This paper investigates how Gregory of Nazianzus imitates and responds to the Greek literary tradition in the autobiographical poem ‘On his own affairs’ (2.1.1). Through six case studies, it contributes to the ongoing re-evaluation of Gregory’s literary merit. With learning, wit, subtle humour and faith, Gregory adapts and reinvents earlier poetry to express Christian themes. Imitation is at the heart of his poetic technique, but his imitations are never straight-forward. They include imitating both Homer and other poets’ imitations of Homer, learned word-play and combining references to non-Christian literature and the Septuagint. Gregory’s references add nuance to ‘On his own affairs’ and give pleasure to readers trained to judge poetry by comparing it to earlier poetry, especially the Homeric epics. They also demonstrate the breadth of his scholarship, which extends to Homeric variants, Platonic epigrams and the entirety of the New Testament and Septuagint. Above all, Gregory insists that he is a rightful participant in a living poetic tradition. He writes Greek poetry for the fourth century AD, just as Oppian did in the second century and Apollonius and Callimachus did in the Hellenistic period.