I also always wear a hat.
"I still remember, back in the '60s," Tom said, "when I was director of the Brooklyn Museum and you were on the board, all the other trustees came to the meetings in an overcoat and you wore a parka. Today you're nicely dressed, but you're wearing sneakers. It gives you a boyish look. It's also a screw-you look: ‘You may think I'm a preppy, but I'm a different kind of preppy.'"
My portrait, we agreed, would be of medium size—not the large whaling-captain size—and would be vertical, ending above the waist. "The first decision is always about where," Tom said. "I figure out where things are going to go on the canvas—it's like a line map—and where the contrasts are going to be. The usual tendency is to start with the eyes because they demand the most attention; we communicate with our eyes. When I was a kid my father advised me to ‘Start with the eyebrows; then you'll know where the eyes should go.' There's no basis for that whatever. In your case the eyes are not as important as where the necktie is going to be, because that necktie, against the white shirt, is the strongest contrast in the picture."
We tried different poses, Tom taking a digital photograph of each, until we found the one we liked best—the body slightly tilted to the right, the head tilted slightly to the left. The photograph of that pose, greatly enlarged, would be Tom's point of reference when he did the painting. Portrait painters have used photographs as an aid since the days of Thomas Eakins, in the late 19th century, and today they paint almost exclusively from photographs; 21st-century man is too busy to sit still for an artist. But Tom likes to paint from life as often as he can. "A photograph doesn't have presence," he said. "A person is a living, changing, evolving thing—which is much more exciting."
"The first thing I have to do," Tom said, "is to make a compositional sketch: this is where the head goes. The shape of the head and the way we carry it on our shoulders are the essential elements in recognizability. You'd recognize me from the back, a block away, by my silhouette. The most important job for me is to achieve a shape that you'd be recognized from: What is the essence of you? The biggest part of your likeness is the shape of your head, the length of your neck and your posture—not your eyes and nose and other features."
He showed me some one-minute pencil sketches he makes at airports and in meetings—widely different men and women. "I know a lot about these people," he said. "They all have a distinctive head shape, and each one carries it on the neck in a characteristic way. Remember Audrey Hepburn, how lovely she was? It was partly because of the way her very long neck positioned her head."
The photographing done, we called it a day and went out to eat; I would start sitting for my portrait in the morning. Actually, Tom didn't call it a day. At dinner he was still working, studying my smallest move.
When I reported for duty the next morning, Tom, consulting the photograph, had situated my portrait on the canvas, which he had already painted gray-green. It was an outline drawing, simple as a comic strip, but even in that primitive form the finished portrait was visible. Now Tom was ready to start on me. He sat me on a stool and put the photograph beyond me—"quite far away," he said, "because I only want to use it to get the sitter's body language, not the details. I don't think you can build a portrait out of details.
"For me, portraits fall into two general groups," he explained. "One is about a moment in time—a situation in a specific context. The other is about a person alone.
"The first category is epitomized by Sargent's painting of a woman reading to a boy. That's the specific context. If you signed up for a portrait by Sargent, you signed up for 60 sittings; it could take more than a year. Children really sat, and often they clearly would like to be somewhere else. That kind of portrait can also include furniture or clothes, or catch a gesture or a fleeting smile. Sargent really captured those incredible moments.