Amy Sherald's Painting of Michelle Obama Went Viral. But She's No Overnight Success.

There’s a clatter of traffic on the street outside the Baltimore warehouse where portraitist Amy Sherald has her studio, but approach her space and music rises over the din.

It’s the last day of February, and Sherald, who until recently was little known outside certain art world circles, has just unveiled one of the most anticipated portraits in decades, an enormous canvas of Michelle Obama now on view in Washington, DC’s National Portrait Gallery. With it, Sherald has committed to the record not just her vision of one woman, but a promise: that there will be more like Obama, that the progress she represents remains possible.

It’s a message that is clearly registered by a little girl who, the day after Sherald and I meet, stands awestruck in front of the painting because, as her mother explains when the image goes viral, “she believes Michelle Obama is a queen and she wants to be a queen as well.” Within a few more days, the museum has to move the portrait into a larger space, the better to accommodate the crush of visitors.

So, of course, the music Sherald has queued up is Beyoncé. Hers is a Beyoncé moment.

SHE AND BEYONCÉ HAVE THIS IN COMMON: THEIR TALENT IS EXCEPTIONAL, BUT NEITHER OF THEM PUSHES SOME FICTION OF EFFORTLESSNESS. CREATION IS HARD.

Ever since the Smithsonian announced it had commissioned the artists Kehinde Wiley, 41, and Sherald, 44, to paint the Obamas’ presidential portraits, Sherald’s rise has been spun into the stuff of children’s tales. It’s true that she received a heart transplant at 39, just under a decade after she was diagnosed with congestive heart failure. She lost her father at 28. Her brother died in 2012. But she is not Cinderella, and her success is not good fortune. Sherald and Beyoncé have this in common: Their talent is exceptional, but neither of them pushes some fiction of effortlessness. Creation is hard.

“I know what people want to hear,” Sherald says, sitting on a sleek couch beneath the 900-square-foot studio’s enormous windows. “‘She almost died, and three years later, with barely any work, this happens.’ That’s a complete lie.” Sherald—who beat out 2,500 entrants to become the first woman to win the Smithsonian’s prestigious 2016 Outwin Boochever Portrait Competition, who has had solo shows at the Monique Meloche Gallery in Chicago and the Reginald F. Lewis Museum in Baltimore, and who opens her first major solo show at the Contemporary Art Museum St. Louis in May—is calm but resolute: “I’ve hustled for 15 years.”

Sherald grew up in Columbus, Georgia, the daughter of a homemaker and a dentist who wanted her to pursue a career in medicine. Instead, she studied painting at Clark Atlanta University and received her MFA from the Maryland Institute College of Art in 2004, where she began developing the interpretation of traditional portraiture that she uses today—one that draws from the genre’s conventions (and omissions) but also from sources as varied as vintage textiles and the Panamanian landscape.

It’s individual people, though, who inspire her the most. Both she and Wiley, who paints his sitters in poses that recall the European old masters, seek to situate blackness within the art historical tradition. But Sherald doesn’t crown her muses. What she elevates is ordinariness: Women who arrest her. Men whom she approaches on the street and beseeches, “Let me photograph you.” Each is a faithful depiction, in a sense, but Sherald is not interested—as the photographer Dawoud Bey once wrote in a prescient piece about her work—in “a meticulous restatement of the facts.”

Instead, Sherald, who envisions black skin in pale shades of charcoal and accents it with vivid clothes and accessories, is committed to reinterpretation. (She dressed Obama in a gown from the American brand Milly, the pattern evocative of both the painter Piet Mondrian and the quilts of beloved black women artisans in Gee’s Bend, Alabama.) It’s that balance between the fantastic and the real that sets Sherald apart, notes Dorothy Moss, a curator at the National Portrait Gallery. She commands “a certain hopefulness” in her work. In both their pose and their demeanor, her sitters look forward.

Sherald doesn’t characterize her subjects’ mood—she’d rather let viewers decide for themselves—but she does want her portraits to be “mirrors and reflections for people to see themselves in.” Her aim is to release those she paints from a world that evaluates them by their skin, to insulate them from “the gaze of other people.” When asked if it was this sensibility that appealed to Michelle Obama, who handpicked her for the work, Sherald declines to comment. But she grants, with a grin, that the collaboration “just makes sense.” As Obama told the crowd at the event, “There was an instant connection, a kind of sister-girl connection” with the painter.

"THE LOOK THAT AMY PAINTED WAS SO POWERFUL AND SO TRUE TO MICHELLE. I HAD SEEN THAT LOOK ON HER FACE BEFORE."

Kate Capshaw, the actress and philanthropist who, with her husband, Steven Spielberg, helped fund the Obama portraits, said that at their reveal, it was clear that the women had come to understand each other. “The look that Amy painted was so powerful and so true to Michelle,” Capshaw says. “I had seen that look on her face before.”

Not all were so sure. After the portrait was unveiled, Twitter exploded with criticism. People didn’t think the portrait looked like the Michelle they knew. They didn’t like how Sherald had painted Obama’s skin—in her characteristic palette, this time with luminous taupe undertones. They didn’t appreciate that they couldn’t make sense of Obama’s expression, one that contained hints of both judgment and grace.

“IF I HAD PAINTED THE FIRST LADY FOR INSTAGRAM, IT WOULD’VE BEEN A DIFFERENT PORTRAIT.”

Sherald admits that the backlash hurt, but hours into the portrait’s dissection, a friend reached out to her with this succor: “Amy, some people need their poetry to rhyme.” Sherald grows quiet for a moment, then adds, “If I had painted the First Lady for Instagram, it would’ve been a different portrait.”

For with this monumental commission, Sherald has herself been reinvented. To have been chosen for this has made her stand with her “back a little straighter.” She put her career on hold to care for sick relatives. She waited tables to make ends meet. She overcame heart failure. She didn’t survive all that just to fade into insignificance. Sherald, who was recently picked up by the powerhouse gallery Hauser & Wirth, doesn’t use words like “fate,” but she believes in the power of sequence. “All the delays that I’ve had in life, all the years that I’ve lost—I’ve landed here just on time.”

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