This examination of the critical writings of Dionysius of Halicarnassus hopes to suggest two main things: First, recent arguments about the irrelevance of classical rhetoric to postmodern rhetorical criticism-conceived as a general hermeneutic of “rhetoricality”, not only render the notion of “rhetorical criticism” itself increasingly problematic, but also tend to presuppose a simplified (and basically neo-Aristotelian) image of “classical rhetoric” that is unsustainable. Second an more importantly, even as we recognise that ancient rhetoric was oriented toward a discursive realm rather different from that of postmodernity, and without advocating a simplistic “return to Dyonisius”, nevertheless it may be argued that Dyonisius still embodies a general paradigm of “rhetorical criticism” that merits our consideration.