How Kehinde Wiley’s Dazzling Portraits Won Over the Art Market

When former U.S. President and First Lady Barack and Michelle Obama revealed they would be commissioning two young African American artists to paint their official portraits, the news hardly came as a surprise. The Obamas, after all, had burnished a reputation for identifying and uplifting rising talent, from the sartorial to the literary, and now in the visual arts. The selection of Barack Obama’s portraitist, —an artist who recontextualizes classical European portraiture by inserting contemporary people of color into vividly lush backdrops—signaled that the 44th president’s depiction would radically depart from his forebears. When Wiley’s portrait of Obama was unveiled in 2018, the world marveled at an image that portrayed the former head of state in all of his humanity. And Wiley, whose meteoric rise to success had been largely institutional until then, became an international household name overnight.

“Many collectors tell me that even when their kids’ friends come to the house and see a Kehinde Wiley painting on the wall, they all know who that is,” said Roberts Projects co-owner Bennett Roberts, who has worked with Wiley since 2003. “That’s an amazing thing.”

Wiley enjoyed a vaunted career even before he was selected to immortalize President Obama. His large-scale portraits of everyday people, often Black men—subjects he meets on the street, photographs, and then inserts into reimagined scenes drawn from classical paintings—represented a new tradition of Black portraiture when they emerged from Wiley’s studio at the Yale School of Art, and propelled the artist to a coveted residency at the Studio Museum in Harlem. That experience would wind up landing Wiley several solo exhibitions, including one at the Brooklyn Museum when he was still in his twenties. Between continuously showing both domestically and internationally—Wiley is represented by galleries in New York, Los Angeles, Paris, and London—and a mid-career retrospective, “A New Republic,” that has traveled to six different U.S. cities, the market for Wiley’s work remains insatiable. The artist’s studio produces about 20 paintings per year that typically sell for prices in the six- to seven-figure range, while at auction they have yet to surpass $400,000.

Though Wiley’s appeal can partly be attributed to meticulous technique, he also illuminates a persistently troubling treatment of Black bodies in American life, applying a sensitive and admiring gaze to his figures. Wiley’s subjects, often donning streetwear popularized by hip-hop culture, are frequently posed according to biblical iconography or amid mazes of flora in the style of classical portraiture. Valerie Cassel Oliver, curator of modern and contemporary art at the Virginia Museum of Fine Arts (VMFA), who worked closely with Wiley on the institution’s acquisition of his bronze monument Rumors of War (2019), traced his interest in transposing Black figures into classical European portraits to his childhood.

“Growing up in Los Angeles, his mother was very focused on [Wiley and his twin brother] having a sort of expansive view of the world, so she would take them to a lot of museums,” Cassel Oliver said. “He saw so much beauty in these classical portraits, so grand and monumental, but the thing that really stuck with him is that no brown or Black people were presented within the portraits. He knew people who were powerful, he knew women who were graceful. He knew women who were dignified.”

Enrolling in art classes at the age of 11 at the behest of his mother, Wiley eventually went on to study at the San Francisco Art Institute before being admitted to Yale, which has a reputation for churning out promising young art stars. Almost immediately upon graduating, Wiley was offered a residency at the Studio Museum.

“The Studio Museum residency was certainly a huge milestone, and it’s always been a capstone for a young artist,” Cassel Oliver said. “There’s nothing more incredible than artists having resources of time and money and place to really experiment.”

Christine Kim, the curator who presided over Wiley’s residency, introduced him to Julie and Bennett Roberts. “There were always three artists that made it into the Studio Museum residency, but she said to us, ‘There’s one particular one I want you to see,’” recalled Julie Roberts. “And we made our way up to Harlem and into his studio. Right off the bat, it was different than anything we’d ever seen up to that point.”

The pair was immediately interested in working with Wiley, who already had multiple offers from dealers around the country. They nonetheless managed to land an exhibition with their gallery at the time, Roberts & Tilton, because Wiley was eager to show in his native Los Angeles. His first solo show at the gallery, “Pictures at an Exhibition,” sold out before it opened, with six-foot-tall portrait paintings fetching sums in the low five figures. Eighteen years later, prices for Wiley’s paintings have risen substantially, with works regularly commanding six figures on both the primary and secondary markets. In addition to paintings—which make up about 80 percent of Wiley’s market—the artist also produces drawings and sculptures.

Julie Roberts said that, even before the Obama portrait, the award of a U.S. State Department Medal of Arts by then–Secretary of State John Kerry in 2015 allowed Wiley’s thriving market to really take shape internationally, increasing the demand and value of his work. “We not only worked on a commission for the U.S. Embassy in Santo Domingo, Dominican Republic, but also loaned works to U.S. embassies all over the world,” she said. Additionally, the collaborative spirit among the galleries that represent him—including New York’s Sean Kelly, London’s Stephen Friedman, and Templon in Paris—has allowed each of them to focus on specific components of Wiley’s career.

With runaway market success coming early in his career, it didn’t take long for Wiley’s works to start appearing on the auction block. “What I think is really interesting about Kehinde Wiley is that he’s had institutional support from the get-go,” said Rebekah Bowling, a senior specialist and head of day sales at Phillips. She noted that works with “a direct historical reference” tend to fare best at auction.

His earliest secondary-market sale was in 2005 at Christie’s, where the painting Saint Francis of Paola (2003) garnered $33,600. Fifteen years later, his auction record is more than 10 times that: Portrait of Mickalene Thomas, The Coyote (2017) sold at Phillips for $378,000 in December 2020. The work came from the collection of Virginia philanthropists William and Pam Royall, longtime collectors who played an instrumental role in the VMFA’s acquisition of Rumors of War, a monumental bronze statue that directly engages with an international conversation around monuments and representation.

“Our attraction to Wiley’s work was a matter of recognizing the importance of portraying Black men and women in a ‘spectacular’ fashion that was not present in art history,” Pam Royall said in an email (her husband recently passed away). “Given the time and the subject matter, Bill and I believed very strongly that Rumors of War belonged in Richmond—and at the VMFA specifically—and that it could play an important role in the healing that is so necessary as we strive to empower all Virginians.”

Special projects like Rumors of War, his ambitious Black Rock artist residency in Senegal, and upcoming solo exhibitions—Roberts Projects will host a show of new works in 2022—continue to place Wiley in dialogue with the themes that have driven his practice from the outset, and have rendered him a beacon of Black liberation.

As Cassel Oliver put it: “Wiley is really always trying to shift the perception of how Black bodies should exist in society, demanding that people see that so that hopefully perceptions can shift. He is in a long line of Black artists who have endeavored in portraiture—, , and so many others—who have worked toward an evolution of what portraiture can be.”