Dozens of presidential portraits hang in the bright halogen wattage of the National Portrait Gallery; 42 grace the White House. Gilbert Stuart set the template when he painted Washington in the rancorous waning years of his presidency. A bust-length version appeared on the $1 bill in 1869 and remains there today, making it the most-reproduced image in history. A full-length version hangs prominently in the East Room of the White House, and every president since John Adams has had to measure himself against the great man’s penetrating gaze.

Other presidential portraits followed the precedent of Stuart’s Washington, standing by a desk strewn with books and papers. In the White House, those of Presidents James Polk, Millard Fillmore, Franklin Pierce, Rutherford Hayes, Benjamin Harrison, George H.W. Bush and George W. Bush are variants of the Washington original.

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A different presidential image, also pioneered by Stuart, had Thomas Jefferson seated at a desk. Knowing that the projection of personality was at the heart of politics, Jefferson wanted to embody “chaste republican character” by being portrayed as a man of the people doing his ordinary daily work. That “Jeffersonian” style was adopted in White House portraits of Presidents John Quincy Adams, John Tyler, Grover Cleveland, Franklin Roosevelt and Richard Nixon.

As one might expect, these portraits tell stories, and not always true ones; spin has always been a part of any presidential legacy. Though the goal of the presidential portrait is commemorative, at a more ambitious level, it is political: to influence and, if possible, control posterity’s judgment of a president.

It’s been this way from the start. In Stuart’s full-length, Washington stands majestically, in a plain black suit by a cluttered desk, dignified and serious, bordering on remote. That hardly described his character. After their first meeting, the startled artist wrote that “all Washington’s features were indicative of the strongest and most ungovernable passion, and had he been born in the forest, he would have been the fiercest man among the savage tribes.” On another occasion, Stuart watched the president “seize a man by the collar and thrust him violently across the room.” Washington’s “ungovernable passions,” as one commentator put it, were well known in 1796. But his lifelong quest was to subdue and redirect that temper, to be known as a leader of prudence and wisdom.

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For his part, the supremely talented Stuart, who was always aware he was working for the political elite, considered it his job to fashion Washington into that prudent and wise leader. He painted more than 100 portraits of Washington, in which he is repeatedly encountered as the Republic’s iconic chief of state. Stuart’s brilliance was not just a matter of artistic technique; it was also an ability — and a willingness — to be political choreographer for the strategic desires of the presidents he served: Washington, Adams, Jefferson, Madison and Monroe. Never did he consider himself an independent political voice.

Washington clearly recognized Stuart’s value in his long-term project of legacy-building. Explaining his logic to a skeptical Lafayette, Washington said that artists and writers “hold the keys of the gate by which Patriots, Sages and Heroes are admitted to immortality;” they are the “doorkeepers to the temple of fame.” And of all the artists and writers shepherding Washington toward that temple, it was Stuart who, better than anyone else, crafted the imposing image that has endured for 220 years.

A number of other presidents have used talented artists to project their public image. Ronald Reagan, in a portrait by Everett Kinstler, radiated his renowned affability. Seated on the Truman balcony of the White House, he is the only president positioned out of doors, smiling so broadly that his teeth show.

But not all official portraitists followed the wishes of presidents, and presidents sometimes sat for painters without complete foreknowledge of what would emerge on the canvas. Theodore Roosevelt originally had himself painted by a Frenchman who, it was said, made the former Rough Rider look like a “Mewing Cat.” Roosevelt had the painting destroyed, and then hired John Singer Sargent — another artist who knew how to amplify a client’s desires — to paint him standing on a staircase, latching one hand onto his hip, flaring his elbow, looking dead ahead and grasping a newel post as if the Earth itself were under his command.

Rarely has an official portraitist had the temerity to paint something that would be an open embarrassment to the sitter. Graham Sutherland’s controversial 1954 portrait of Winston Churchill was merely harsh. But Nelson Shanks’s portrait of Bill Clinton is hostile. Shanks deposited a poison pill into his portrait of Clinton at the National Portrait Gallery: the shadow of Monica Lewinsky’s dress, cast onto a nearby fireplace. Over that fireplace, a portrait of Washington is cropped at the neck, as if the first president would prefer to look away from the unseemliness. Shanks’s goal, we can infer, was to be doorkeeper to the temple of infamy.

He doubled the inappropriateness when he let Clinton review and accept the picture before revealing its humiliating content. Then tripling the stakes, he declared the president “probably the most famous liar of all time.” Though the cost of the Clinton portrait is unknown, Shanks has received as much as $200,000 for a full-length portrait, a lot to be paid for public mortification. Maureen Dowd called it “devilish punking,” which it would be in a political cartoon. But in an official presidential portrait, it registers more like a toxic brew of passive aggression and political opportunism.

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President Obama’s official portrait has yet to be painted. Over the centuries, the acquisition date of a presidential portrait has varied widely (Herbert Hoover’s was painted 23 years after he left office), but more recently it has occurred during the next president’s term, when the sharpest political and personal comparisons can be made. We can speculate on what Obama’s portrait might look like, whether he will be standing or sitting, introspective or gregarious, a doer or a thinker. The format might be traditional or original, the artist African American or not. But whatever the format or whoever the artist, the occasion will be momentous. The portrait will join a presidential cavalcade that includes those who worked for the civil rights that made Obama’s election possible: Lyndon Johnson, Ulysses Grant, John Quincy Adams and Abraham Lincoln. At the same time it will stand as a permanent rebuke to all those who stoked the flames of racism, most egregiously Andrew Johnson, Woodrow Wilson, James Polk and John Tyler.