Gregory was the first monk to be pope; proverbially, he would have preferred to have remained a monk; the audience he addressed was almost always made up of monks. However, no sustained attempt has been made to establish the contexts for Gregory as a monastic writer. The thesis represents an initial attempt to do so, and in particular, to question the image of Gregory as a monk unable to cope with the assumption of episcopal power. The sources principally chosen for study are as follows: Augustine's Praeceptum; Cassian's Institutes and Conferences; the writings of the early Lerins circle; the Sermons and Rules of Caesarius of Aries; the Rule of St. Benedict, together with the Rules of the Master and Eugippius of Lucullanum. The thesis has been structured as a series of comparisons between these texts, and the situations in which they were produced, with Gregory's writings and his situation in late sixth century Rome. Gregory's ecclesial and eschatalogical perspectives, to which he adhered before papal election, are seen to set him apart from earlier monastic writers, and into confrontation with contemporary ascetics and clerics, the Roman clerical establishment in particular. These aspects of Gregory's thought are related to his rhetorical performance, and the voice he develops is compared to those of earlier ascetics. It is argued that the central concern of the texts considered is that of language: western ascetic projects are seen to focus on holiness of rhetoric, especially in the sixth century. In choosing to speak and write primarily as an exegete, Gregory signalled that he did not wish to contribute to the Gaulish or Italian monastic cultures developing around written Rules. He was concerned instead to articulate a personal holy authority.