Note the quivery lipline.

Have a look at the picture of George Washington on a dollar bill. Note his stiff, unsmiling lips. Doesn’t he look uncomfortable? Well, he was. He had a raging toothache.

The portraitist, Gilbert Stuart, was a charming guy and well known for getting his subjects in a good mood with his lively banter. But Washington turned out to be a tough nut. When he was elected President in 1789, he had just one tooth left in his whole mouth.

Gilbert "Funster" Stuart, Washington's portraitist

According to a fascinating book called The Excruciating History of Dentistry, Washington owned many types of false teeth, including sets made of lead, human teeth, and elephant and walrus tusks. The ones in his mouth in the dollar bill portrait were made of hippopotamus ivory. Not only did they ache, but they made his mouth jut out.

After his last tooth was pulled out, in 1796, Washington was no longer able to anchor his dentures to anything inside his mouth. It was probably impossible to chew anything. The poor man had to keep his lips tightly closed to prevent his dentures from popping out of his mouth.