| Preview | Description | Notes | Content | Updated by
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 | Robert R. Livingston 1793-1794 Clermont State Historic Site One Mile North Of Tivoli, NY |  Robert R(obert) Livingston (27 November 1746 – 26 February 1813) was an American lawyer, politician, diplomat from New York, and a Founding Father of the United States. He was known as "The Chancellor," after the office he held for 25 years. | Unrated | Anonymous |
 | Portrait Of John Jay 1794 National Gallery of Art Washington, D.C. | John Jay (December 12, 1745 – May 17, 1829) was an American politician, statesman, revolutionary, diplomat, a Founding Father of the United States, and the first Chief Justice of the United States (1789–95). | Unrated | Anonymous |
 | Anna Payne Cutts 1804 The White House Collection Washington, D.C. | Unrated | Anonymous | |
 | James Madison 1804 Colonial Williamsburg Foundation Williamsburg, VA | James Madison, Jr. (March 16, 1751– June 28, 1836) was the fourth President of the United States. He is widely regarded as the “Father of the Constitution” and the author of the Bill of Rights. He has been called the chief architect of the most important political experiment in human history. | Unrated | Anonymous |
 | Jerome Bonaparte 1804 Private Collection Unknown, USA | Jerome-Napoleon Bonaparte, French Prince, King of Westphalia, 1st Prince of Montfort (15 November 1784 – 24 June 1860) was the youngest brother of Napoleon, who made him king of Westphalia (1807–1813). After 1848, when his nephew Louis Napoleon became President of the French Republic, he served in several official roles. | Unrated | Anonymous |
 | John Adams 1826 National Museum of American Art, Smithsonian Institution Washington, D.C. | John Adams (October 30, 1735 – July 4, 1826) was an American statesman, diplomat and political theorist. A leading champion of independence in 1776, he was the second President of the United States (1797–1801). Hailing from New England, Adams, a prominent lawyer and public figure in Boston, was highly educated and represented Enlightenment values... | Unrated | Anonymous |
 | Thomas Jefferson c. 1821 National Gallery of Art Washington, D.C. | Stuart painted the third president from life three times during his administration of 1801 to 1809. This Gibbs-Coolidge rendition was most likely based on other pictures Stuart had painted from life that where either in his possession or accessible to him. | Unrated | Anonymous |
 | James Madison (1) c. 1821 Private Collection Unknown, USA | Stuart first portrayed James Madison when he was Jefferson's secretary of state. The Gibbs-Coolidge likeness may have been painted from life during Madison's two terms as president from 1809 to 1817. The deep green curtain accents the color of Madison's eyes. | Unrated | Anonymous |
 | James Monroe ca. 1820–22 Metropolitan Museum of Art New York, NY | James Monroe (1758–1831) fought in the American Revolution, served in the Virginia legislature, and was elected to the Continental Congress. After acting as both secretary of state and secretary of war during the War of 1812, he became the fifth president of the United States in 1817 and served until 1825. His greatest accomplishments included the... | Unrated | Anonymous |
 | John Quincy Adams 1818 The White House Collection Washington, D.C. | John Quincy Adams (July 11, 1767 – February 23, 1848) was the sixth President of the United States (1825–1829). He was also an American diplomat and served in both the Senate and House of Representatives. | Unrated | Anonymous |
- Gilbert Stuart
