This essay explores the intersections between ancient and modern notions of ecphrasis (defined by Imperial Greek rhetoricians as “a descriptive speech” that “brings the subject shown before the eyes with visual vividness”). After surveying recent comparative literary approaches to ecphrastic “intermediality,” the essay first analyzes theories of ecphrasis in the Progymnasmata. Second, by relating these Imperial Greek rhetorical discussions back to literary and literary critical traditions, the essay posits a closer relationship between ancient and modern ideas of ecphrasis than is often assumed. Third, it surveys “self-standing” ecphrasis in epigrammatic poetry, paying particular attention to epigram’s paragonal pitching of vision against voice (and vice versa). Finally, the Elder Philostratus’ Imagines is introduced as antiquity’s most sophisticated meditation on words and images—at once resonating with earlier literary traditions and anticipating some of the most pressing questions about ecphrasis in contemporary literary critical theory.