This dissertation studies a case of Enlightenment art created in feudal conditions of servitude. The Sheremetevs, one of the richest and most powerful families in eighteenth-century Russia, had some of their hundreds of thousands of serfs trained as painters, architects, opera singers, and musicians. Two of these serfs, Ivan and Nikolai Argunov, became successful portraitists who painted a range of sitters from Empresses to fellow serfs. Tensions between social rank and individuality, already a preoccupation for eighteenth-century portrait painters, became particularly pronounced in this situation. While recent scholarship has focused on the Argunovs' cosmopolitan influences, their paintings of fellow serfs and others of low rank are sometimes visually and iconographically distinct from their usual output. This category of portrait, this dissertation argues, should be considered within the context of the other artistic projects of the Sheremetev household. Despite strong Western European influences on the Argunovs, the painters were also exposed to extremely personal and local precedents. These include earlier portraits, garden prints, an atlas project, the Sheremetevs' many collections, and operas staged by the family's renowned serf theater. Working within this visual environment, Ivan and Nikolai Argunov painted their subjects in intricately allusive ways. Their portraits represented and negotiated the complications of serfdom in a setting where unusual social change was possible.