Gilbert Stuart; Portrait of James Madison; ca. 1805-1807; oil on canvas; 48 1/2 in. x 39 3/4 in. (123.19 cm x 100.97 cm); Gilbert Stuart started his portraits of Jefferson and Madison while living in Washington; D.C. As he anticipated creating copies; he began by painting studies of their faces; which he retained. He then used those life studies to paint portraits in oil. Stuart completed these pendant paintings in Boston; having moved there in the summer of 1805 at the suggestion of former Massachusetts senator Jonathan Mason; who promised to introduce him to prospective clients. Stuart's mother and sister鈥攖ogether with a number of friends鈥攁lso lived in Boston. Though he had led a peripatetic life as an artist; living in Scotland; London; Dublin; New York; Philadelphia; and Washington; Stuart would make Boston his final home. A year after this painting's completion; Madison was elected the fourth President of the United States.