This chapter outlines a profile of Cicero as a literary historian, starting from the idea that his interest in the historical development of literature relates to a broader and more comprehensive interest in history and historiography. The analysis of some digressions about literary history in the dialogues of the fifties (De oratore and De legibus) and forties (Brutus and Tusculanae disputationes) shows that Cicero is interested in placing literary figures on a timeline according to a chronology that he constructs on the basis of synchronisms and other chronological schemes. His method is influenced by contemporary intellectual debates, in which he engages, that led to the production of antiquarian and chronographic works. Therefore, in addition to discussing Cicero’s literary history in light of his intellectual and historiographical interests, this chapter shows how the literary-historical dimension of his oeuvre attests to a lively contemporary context in which various forms of historical knowledge and writing flourished.