Although Washington posed for Stuart three times, they were far from pleasant experiences for either man. Washington hated to pose for anyone, and moreover, despite the number of Washington heads attributed to Stuart, the man was not Washington's favourite artist - not even close. Washington appears to have been much pained and bored out of his mind at having to sit still for so long, and on top of that, Stuart had a habit of babbling, on and on, in hope of relieving the obvious boredom and exciting from his subject some spark of life which hopefully he might capture in his likeness. Except for one or two rare, fleeting moments, he was never successful on either count. He tried talking of Washington's military triumphs. The general considered Stuart beneath such chit-chat. He tried telling ribald jokes. That brought only a brief smile on one occasion. Finally, on the third try, he was able to engage the first president in talk of farming, though Stuart admits he knew little on the subject himself. Eventually, Washington began to bring friends with him to his sittings with whom to talk. Stuart's best likeness was the result of these times.

From the artist's point of view, Washington was no easy subject. First, there was the difficulty with the infamous false teeth (whatever they might have been made of). They were a real problem in distorting the lower face in Stuart's first effort, called the Vaughan portrait, painted in 1795. Moreover, the moment Washington settled into a pose, a look of such profound apathy settled over his face one might have expected rigor mortis to set in at any time. Also, Stuart records that Washington's facial structure was quite different from any he'd ever painted before. His eyes were set deep into extraordinarily large cranial openings and the bridge of his nose was far wider than normal. However, in all fairness, it would seem the Vaughn portrait was not a bad likeness. Stuart made no less than fifteen copies of it.

The second effort a year later, is now referred to as the Landsdowne portrait (a gift to a prominent British Whig from whom it gets its name). If the false teeth were an annoyance to both men in the first effort, a different, more ill-fitting, set made matters even worse the second time around, contributing further to the overall disaster this portrait seems to have been from the very start. To begin with, it was troubled by the fact that Stuart had first painted in the standing figure of the president using a friend as a model (if Washington was uncomfortable sitting for a portrait, imagine his discomfort in standing for one). However, Stuart's model was a mere five-feet six-inches in height. Washington was a good six-feet three-inches tall. The proportions were all wrong; add to that the fact that the pose was terribly imperious. It's a matter of dispute whether Landsdowne received the original of this dismal failure or whether it's the one hanging today in the White House. In any case, to make matters worse, there were numerous copies made by the artist himself in order to pay off debts (at least five) and many more made by lesser artists eager to cash in on the president's popularity. None of them got any better than the first.

Only at his wife's behest did Washington relent to sit for Stuart again. If the third time's the charm, this one was so endowed. Painted in 1798, the so-called Athenaeum portrait (it eventually came to be owned by the Boston Athenaeum), was blessed first of all by a decent set of false teeth, a congenial setting for both men (Stuart's stone barn studio at Germantown, a suburb of Philadelphia), and the presence of two or three of Washington's close friends with whom he could chat and relax his famous stone-faced countenance. Though by far the best of the three, this one too has a colourful history. Stuart painted the head and a bit of the background first, leaving the rest of the canvas unfinished as a pretext for not delivering it to George and Martha despite numerous attempts on both their parts to get the artist to part with it.

Stuart used copies of this work to top his Landsdowne copies. He kept the portrait until his death, dashing it off reportedly at the rate of one every two hours. He referred to them as "hundred dollar bills." He sold more than seventy of them. Mrs. Washington eventually received one of the copies. After the artist's death, the original was cut down to a fraction of its planned size. This is the noble, unfinished image that, in printed form, today graces school classrooms all over the nation. Not surprisingly, this painting fell prey to forgeries as well. One bootlegged version ended up in China where it was reproduced hundreds of times by hand for export back to the US. One domestic forger was so proud of the copy he'd made, he took it to Stuart's home to show off, thinking the artist would praise him for his effort and talent. Stuart, incensed, threatened to throw the man out a window.