At 78, New York artist Raymond Kinstler has probably painted more politicians than any other living portraitist. He counts five presidents, some 50 Cabinet secretaries and at least a dozen Congressmen among his “victims.”

So it’s no surprise that a few years ago when the Senate went looking for an artist to memorialize former Senate Majority Leader Bob Dole (R-Kan.) on canvas, Kinstler — who had painted Dole’s wife, Elizabeth, on three previous occasions — would be a near shoo-in for the job.

Kinstler, who got his start illustrating “cowboys and cleavage” for pulp magazines, said he still experienced a distinct thrill from being selected to paint a Member of Congress for enshrinement in the Capitol: “It’s like an actor who wants to do comedy and tragedy being asked, ‘How’d you like to do Hamlet? How’d you like to do burlesque?’”

While the process of painting for Congress can be rewarding, it can also be daunting. Ideological, bureaucratic and institutional constraints and even stylistic limitations can combine to make a concerted challenge for would-be political portraitists.

“In the case of the government,” Kinstler said, portraits are “more formal … and a little more impersonal. In Washington, it goes through a committee. Everything is done through a secretary. You don’t get that individuality.”

Put Out More Flags

A first glance, the political portrait may seem a rather straightforward affair. Dark suit, Old Glory, a little Congressional architecture or interior in the background, and you’re good to go.

To mix it up a bit, some painters turn to a politician’s ideology or legislative accomplishments to provide visual variation to the standard patriotic props.

Look closely at ex-Speaker Newt Gingrich’s (R-Ga.) official portrait in the Speaker’s Lobby, said its painter, Thomas Nash, and you’ll see an alignment based on the S curve, which charts the evolution of technological change, and which Gingrich wrote about in his paper, “The Age of Transitions.” More obviously, Gingrich is holding a copy of the “Contract with America” and sports a Habitat for Humanity pin on his lapel.

“I’m always looking for ways to imbue the painting with a little more meaning,” Nash said.

The inherently political, and often controversial, nature of Members of Congress also presents artists with added considerations.

While most artists interviewed said that political compatibility is hardly a prerequisite to accepting a commission — “When I’m not near the girl I love, I love the girl I’m near,” the Republican Kinstler quipped — others said the Member’s record played some role in their decision to take on a project.

“In a way, anything I paint or promote, it’s against one’s interest to advertise, promote or join in with any kind of idea one doesn’t agree with,” said Maine artist Alan Magee, who recently wrapped up work on a portrait of former Senate Majority Leader George Mitchell (D-Maine). He said he admired the work Mitchell did on the Northern Ireland peace process and the clean air bill, which made him “one of the few politicians I would have considered painting.”

Mitchell, for his part, said that the quality of the artist and the home-state connection, rather than Magee’s politics, were central to his decision. “I didn’t know his political affiliation when I chose him,” said Mitchell. “In my last visit to his home last fall I got a clue of it. He had a Kerry sign on his lawn.”

Other artists said that politicians and compatible portraitists tended to have a way of finding each other.

“It’s self-selection,” said Nash. “If we didn’t have any chemistry, they wouldn’t chose me.”

That certainly wasn’t a problem for Nash, a longtime fan of Gingrich’s who had observed the then-Congressman at a number of town hall meetings during the 1990s and had come to feel “that I understood him. I recognized that there was a big gulf between what he was really like and in the national media, the impression that was conveyed. Whoever painted him [should be] someone who could do him justice. … And I let him know that.”

Making the Market

Breaking into the Congressional portraiture market can be a tricky proposition for first-timers.

Both the Senate and the House keep files of potential artists on hand, and personal connections and “word of mouth” are key to many artists’ selections, said South Carolina portraitist Michael Del Priore.

After Del Priore painted then-Sen. Strom Thurmond (R-S.C.) for the South Carolina state Capitol, Thurmond recommended him to Rep. Henry Hyde (R-Ill.), who had Del Priore paint his committee chairman portraits for both the Judiciary and International Relations panels. “If they stay in long enough, they hire the same guy back. Sometimes I’ll do the same person two or three times,” said Del Priore, noting that he also painted the late Rep. Bob Stump (R-Ariz.) twice.

For Nash, who had never painted for the Capitol before, securing the Gingrich commission meant personally lobbying the ex-Speaker’s office. (In the 1990s, Nash had suggested painting the then-Congressman, but was told by Gingrich’s staff that “he’s not really a portrait kind of guy.”)

The process tends to take longer for Congressional subjects, several artists said.

Not only does the lengthy approval process required in the Senate tend to slow things down, but studio time with high-profile political figures can also be elusive.

Then there’s the issue of Member involvement. Some, including Mitchell, are intensely involved in the process, said Senate Curator Diane Skvarla. During the selection process, Mitchell personally interviewed the three finalists selected by a Senate advisory panel, and even offered Magee suggestions about his favorite Capitol portraiture, including Aaron Shikler’s strikingly modern, highly realistic rendering of the late Sen. Mike Mansfield (D-Mont.). “It was important to me to see … if he was really engaged,” Magee said.

Other Members may be less involved due to scheduling overload and time conflicts. Kinstler, for instance, first received his contract to paint Dole in 2001, but he is still awaiting a follow-up sitting, and the work’s completion date is now not expected until 2006.

“I think a lot of them think, ‘Why can’t they take a video and a photograph?’” said Skvarla. (Photographs are used during the process, but at least one sitting is usually desirable, and for some artists, like Kinstler, it’s non-negotiable.) To save time, Del Priore said he’ll often set “up mannequins and put a flag behind them.” For more rotund subjects, “I just add a pillow.”

Despite such limitations, Congressional portraiture has its advantages for artists, according to Del Priore. “The one great thing about that avenue is that they have an unveiling built into each one of them,” which serves as a form of advertising in itself.

Moreover, due to the headline-making nature of politics, an artist’s work may also pop up on national television from time to time. During President Bill Clinton’s impeachment hearings, which were presided over by then-Judiciary Chairman Hyde, Del Priore’s portrait of the Illinois Congressman got more than its share of airtime.

“Anyone who was shooting the hearings, that portrait was sitting right over the dais,” said Del Priore. “I got more coverage on that painting than any other.”

Of course, Del Priore added, there is a hierarchy to political portraiture, with Members’ portraits serving in part as stepping stones to scoring the biggest prize of them all: the inhabitant of 1600 Pennsylvania Ave.

“All the portrait painters are leading up to the president,” said Del Priore, who is currently in the process of negotiating possible commissions ranging from Speaker Dennis Hastert (R-Ill.) to President Bush. “Everything leads up through Congress, through the Senate, through the House Speaker, and they go all the way to the White House. … You gotta pay your dues.”

Still, even if an artist is never called to limn the leader of the free world, the honor of being selected for a Congressional commission is often enough. While public-sector compensation is not as high as what is paid by some private-sector clients — the Senate and the White House typically pay $35,000 to $40,000 per portrait, said Skvarla — there are obvious psychic rewards to having a work enshrined for posterity in the nation’s seat of power.

“It was kind of a big thing,” said Magee, whose Mitchell portrait is slated for unveiling in May. “It’s going to a place where these things will be looked at.”