During the first two centuries C.E., provincial Greek elites reacted to their new status as denizens of the Roman Empire in part with the literature they produced, often grouped under the heading of the Second Sophistic. The tail end of this period, in which a new dynasty of emperors ruled and underwent a crisis of legitimacy (193-235 C.E.), was markedly different in the identity of the imperial family and as a result the composition of Greek literature. This distinction, however, has not been part of the scholarly approach to the study of this period’s literature, which instead focuses on the traits that it shares with earlier sophistic literature. During this later period, the debate over what constituted proper “Romanness” acquired renewed cultural importance especially because of the Severan imperial family’s outsider status, Syrian and African background, and decree of universal citizenship in 212 C.E. As an intimate of the imperial family and prominent Greek intellectual in Rome, Philostratus witnessed these changes firsthand. By reading the diverse works of Philostratus together, I argue that the corpus reacts to contemporary cultural change by portraying foreign identity as disruptively ambiguous. My analysis illuminates the distinctive features of this period, including the cultural status of Greece and Hellenism, the incorporation of outsiders, and the nature of Roman identity in times of political change, if not outright crisis.