Artist Amy Sherald on what's behind her subjects' eyes in portraits

This is an updated version of a story first published on Oct. 19, 2025. The original video can be viewed here.

When Amy Sherald was selected to paint the official portrait of Michelle Obamanine 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 had three major museum retrospectives last year. But it was another exhibition last fall -- at the Smithsonian's National Portrait Gallery - that made headlines. Sherald cancelled it -- fearing museum officials, under pressure from the Trump administration, were going to try and censor a painting. As we first reported last October, 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. Last 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 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.

Her paintings are portraits, but not in the traditional sense. The people in them are real, but their names are ra