This article discusses Chaucer’s perspective on the ideological structures that inform the writing of literary history. In the first verses of the Franklin’s Tale , Chaucer first engenders and then deconstructs an – implicit – teleological narrative of literary history that links questions of genre, orality and history only to deconstruct, in almost the same breath, that very narrative by poetic means. Chaucer’s act of historical deconstruction is compared with the self-conscious strategies of raising questions of literary history as they are already to be found in the type of early Middle English romance he parodies in Sir Thopas . As this article argues, it is through this form of poetic meditation on the problems of literary history that Chaucer establishes a sense of his own modernity.