DARIEN, Conn. — On the first day of Operation Iraqi Freedom in 2003, Robert Anderson ’68 began work on his first portrait of George W. Bush ’68, former president of the United States and his former classmate.

As he laid out the painting that would later hang in the Yale Club of New York, Anderson could not imagine that five years later the president would call him the “good and forgiving friend” he needed to render a second portrait for the National Portrait Gallery in Washington, D.C.

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The painting, which was unveiled on Dec. 19, 2008 at a private ceremony in the gallery, depicts the president in a more personal, more conversational manner than the painting hung at the Yale Club, Anderson said.

“It seemed to me like a really courageous way of portraying the man — very honest and forthright — as the people who know him and like him and care about him would experience him,” Anderson said of his approach.

The key criteria of portraiture on display in the museum’s Gallery of Presidents tends to be portrayal of an accurate likeness, akin to a photograph, said Samuel Messer, the associate dean of the Yale School of Art. Nonetheless, Anderson said, he tried to capture the feeling one would have conversing with the president, departing from the formality of his predecessors.

The painting has a classic composition for the informal feeling Anderson aimed for, Messer said. His hands are placed calmly, and the relaxed shoulders brings the viewer’s eyes into the picture, past the subject, to the flowers, he added.

“It is a great example of how a portrayal can be used to convey a message about the ‘kind’ of person the painter and the sitter desires,” Messer wrote in an e-mail to the News.

‘A Way About Him’

At the painting’s unveiling, Bush remarked that he suspected there would be a good-sized crowd in attendance once word spread of his hanging.

The president’s off-the-cuff remark was characteristically Bush, Anderson said. Even as an undergraduate, Bush had a rare, personable way about him, Anderson said.

“If you were in conversation with him for a while and then you parted and sat down and reflected on what that experience had been like, I think it very likely that you would feel like a million dollars,” Anderson said. “You would feel as if you were in the company of someone who really valued you as a person and someone who made you feel as if he were going to remember something about you — and he did, even when he was not running for anything. That was just his way.”

Anderson’s relaxed rendering of Bush was in line with his artistic philosophy, which is, as he puts it, for his subjects to be “as relaxed as they dare to be.”

His goal is for the people who know the subject well to be able to identify him or her based on their body language in the portrait, even if a brown paper bag were painted over the subject’s head.

Indeed, even as an undergraduate, Anderson was intrigued by the way character could be represented artistically, often drawing caricatures of his classmates and professors in the margins of his books. As a professional artist, he said he views the personal relationship between himself — the painter — and his subject, as absolutely necessary for a truthful conveyance of character.

The most fulfilling part of any project, Anderson said, comes when the painting ceases to be just marks on the canvas and, all of a sudden, as if the sitter heaves a sigh, the painting comes to life.

A trial run, an official painting

In 2002, since he knew the Yale Club of New York would at some point commission a painting of Bush, Anderson contacted the club and threw his name into the ring for the job. He wrote that he was a portrait painter, a Yale alum and a former classmate of the then-president and would be honored to paint Bush. He also sent in his portfolio, which the former president perused.

Two weeks later, Anderson received a call on his cell phone from Air Force One.

“I was looking through this batch of artists. I saw your work and thought this looks great, then I saw your name,” Anderson recalled Bush saying in a 2003 New York Times article.

Yet despite having painted the president successfully once, Anderson said he never took for granted that he would be asked to do one of the official portraits, though he and the president had joked about the Yale club portrait being a trial run for something else. But after viewing the Gallery of Presidents with the former president in the beginning of 2008, Anderson said, it was clear he would be asked to do an official portrait.

“Walking into that gallery, you realized that each of those paintings represents a relationship between a president and a painter,” he said.

He painted the second portrait between September and December of 2008, basing it on photographs of the president he took in the living room of Camp David in April of that year.

And although Bush had less than a month left in office at the time of the unveiling, even his portrait could not escape the partisanship of Washington.

At a time when ills plague the country, Vermont Sen. Bernie Sanders wrote a complaint to the gallery’s director, Martin Sullivan, that took issue with the wall text hung beside it.

The text states the “attacks on September 11, 2001, that led to wars in Afghanistan and Iraq” marked the Bush administration’s tenure. The museum is preparing to change the text, according to a gallery spokesperson. Nonetheless — the controversy notwithstanding — Anderson’s painting of the 43rd president has been a significant boon to his career as an artist.

Path to the portrait

Anderson’s transition from the Yale club portrait to the gallery was smooth, but the path it took him to get there was decidedly not.

Unsure of what career to pursue following graduation, Anderson enlisted in the Navy’s Officer Training School. While he thought about going into education to avoid the draft, he had second thoughts. After four months of training, Anderson was sent to Vietnam, and it was during his six-month stint as part of a support group that he became more introspective and found his calling, he said.

Thus, when an opportunity to go to art school for a semester arose, he jumped at the chance to leave the Navy.

It is to the Navy, he said, that he owes his painting career. In a way, the experience in Vietnam gave him the courage to embark on the unconventional career path he did.

These days, Anderson primarily paints prominent individuals, such as senators and governors. Throughout his career, he has had a number of bizarre encounters with prospective clients.

A particularly memorable episode involved an elderly couple who lived in a Victorian apartment. Anderson, in his final year of art school, was told that they wanted a portrait painted of their daughter, whom they had lost in a fire.

When he arrived at the apartment, Anderson discovered that the daughter was, in reality, a doll that the couple had “adopted” and outfitted with a lengthy wig made from human hair. Though he did sit with the couple for about an hour, perusing photo album after photo album of the couple with their doll, Anderson said that he made sure to keep an eye on the door in case it was necessary to make a hasty exit.

In the end, however, the couple opted not to have the portrait done, since they could not find a photograph that did their “daughter” justice. The experience represents the personal nature of portraiture that attracts him to the discipline, Anderson said.

Realizing he had been remiss in his donations to Yale, Anderson contacted the University’s development office and volunteered to paint the portrait of University President Richard Levin as a donation.

And it is likely he can thank Bush, twice, for his next job.