Artist Spotlight: Amy Sherald and the Hard Work of Simply Being

By Tim Gihring

June 16, 2025—For the past few months, in the opening gallery of Mia’s “Giants: Art from the Dean Collection of Swizz Beatz and Alicia Keys” exhibition, two men have been popping wheelies. Their dirt bikes are angled skyward. One man holds on with a single hand, the other man has let go entirely. There is no ground beneath them, no buildings or horizon, only the blue of sky, as though these two young Black bikers have managed to defy the gravity of everyday life.

Amy Sherald painted them in 2022 on two enormous canvases, facing each other, a diptych she called Deliverance. They were part of the urban dirt bike scene in Baltimore, which Sherald came to know while studying for her MFA in the early 2000s. The bikers—mostly people of color—would ride in rambunctious pelotons, weaving through traffic and, well, popping wheelies. 

“Most people consider them a nuisance,” Sherald says in a new video about these paintings and their subjects, “but I think there is something so fantastic about their ability to teach themselves these highly skilled ways of riding these dirt bikes. A lot of times their hands are off the bike. There’s a sense of freedom.”

Recently, when Baltimore began cracking down on the riders, Sherald posted an image of her diptych to social media. “I remain in awe of their skillz,” she wrote.

Sherald earned her MFA in 2004 and struggled for years afterward. She had largely formed her style, depicting Black Americans in vibrant outfits but grayscale skin tones, to emphasize personality over race. “Resting places,” she calls her paintings, where Black people can let down their guard and “see a reflection of themselves that is not in resistance or contention.”

But critics were slow to recognize their quiet power. 

“At first, I saw her work as very high-level illustration,” says Jerry Saltz, New York magazine’s longtime art critic.

In 2016, Saltz served on the jury for a National Portrait Gallery competition, which Sherald had entered. She was in her early 40s but still virtually unknown. At night, she was waiting tables. 

Saltz took a photo of her entry and sat with it for a while. “I stared at the pic I took and realized that her figures were aware, had autonomy and attitude, and that the way she painted the Black skin a sort of pewter or slate gray grisaille gave her paintings a singular, surreal, very commanding presence.” 

Saltz nominated her for the top prize, and she won. This spring, when Sherald’s “American Sublime” solo exhibition opened at the Whitney Museum of American Art, the New Yorker magazine ran her prize-winning portrait on the cover. Miss Everything (Unsuppressed Deliverance), she called it, an image of a young Black woman with a bright red flower in her hat, confidently holding an absurdly large teacup.

The Michelle Obama Effect

Less than a year after her win at the National Portrait Gallery, Sherald found herself on a very short list with a long, storied history—as one of the nominees to paint either the president or the first lady. In this case, the Obamas.

At their first meeting in 2017, Sherald told them, “I know I’m being considered for both portraits, but Mrs. Obama, I’m really hoping you and I can work together.” Michelle Obama felt the same way. 

Compared to Kehinde Wiley, Barack Obama’s choice to paint his portrait, Sherald was still a relative newcomer. But her portrait of Michelle, in a white dress with blocks of color reminiscent of pop art and Gee’s Bend quilts, arguably made the bigger splash. In the two years after its unveiling at the National Portrait Gallery, attendance doubled. 

These days, she works in New Jersey, directly across from Lower Manhattan. Her studio is as restful and immaculate as her art, paint tubes neatly hung on a wall with clips, outfits for models lined up on racks.

She’s frequently above it all, on scaffolding, working across massive canvases. As her reputation has grown, so have her works—they are some five times larger now than before the Obama portrait. Still intimate but arresting.

Now she’s happy to let the work do the talking. In 2012, a health condition caught up to her: She was walking into a Rite Aid in Baltimore and collapsed. Her heart had given out, and by the end of the year she had a new one. The heart transplant, she says, not only gave her a new lease on life but a new personality. More subdued. Not pushing it.

Recently, however, as politics has pushed into the art world, Sherald has found herself pushing back. This fall, “American Sublime” is set to move from the Whitney to the National Portrait Gallery. The museum is part of the Smithsonian, ordered by the Trump administration to remove “divisive, race-centered ideology” from its work. Simply showing Black Americans for who they are, Sherald acknowledges, is getting harder. 

“Painting Black figures, whether I want it to be or not, it’s political,” she told National Public Radio this spring.

“Now I feel like every portrait that I make is a counterterrorist attack, to counter some kind of attack on American history and on Black American history and on Black Americans.”

That said, her approach isn’t likely to change. If anything, she says, it’s more important than ever.

“This work has to speak to not only people that look like me but also sit in the world for all of us to understand.”

More About “Giants”

Learn about the exhibition, on view at Mia through July 13, 2025, including visitor guides, playlists, and upcoming events.