If you look at a dollar bill, you’ll see an image of George Washington which is, while pensive, neither happy nor sad. The same is true for his portrait on the quarter and, really, for almost every other portrait of the first President of the United States and Commander of the Continental Army. The exception: the image above. President Washington is clearly quite upset.

Why? Most likely, he was tired of sitting for portraits all the time.

The above portrait was painted by a man named William Williams (really) who, per his sparse Wikipedia entry, is “widely regarded as the first American portraitist.” Over his career, Williams painted portraits of a number of Founding Fathers including the first three Presidents of the United States. It’s unlikely that George’s sourpuss is the result of a less-than-skilled artist.

Williams, through Virginia Governor Henry Lee (a friend of Washington’s), requested that Washington sit for the painting above. But Washington was not interested in posing. According to Laura Simo, a curator at George Washington’s Mount Vernon Estate Museum and Gardens (via this video from the National Archives), Washington posed for more than a dozen portraits during his eight years in office — each of which required a few hours sitting and, for some, a few return visits for touch-up work and completion. The portrait-painting process — as the subject — was not one Washington enjoyed. In a return letter to Lee, dated July 3, 1792, Washington declined the offer to sit:

[T]o be frank, and I hope you will not be displeased with me for being so, I am so heartily tired of these kinds of people that is now more than two years since I have resolved to sit no more for any of them. [. . .] [B]esides the irksomeness of the sitting and the time I lose by it . . . these productions have in my estimation been made use of as a sort of tax on individuals by being engraved (and that badly) and hawked about or advertised for sale.

In response, to help the President’s concerns, Williams agreed to give the portrait — if he were granted permission to paint it, that is — to the local lodge of the Freemasons, of which Washington was a member (and which would later take his name). Eventually, Washington capitulated — but apparently, he was not too happy about it.

Bonus fact : On April 12, 1945, at around noon, then-President Franklin Delano Roosevelt sat for painter Elizabeth Shoumatoff. During the sitting, while the President ate lunch, he complained of a “terrific pain in the back of [his] neck” and suddenly slumped forward, collapsing. FDR had suffered a stroke and died at 3:35 that afternoon. Shoumatoff never completed the portrait, preferring to leave in unfinished given the circumstances. It can be seen here.

From the Archives: The First Photograph of a Person: It, too, was the result of a slow process.

Related: “FDR’s Unfinished Portrait: A Memoir” by Elizabeth Shoumatoff. Out of print, with some cheap used copies available.