Before Sheila Culbert’s farewell presentation to the alumni on June 8 during Reunion Weekend, she and Robert Anderson ’64 unveiled a portrait that Bob painted of Sheila, the school’s seventh head of school.  

Two dogs and a book are part of the painting, fitting since Sheila is a dog lover and an avid reader. And fitting since Bob remembered visiting Sheila in her office in Founders Hall, where it was clear her dogs were a big presence.   

“It is important to build relationships with people,” Bob says of his process. “I don’t spend a lot of time having people sit for me. A lot is photographs and composites, but it is very helpful to spend time with the subject of a painting, get to know them a little bit, have dinner with them, spend the night where they live, whatever it might be to find out what makes them tick. That informs the process in a way that is essential.”  

Bob has painted hundreds of commissioned portraits in his career, including the official portrait of President George W. Bush for the National Portrait Gallery of the Smithsonian Institution in Washington, D.C., and one for the Yale Club of New York City; portraits of former Governors William F. Weld and Edward J. King for the Commonwealth of Massachusetts; and former Federal Reserve Chairman Alan Greenspan for the Federal Reserve Board headquarters in Washington, D.C. Bob and George W. Bush were classmates at Yale, both graduating in 1968. When painting the former president’s portraits, Bob spent time at Camp David, the presidential retreat in Maryland, and at the Bush family home in Texas.   

Bob says he is patient, determined, and disciplined when working on a portrait.   

“In the beginning it was intimidating, but I am well past that,” he says. “I have been at it for 50 years now, so I am well past the point that I think I am going to be stuck before I even start. That doesn’t mean it is all smooth sailing, that I can go start to finish without making any errors or any adjustments. It is constantly putting strokes down, deciding whether they belong there or need to be wiped out or painted into. The whole thing is fluid. Constant adjustments.”  

Then there comes a time when the portrait is nearing the finish.  

“It’s like the little engine that could,” Bob says. “You're going up a hill and you're getting close to the top. You’re still putting a lot of effort into it. Then, all of a sudden, you go over the peak, and you know you’ll be home. Even if the engine cuts out, you’re in the direction you want. And in the end, there is a point — I call it an ah-ha type of moment — when the character on the canvas draws a breath. I can feel it. I don’t hear it, but I know it’s happened.”  

There also is a moment of recognition when he puts a highlight in the subject’s eye. “There is recognition between the eyes looking at you and my looking at the person, and I know I have the likeness I am after because it becomes that person to me,” he says.  

Bob’s portrait of President Bush for the National Gallery was based off of photographs taken by a White House photographer at the time. The former president, says Bob, was “congenial and comfortable” in those photos. 

“I saw in the photographs the person I knew, and I think I captured that in the portrait that is in the National Gallery,” Bob says. “I think people perceive it in a way that, no matter what your political interests or persuasions are, he is looking comfortable and relaxed and is that kind of person.”  

Bob was in the National Gallery at one point when a group was being given a tour and the guide was talking about the President Bush portrait. Bob stood back, took it all in, and after the group had moved on, he told the guide who he was. “She said. ‘Oh, my goodness, can I get my group back and would you be willing to talk about it?’” Those visitors were in the right place at the right time.  

Bob says he was interested in drawing even when he was a child. He did some illustrations for the Loomis yearbook and for The Loom, the school’s literary publication. He also doodled in the margins of notebooks while in English class sometimes. “I never took an art class here,” he says, “which is kind of ironic.”  

After graduating from Yale, he went into the service, with a stint in Vietnam. When his tour of duty ended in 1972, he was trying to figure out what would be next. “I did love to paint and draw, and I came back to that,” Bob says. He entered art school in Boston. “I figured I’d take the lid off my head and let whatever it is in there out, and see if there is something in there I could make a career of.”    

And what a career it has been. By 1981 he won the First Prize in the National Portrait Seminar Competition in New York City. He produced portraits of the “Breck Girl” for the Breck Shampoo ads in the 1980s, and the U.S. Postal Service contracted him in the 1980s to produce portraits for stamps in the Great American Series, including that of Sitting Bull. Bob's work hangs in various buildings in New England and beyond, ranging from the Connecticut State Capitol to the Boston Public Library and New York Presbyterian Hospital.  

Bob's portrait of Frederick Torrey, head of school from 1967 to 1976, hangs in Founders Hall. As with any portrait, there is a story behind it.  

“As a rite of passage when [Fred] was growing up, anyone in the family when they got to be 10, 11, or 12 had to do a solo summit of Mount Monadnock [in New Hampshire],” Bob says. “And he said, ‘I’d really like to have Mount Monadnock in the background of the painting. I said, ‘How about this, how about the next time you go to the top of Mount Monadnock, you just scrape up a little stuff from the ground up there, and I'll mix it with the paint, and there will be the real thing at the top of the mountain.’”  

Fred obliged.  

“He sent a package with a label on it that said ‘true grit,’ so there was real Monadnock earth at the top of the mountain in the painting, and the rest was stapled to the back of the painting, I believe.”  

Reunion Weekend is a time to share stories and catch up with others. Bob was celebrating his 60th Reunion. When he passed through Grubbs Quadrangle, he likely couldn’t help but think of a memory from when he was a senior.  

As the story goes, there was a bit of a rivalry between dorms. Bob and his buddies would launch water balloons from their senior porch in Warham Hall trying to hit friends across the quad on a Batchelder porch.  

“Occasionally they made it all the way across, but usually they didn’t,” Bob remembers. “And on one occasion we didn’t see who was coming down the [senior] path. It was the headmaster, Frank Grubbs, and the balloon missed him but not by much. You never saw seniors clear the deck faster.”