Washington suffered from problems with his teeth throughout his life. He lost his first adult tooth when he was twenty-two and had only one left by the time he became President. John Adams claims he lost them because he used them to crack Brazil nuts but modern historians suggest the mercury oxide, which he was given to treat illnesses such as smallpox and malaria, probably contributed to the loss.

He had several sets of false teeth made, four of them by a dentist named John Greenwood. Contrary to popular belief, none of the sets were made from wood. The set made when he became President was carved from hippopotamus and elephant ivory, held together with gold springs. Dental problems left Washington in constant pain, for which he took laudanum. This distress may be apparent in many of the portraits painted while he was still in office, including the one still used on the $1 bill.

The most famous story about Washington's childhood is that he chopped down his father's favorite cherry tree and admitted the deed when questioned: "I can't tell a lie, Pa." The anecdote was first reported by biographer Parson Weems, who after Washington's death interviewed people who knew him as a child over a half-century earlier. The Weems text was very widely reprinted throughout the 19th century, for example in McGuffey Readers.

Adults wanted children to learn moral lessons from history, especially as taught by example from the lives of great national heroes like Washington. After 1890 however, historians insisted on scientific research methods to validate every statement, and there was no documentation for this anecdote apart from Weems' report that he learned it in an interview with an old person. Joseph Rodman in 1904 noted that Weems plagiarized other Washington tales from published fiction set in England, but no one has found an alternative source for the cherry tree story.