Although recent commentators have attended to dramatic and ironic aspects of Plato’s Republic, a more sustained examination of the relation between irony and the exchanges of Socrates and Glaucon is required because a crucial purpose and presentation of the irony have largely gone unnoticed. This paper argues that Socratesemploys irony in part to parody Glaucon’s extremism and that he does so to exhort Glaucon to think critically. First, it examines how Socrates uses the term makaria (blessedness) primarily ironically and pedagogically. Then, a possible reason for this use of makaria is advanced: aspects of Kallipolis are a parody of Glaucon and that the parody aims to instruct Glaucon intellectually. This paper hopes to show that such a reading deserves further articulation and examination.