Growing up, Isaac Benigson would make an annual pilgrimage from London to South Africa with his parents to visit family friend Hylton Nel, a reclusive, extraordinarily talented ceramics artist. Nel’s house was filled with paintings, books, and historic artifacts, all of which eventually found a way of influencing his art. This stuck with Benigson, who started sourcing inspiration from his surroundings to make his own art.

In high school at Halcyon London International, Benigson began to develop his voice. “I had this friction with my art teacher,” Benigson remembers, “because I had this burning thing of making these portraits, and it was becoming quite repetitive. And I was saying, I’m going to do this until it’s out, until it’s finished.”

Mildred, the work that got Isaac Benigson accepted to the Royal Academy’s prestigious Summer Exhibition, was drawn on a pizza box.

The portraits Benigson was obsessing over in his early teens have since become his calling card. “At the very beginning I was inspired mainly by John Waters,” says Benigson of the filmmaker whose subversive art is often a composite of high and low culture. “In a similar vein, I made this drawing on a pizza box called Mildred.

Innocent, Impressionistic, and well observed, the portrait was accepted into the Royal Academy’s prestigious Summer Exhibition, the world’s oldest open-submission show, in 2019 to much success. A postcard of the work, sold in the gallery’s gift shop for the duration of the show, became one of the summer’s best-sellers. “That absolutely changed my life,” Benigson, who is now 20, says.

Doing portraits allows Benigson to give voices to his subjects.

In January of last year, Benigson had his debut solo exhibition, “Calendar Girls,” at the Chandler House, a gallery, shop, and studio in Cape Town known for hosting monthly shows by established and emerging artists. Still in high school when the show opened, Benigson became the gallery’s youngest artist ever.

Of his work, Benigson says, “I suppose the portraits can be considered versions of myself or versions of my mother or amalgams of people that I know.... I suppose it gives me a space to perform, you know, perform these people out. And give them voices.”

Benigson’s second solo show, “The Ladies of Chiltern Street,” opened at London’s Shreeji News, the magazine shop and café run in partnership with AIR MAIL, in October of last year. Hosted in the downstairs events space, the exhibition showcased a new series of the artist’s brightly colored portraits.

One of Benigson’s portraits at London’s Shreeji News, the site of the artist’s second solo exhibition.

A frequent Shreeji customer, Benigson noticed that he “often encountered the same people, on the streets or coming out of the nearby Chiltern Firehouse or buying a magazine,” he says. “There’s a whole kind of world that spins around there in a funny way.”

The Shreeji show was a hit. “I had an Instagram message from this mad air hostess and her husband, who wanted a family portrait of the two of them with their dog,” he says. And the messages kept coming: “You know, ‘Please paint my mother.’ And then I paint these people’s mother and they’d get very angry and say, ‘You’ve destroyed my mother.’ And then I’d have to change them.”

Looking ahead, Benigson is preparing to start his second year of the theory-based course Culture, Criticism, and Curation at Central Saint Martins, and hopes to focus more on his own imaginative work than on commissions for picky customers.

Bridget Arsenault is the London Editor for AIR MAIL