This chapter considers Dionysius’ evaluation of Demosthenes, the Attic orator whom Dionysius considers the best and most worthy of imitation for his own and future students of rhetorical composition. Dionysius views Demosthenes’ artistry in both a literary mode – in regard to Demosthenes’ literary predecessors and contemporaries – and a political mode – as a means of aiding the attempt of the Augustan regime to refashion the recently secured Roman empire on the basis of a renewed commitment to political, moral, and aesthetic virtues. The chapter considers the background, terms, and methods of Dionysius’ rhetorical criticism: his tripartite scheme of classifying styles and writers; his manner of connecting style with subject matter and occasion; his concern for aesthetic and musical effects; and his attempt to join Demosthenes’ pursuit of political victory with his achievement of permanent literary fame.