Gilbert Stuart American, 1755 - 1828 James Madison, c. 1821 oil on wood, 65.3 x 54.3 cm (25 11/16 x 21 3/8 in.) Ailsa Mellon Bruce Fund
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.