In his Parekbolai on the Odyssey, the twelfth-century polymath Eustathios of Thessalonike often uses the figure of Odysseus as a starting point to meditate upon crucial themes such as the role of poetry, the duties of the exegete and the qualities of the ideal rhetor. The first part of this chapter focuses on one such passage, where Eustathios analyses the famous ‘linguistic stratagem’ concocted by Odysseus to fool Polyphemus. The sophistic subtlety of Odysseus’ plan leads Eustathios to insert a long excursus on schedography, a rhetorical exercise that was increasingly popular in Komnenian Byzantium. As I argue, in Eustathios’ eyes, the Homeric text is nothing more than a sort of schedographic display ante litteram. More interestingly still, this interpretation provides Eustathios with an ideal pretext for a lesson on rhetorical ‘good taste’. The second part of the chapter examines an extract from John Tzetzes’ Histories in which Odysseus and his adventures again feature as a starting point for reflecting upon contemporary schedography. In this section, I show that, despite some similarities with Eustathios’ ideas, Tzetzes takes a more dogmatic position. As a matter of fact, Tzetzes’ careful depiction of Odysseus might even be interpreted as a subtle criticism of Eustathios’ standpoint.