The man raises Southern charm to an art form as he explains, with modesty and a few cigarettes, the evolution of his paintings, which create a gallery inside his yellow colonial-styled house in western Henrico County. The house and garden are still-life perfect, evidence of a strong collaboration between Gregory and his wife, India, who are raising two sons — both excellent critics, the artist adds — in this visually rich setting. India Gregory’s portrait, painted by her husband, graces a wall near the front door, possibly making eye contact with a portrait of him hanging opposite, which was painted by his mother when he was 2.
Portraits are something Claiborne Gregory has become noted for. His likenesses of former Gov. George Allen, former Lt. Gov. John Hager and numerous other public figures are noteworthy commissions. The artist makes a point of capturing particular facial expressions that reflect the subjects’ personalities — a duck hunter with a great grin, card-playing buddies in their characteristic poses around the table. Gregory, extroverted and mannerly, brings diplomatic and observational skills to the relationship between portrait painter and client. The intent is never to shock, always to please, he says.
Equally significant in Gregory’s repertoire are the paintings of sporting scenes, landscapes, and maritime settings, including a striking oil of the Arch of Carsaig in Scotland. There are historical pieces, pastoral views and many paintings that capture a swirling vortex of water as it moves through a passage. Gregory puts human figures in most of his paintings to demonstrate scale, and also because his connections to other people are a driving force.
He is, even when away from the canvas, always processing the visuals, thinking through the resolution for each painterly question that arises as a piece builds. Though he is self-taught, he is also self-educated about the painters whose work he most admires: John Constable, J.M.W. Turner, Rembrandt. “To me, they are the teachers I didn’t have,” Gregory says. “I ask myself, how would Winslow Homer have solved this? You think of the forces of nature, of what you’re trying to get the viewer to see, and how to take the abstract to the real.”
Gregory is not one to leave the outcome to chance. Each large painting evolves from a series of studies and notes. In some cases, clients want to buy all of it — a paper trail of perhaps a dozen items that culminates in the work itself. He paints about 20 finished pieces a year.
“I’m ambitious for it and I live for it,” Gregory says. “I want people to enjoy my paintings, and part of my job is to figure that out. The other reward is an ego trip, I guess. Painting is ego-driven, the admiration, the excitement. And it’s grand fun.”