Ammi Phillips had an unusually long artistic career, painting hundreds of sitters for more than half a century. One aspect of his enduring success was the artist's ability to adapt and perfectly reflect the aesthetic of each era during which he worked. From his earliest—and only known—advertisements published in 1809 and 1810, we know that the artist was already painting in Massachusetts, and that he promised to portray sitters in the prevailing fashion of the day. For many years this led scholars to believe that several artists were responsible for the bodies of work we now understand to have been painted by Phillips during different periods of activity.

This portrait, once identified as Charles D'Emery, is a transitional work between the dreamy and luminous visions of 1812–1819 and the increasing realism and deepening palette of the 1820s, and still exhibits the coarse-woven linen and lean paint of the earlier period. Phillips included the convention of a red curtain, perhaps influenced by the work of academic painter Ezra Ames, whose portraits he undoubtedly saw hanging in the same fine homes along the Hudson where he himself was receiving commissions.

Stacy C. Hollander, "Young Man and Red Drapery," exhibition label for Recent Gifts. Stacy C. Hollander, curator. New York: American Folk Art Museum, 2013.