but meticulously, creating Renaissance-style cartoons in ink and chalk for his paintings, incorporating “a formal idea and usually a mythical and psychological element,” he says. Perhaps because his work is so full of allusions, it tends to appeal to literary-minded collectors such as Carll Tucker, a retired magazine and newspaper publisher now active in philanthropy, and biographer and cultural patron Barbara Goldsmith, who commissioned Roberts to paint her grandchildren.

Roberts was an obvious choice to do the portrait of the William A.V. Cecil family, descendants of George Washington Vanderbilt who live near the Biltmore Estate in Asheville, North Carolina. A native of Asheville, Roberts has been a friend of the family since he was a boy. Commissioned for the centenary of the Gilded Age landmark, in 1995, the painting lavishly presents the family in a great room with sweeping views of the estate out the windows; on the wall behind the group is Seymour Joseph Guy’s famous 1873 portrait of the original owner and his brood. Roberts notes that “the little boy in the Guy painting is William Cecil’s grandfather.” The two works now hang on opposite walls in the Biltmore’s sitting room. The trick, Roberts says, “was to capture people who are very private in a painting that has a public function. The funny thing about this one was I had to go back and add a child and a pram, because the family kept getting bigger.”

Roberts does few portrait commissions. His portrait drawings start at $15,000 and his interiors with portrait figures at $175,000. Contact him at 212-787-0620 or, or go to


Sacha Newley

During a visit to Sacha Newley’s disheveled studio in the Machine-Age Starrett-Lehigh Building on Manhattan’s far west side, the artist was putting the finishing touches on a likeness of Ed Ruscha, one in an ongoing series of portraits of fellow painters that includes Ross Bleckner and Hunt Slonem. Done in Newley’s signature style, which marries classical composition with expressionistic brushwork, the series is something of a departure from the literary and Hollywood subjects—Gore Vidal, Christopher Reeve, Oliver Stone—he had been known for.

The son of Joan Collins and the late actor Anthony Newley, the 45-year-old artist was born in New York and spent his early childhood in Hollywood. But after his parents’ divorce (his 2008 Self-Portrait with Happy Family recalls the period before their split), he moved with his mother to England, where he eventually studied briefly with the realist painter Lance Richlin. For the most part, however, Newley taught himself by looking at the masters and exploring various subjects, from landscapes he painted in coastal Lyme Regis to the self-portraits he began in 1985. His passion for portraiture, he says, originated in a very personal place—his father’s face. “It was so expressive. I loved to watch it as a kid. Later I grew fascinated by what faces hid from me.”

Based in New York since 2000, Newley often travels to his clients’ homes, where he makes sketches and takes photographs to use as references for the finished portrait. “I sort of morph into another person when I’m in another place,” the artist says. “I even dress differently”—a blazer and cashmere, say, as opposed to the color-stained khakis and Obama baseball cap he was wearing in his studio the day we met.

Newley, who likes to imagine a rebirth of “the kind of society portraiture John Singer Sargent painted with such depth,” had just returned from several sittings in Palm Beach with Nadege Kalachnikoff, the wife of antiques dealer and decorator Lars Bolander. She wanted a portrait for her sons, now in their thirties, “to have when she’s gone,” the artist says. Newley was also recently commissioned to paint Charles and Clo Cohen, the bicoastal real estate developer and his wife, who have lately become prominent society figures. “They were much younger than I expected, and such fun,” Newley says. Portraiture, he adds, “is very social.”

Newley’s prices start at $10,000 for a head-and-shoulders portrait. Contact him at 917-459-7707 or, or go to

Commissioning a Portrait

Finding a portrait artist is not a daunting secret rite. Many sitters use the Portrait Society of America ( as an initial resource, or they turn to well-known firms like Portraits, Inc. in New York ( or the Portrait Group in Washington, D.C. ( Such businesses represent a large number of portraitists who work in various styles, and they provide the convenience of one-stop shopping while making all the arrangements. But since they take a commission, they tend to charge more. Hilary Cooper, whose clients come mostly via word of mouth, has a standard pricing formula. “I list my prices on my website,” she says. “$10,000 for a head-and-shoulders, $15,000 for a three-quarter-length portrait, $25,000 for a full-length.” These sums are roughly typical for an established portraitist (depending on the work’s size), while big-name painters like Aaron Shikler or Jacob Collins can command three or four times as much. Most artists prefer a minimum of four to six hours of sittings, often broken up into a few sessions. If this doesn’t suit a client’s busy schedule, artists will often request an initial sitting, then work from photographs to complete the painting.