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—together with a number of friends—also 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.