American painter Gilbert Stuart was one of the masters of 18th century portraiture, best known for his portrayal of George Washington (as seen on the one dollar bill) and other founding fathers. His unique ability to capture likeness and represent the character of the poser set the standard for portraiture.

Gilbert Stuart was born on December 3, 1755, in Saunderstown, Rhode Island, a descendant of Scottish immigrants Gilbert Stuart Sr. and Elizabeth Anthony. After settling in North Kingston, Rhode Island, his father, in partnership with two other local men, built and operated the first waterpower snuff mill in the colonies that manufactured tobacco and dry goods.

When Stuart was seven years of age, the family moved to Newport after selling their interest in the mill. He began his apprenticeship under Italian-trained Scottish artist, Cosmo Alexander. Together, the pair travelled to Scotland in 1770 on a painting tour. Two years later, Alexander unexpectedly died on a stop in Edinburgh, leaving the seventeen-year-old stranded and destitute. A few odd jobs earned him enough money to return home to Newport in 1773. When his father decided to move his family to Nova in 1775, the young artist decided to go out on his own to London, where he eked out a living working as an organist, in between earning scanty commissions as a painter.

Work was meager for a portraitist in times of war; the American Revolution caused prospects to be few and far between. In 1777, Gilbert Stuart reached out to Benjamin West in a letter that earned him an assistant position with the artist for the next six years. That same year, he exhibited a portrait at the annual exhibition of the Royal Academy of Arts in London for the first time. ‘The Skater’ (1782), a portrait of William Grant skating at St. James Park on the Serpentine River, received much acclaim. Getting the break he needed, he quit his job as an assistant and went out on his own once more.

Gilbert Stuart moved to Dublin, Ireland in 1787 trying to escape the financial problems he was having in the U.S., but continued to make bad finanial decisions that forced him to spend some time in a debtor’s prison. He returned to the U.S. several years later and opened up a studio in Philadelphia. Earning the commission to paint George Washington, the newly elected President (1797), would turn out to be his greatest success. This famous painting was almost destroyed in the war of 1812, but was rescued by the First Lady, Dolley Madison.

In 1803, Gilbert Stuart set up shop in the nation’s capital, where he produced more works featuring former Presidents such as Adams, Jefferson, Madison, and Monroe. He painted governors, diplomats, military heroes and other important people. Two years later, he moved to Boston, where he lived out the rest of his years. After suffering a stroke in 1824, paralysis put an end to an unforgettable career. Stuart died on July 9th 1828, at the age of seventy-two. He was buried with many other influential Americans in the Old South Burial Ground in Boston.