Charles Willson Peale fought in the Revolution at Washington's side and became his most employed portrait painter in the 1770s and 1780s, making more than fifty portraits of the general. This portrait, the last that he painted from life, resulted from an unusual series of sittings in 1795, at which several members of the Peale family painted Washington at the same time. The first sitting was shared by Peale and his son Rembrandt Peale. Charles Willson Peale's brother James (1749-1831) and his sons Raphaelle (1774-1825) and Titian (1780-1798) joined the two artists at the second and third sittings; their portraits have not survived. The unusual sittings led to a much-quoted pun by Gilbert Stuart: "I looked in to see how the old gentleman was getting on with the picture, and to my astonishment, I found the general surrounded by the whole family. They were peeling him, sir. As I went away I met Mrs. Washington, 'Madam,' said I, 'the general's in a perilous situation.' 'How, sir?' 'He is beset, madam no less than five upon him at once; one aims at his eye another at his nose another is busy with his hair his mouth is attacked by a fourth and the fifth has him by the button; in short, madam, there are five painters at him, and you who know how much he has suffered when only attended by one, can judge of the horrors of his situation.'"  
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George Washington