The famous claim that George Washington sported a set of wooden teeth is little more than a myth, but America’s first president was certainly not a shining example of oral hygiene.

Dental issues plagued Washington for most of his adult life. He began losing teeth as early as his twenties, and was eventually forced to wear several sets of unsightly and painful dentures. Rather than wood, Washington’s many false choppers were made out of varying combinations of rare hippopotamus ivory, human teeth and metal fasteners. He got his first set before the Revolutionary War, and may have also undergone a “tooth transplantation” procedure—perhaps even using teeth purchased from his own slaves—in the mid-1780s with the help of his personal dentist and friend, Jean-Pierre Le Mayeur.

Nevertheless, by the time he was inaugurated as president in 1789, Washington only had a single natural tooth left. He took the oath of office while wearing a special set of dentures made from ivory, brass and gold built for him by dentist John Greenwood. After Washington lost his sole surviving tooth, he gifted it to Greenwood as a keepsake.

Though Washington’s dentures were fashioned by some of the best dentists the late 18th century had to offer, they still left him disfigured and often in pain. Keeping his false teeth looking pearly white was a constant chore, and Washington often shipped them off to Greenwood to keep them in working order. The teeth would easily turn brown without regular care and cleaning, and their occasionally unsightly appearance may have first jumpstarted the rumor that they were made from wood.

Worse still, the dentures caused jaw discomfort and forced the President’s lips to, as he once wrote, “bulge” in an unnatural fashion. This facial disfigurement is particularly apparent in artist Gilbert Stuart’s famous unfinished painting of Washington from 1796—the same portrait that appears on the one-dollar bill.