Amy Sherald on her portraiture, her subjects’ gaze, and the impact of painting Michelle Obama’s portrait
Amy Sherald's Artistic Vision: Portraiture, Presence, and the Michelle Obama Legacy
Bizeconanalysis.com – This is an updated version of a story first published on Oct. 19, 2025. The original video can be viewed here.
Rising to Prominence
Nearly a decade has passed since Amy Sherald was chosen to create the official portrait of Michelle Obama, and the art world has taken notice. At 52 years old, Sherald has emerged as one of the most honored painters in America today. Her recent accomplishments include three major museum retrospectives held last year alone. Yet one particular exhibition from last autumn captured widespread attention when Sherald made the unexpected decision to cancel it. Museum officials, reportedly under pressure from the Trump administration, were believed to be attempting to censor one of her paintings.
As we first reported last October, Sherald has navigated challenges far greater than institutional censorship. Like many of the individuals she chooses to portray, Sherald has discovered her own path to success and recognition.
The Power of the Gaze
What makes Sherald's work distinctive is the way her subjects—primarily Black Americans—stare silently and directly from the canvas. There is something profound in their eyes, a knowing quality in their gaze that draws viewers in. These portraits appear unapologetic and fearless, posed against monochromatic backgrounds or within scenes as vibrant and bold as the subjects themselves. In one notable 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.
A Dream Realized
Sherald's work now hangs in the most prestigious museums across America, in the rooms of major collectors, and in the collections of smaller ones, including Anderson Cooper himself. Last summer, she provided a private tour of her exhibition "American Sublime" while it was displayed at the Whitney Museum of American Art in New York—a venue home to some of the greatest artists of the 20th and 21st centuries. Sherald had 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.
The Creative Process
Her paintings are portraits, but not in the traditional sense. The people depicted are real individuals, yet their names are rarely used. Sherald casts them within a visual narrative entirely her own. The process begins with a photograph. After randomly encountering someone whose energy she feels she recognizes, she invites them to her studio. Sometimes she already has a vision in mind; other times, the person becomes the walking embodiment of what she wants to create.
Sherald has worked with friends, models, dancers, and strangers she has spotted on the street. The clothing they wear is often sourced from thrift stores, and she maintains racks of these garments in her studio. She has kept certain pieces for approximately five years, simply waiting for the right person to wear them.
Two Named Portraits
Only two paintings in Sherald's exhibition featured subjects whose names were explicitly used. One is her portrait of Breonna Taylor, painted after the young woman was shot to death by police in 2020 during a botched raid on her apartment. The other is Sherald's most celebrated work: the former first lady titled "Michelle LaVaughn Robinson Obama." Unveiled in 2018, this portrait 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. I wanted the dress to also have some kind of symbolism, and almost be a painting in and of itself.
Before arriving at the Whitney, "American Sublime" was displayed at the San Francisco Museum of Modern Art. Sarah Rober contributed to this report.
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