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Photo by Pete Souza
*On Feb. 12, Amy Sherald’s painting of Michelle Obama was unveiled at the National Portrait Gallery, alongside Kehinde Wiley’s portrait of President Barack Obama.
Both Sherald and Wiley were interviewed and chosen for the job by the Obamas.
As the former first lady revealed, “She came in and she looked at Barack and she said, “Well, Mr. President, I’m really excited to be here and I know I’m being considered for both portraits, but Mrs. Obama ..’ — she physically turned to me, and she said, ‘I’m really hoping that you and I can work together.'”
Journalist Alex Wagner asked Sherald, “You maybe had a particular interest in painting her?”
“Yeah!” she laughed. “I mean, [Mr. Obama] was asking questions as well. And she was like, ‘Shhh, no, no, no, no, no.’”
Amy Sherald, 44, has gone from being a virtual unknown to one of the most talked-about artists in the world. After having waited tables and taken out loans, painting Mrs. Obama was her big break.
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Wagner asked, “Tell us how game-changing this moment is.”
“I am relieved that I can pay back my school loans,” Sherald said.
“Becoming an artist is not empirical; it’s not about hard work. You have to put the work in, but that doesn’t mean you’re going to make it. I think, hustling for that long, it kind of, like, chips away at your self-esteem. And then, the breakthrough comes, and you’re like, ‘Oh, yeah, that’s who I am. Like, this is who I am!’”
The portrait is similar to Sherald’s other works, except her models — exclusively black and never smiling — are usually strangers she meets on the street, per CBSnews.com.
She described her process of working with Michelle Obama: “We had two sittings. But you’re still always a little bit nervous, having to look her in her eyes, ’cause I have to study the face before I photograph to try to figure out what I want, and those little intense moments where you just have to have courage to keep looking, because you get bashful because, you know, you’re looking at the first lady!”
Why does she paint black skin in grayscale?
“It just looked good, the gray skin on these bright colors,” she said. “I think, also, I was subconsciously struggling with not wanting to be marginalized. And I say that because I feel like the black body is a political statement in itself, right? So, on canvas all of a sudden I’m making a political statement just because I’m painting brown skin. But, I paint the way that I paint. And she chose me, she knew what to expect.”

“There are some people who look at the portrait of the first lady, and they say, ‘I don’t see her in it. I don’t see the Michelle Obama that I know.”
Sherald said, “Everybody is invested in [the Obamas] in all kinds of ways, on all different levels. And so, for me to even want to paint her makes me crazy. Because I’m setting myself up for criticism, right? I feel like I captured her. When I look at it, I see her; I see the Michelle that was present at the sitting, you know, a contemplative, graceful woman who understands her place in history.”
Today, Sherald’s paintings — which she works on in her Baltimore studio — are now selling for up to $50,000 each.
“We don’t even say the word ‘waitlist’ here anymore. There’s not even a waitlist, we just say there are conversations to be had,” said her Chicago gallerist Monique Meloche. The gallery has reportedly been fielding around 50 inquiries a day since the Obama’s portraits were unveiled.





















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