This study considers Thomas Hoccleve’s role, throughout his works, as a “religious” writer: as an individual who engages seriously with the dynamics of heresy and ecclesiastical reform, who contributes to traditions of vernacular devotional writing, and who raises the question of how Christianity manifests on personal as well as political levels – and in environments that are at once London-based, national, and international. The chapters focus, respectively, on the role of reading and moralization in the Series; the language of “vice and virtue” in the Epistle of Cupid; the moral version of Chaucer introduced in the Regiment of Princes; the construction of the Hoccleve persona in the Regiment; and the representation of the Eucharist throughout Hoccleve’s works. One main focus of the study is Hoccleve’s mediating influence in presenting a moral version of Chaucer in his Regiment. This study argues that Hoccleve’s Chaucer is not a pre-established artifact, but rather a Hocclevian invention, and it indicates the transnational literary, political, and religious contexts that align in Hoccleve’s presentation of his poetic predecessor. Rather than posit the Hoccleve-Chaucer relationship as one of Oedipal anxiety, as other critics have done, this study indicates the way in which Hoccleve’s Chaucer evolves in response to poetic anxiety not towards Chaucer himself, but rather towards an increasingly restrictive intellectual and ecclesiastical climate. This thesis contributes to the recently revitalized critical dialogue surrounding the role and function of fifteenth-century English literature, and the effect on poetry of heresy, the church’s response to heresy, and ecclesiastical reform both in England and in Europe. It also advances critical narratives regarding Hoccleve’s response to contemporary French poetry; the role of confession, sacramental discourse, and devotional images in Hoccleve’s work; and Hoccleve’s impact on literary tradition.