Amy Sherald spent years painting in obscurity, and almost died from a rare heart condition. Now 52, the artist behind Michelle Obama’s official portrait is one of America’s most celebrated painters.
When Amy Sherald was selected to paint the official portrait of Michelle Obama eight years ago, many people in the art world didn’t know who she was. They do now. At 52, Sherald has become one of America’s most celebrated painters. She’s had two major museum retrospectives this year and was supposed to have a third this month at the Smithsonian’s National Portrait Gallery. But Sherald canceled it, concerned, she says, that museum officials, already under pressure from the Trump administration, were going to try and censor a painting. The controversy made headlines, but Sherald has faced much bigger challenges than that. Like many of the people she paints, Amy Sherald has found a way to make her way.
In Amy Sherald’s paintings, her subjects — Black Americans — stare silently straight out from the canvas. There is something in their eyes that draws you in, something knowing in their gaze. They appear unapologetic, unafraid, posed against monochromatic backgrounds, or in scenes as bright and bold as they are. In this painting, a farmer leans atop an impossibly pristine John Deere tractor, surrounded by blue sky and green grass.
Anderson Cooper: In so many of your paintings the subject is looking out at the viewer.
Amy Sherald: I think that’s important, I don’t think these portraits are confrontational, but they are present. And they do want you to sit with them and have an exchange.
Amy Sherald: They have jobs. They’re doin’ their jobs, you know? They’re being beautiful, they’re being colorful. But they also have work to do in the world.
Anderson Cooper: And they’re doing that work in your painting?
Amy Sherald: By standing there and being present, and looking at you, and meeting your gaze. That’s the work.
Amy Sherald: They don’t have to say anything. But every time you look at that portrait, something is happening inside of you.
Amy Sherald’s work hangs in the most prestigious museums in America, and in the rooms of major collectors, and some smaller ones, including me. This summer she gave us a private tour of her show “American Sublime” while it was at the Whitney Museum of American Art in New York, home to some of the greatest artists of the 20th and 21st centuries. Sherald has been dreaming of having a show here for years.
Amy Sherald: I would sit in my studio every day. And I would meditate and visualize myself in this space.
Anderson Cooper: How does it compare to the fantasy?
Amy Sherald: It’s exactly like it.
Anderson Cooper: Is it?
Amy Sherald: Yeah, it’s perfect.
Her paintings are portraits, but not in the traditional sense. The people in them are real, but their names are rarely used. She’s cast them in a visual story all her own.
Amy Sherald: The process starts with a photograph. After I randomly come across some person that, I like to say, like, my energy recognizes their energy, or there’s something there, right? They come to the studio and either I already have a vision in my head of what I wanna create, or they are the walking vision of what I want to make. And I photograph them.
She’s used friends, models, dancers, strangers she’s seen on the street. The clothes they wear are often thrift store finds. Sherald has racks of them in her studio.
Amy Sherald: I’ve had this for probably five years. Just waiting for the right person.
There were only two paintings in Sherald’s show of people whose names were used. This is her portrait of a very alive Breonna Taylor, painted after she was shot to death by police in 2020 in a botched raid on her apartment. And this is Sherald’s most famous work, the former first lady titled “Michelle LaVaughn Robinson Obama.” Unveiled in 2018, it made headlines around the world.
Anderson Cooper: Did you know how important this was going to be for your career?
Amy Sherald: Yes.
Anderson Cooper: Did you think about that?
Amy Sherald: I think in the moment I wasn’t thinking about that. Because if I did I probably would’ve just freaked out, you know? I just stayed outta my head and stayed in the painting.
Anderson Cooper: What stands out to you?
Amy Sherald: When I look at it now? The dress. Like, I’m deeply in love with this dress. Just the red, the pink, the yellow, and then the black and gray.
