William Dunlap’s diary recounts a life spent wandering in pursuit of commissions and sleeping in rented rooms away from home: having traveled continuously for two months, on February 19, 1806, he observed that it was his fortieth birthday and he was away from home. This self-portrait probably comforted his wife, Elizabeth Woolsey, and their children during his journeys along the eastern seaboard while they remained in Perth Amboy, New Jersey. The miniature might have also held personal meaning for Dunlap, whose turned head suggests a degree of self-consciousness about his appearance. As the result of a childhood accident, he was blind in his right eye. In addition to his career as an itinerant artist, Dunlap is known as the first historian of American art. His History of the Rise and Progress of the Arts of Design in the United States (1834) traces the challenges of portrait-making in early America. Following an unsuccessful period of study in London with Benjamin West, Dunlap returned to New York, where he became involved in the theater, first as a playwright and then as a theater manager. In 1805 his company went bankrupt, and Dunlap returned to painting, pursuing miniatures, full-scale portraits, and large history paintings that he exhibited in major eastern cities.