This thesis aims to examine the outlook of writers of contemporary history in England between 1377 and 1422. The chroniclers have traditionally been characterised as writers who, despite some individuality, were spokesmen for establishment views and lesser successors to the chroniclers of the eleventh to thirteenth centuries. In contention with this perception, the thesis approaches the chroniclers through a comparative analysis of their treatment of the Crown and the Church, their construction of communities, their reports of martiality, and their engagement with contemporaneous comment, criticism, and debate to show that their intellectual journeys belie superficially communal attitudes. The premise of this thesis is that the late medieval regular and secular clerks who wrote Latin chronicles in England were engaging in multiple discourses and were responding to contemporary pressures rather than simply continuing existing traditions. The thesis aims to re-examine these texts to offer a new perspective on the intellectual complexities of historical writing during this period. It argues that the chroniclers, despite some superficial similarities in their backgrounds and probable experiences, were highly idiosyncratic. This thesis problematizes terms such as ‘regular chronicler’ or ‘secular chronicler’ which obscure the complex web of experiences that connected various regular and secular chroniclers whilst dividing them from their fellows through their professional and intellectual experiences. It explores key issues such as the chronicler’s social backgrounds, educations, and their engagement with forms of narrative and discourse. The thesis suggests instead that whilst many of the chroniclers were thoroughly involved in their intellectual and textual milieu this produced a plethora of responses from them rather than a single one. The thesis concludes that the chroniclers were far from being the uninspired commentators they have been described as by V. H. Galbraith, John Taylor and Charles Kingsford, and neither were they an elite set of voices as Steven Justice suggested. Instead, it argues, the chroniclers were a set of authors who were in fact actively reflecting on political, social, and intellectual issues. It suggests that first, they were deeply immersed in the culture of the universities, and the Oxford schools in particular. Second, that they did not have a united perspective on the establishment, and that this is demonstrably the case from the study of their depiction of the Crown and Church, how they constructed communities, and how they reported warfare. Third, they were not only engaged in the surrounding textual culture and the debating practices, such as scholastic sermons, which were becoming ever more important, but that they also often shifted their own position and adopted different forms of discourse. This thesis is an addition to the work that has already been done on monastic and clerical intellectual life and culture in the late fourteenth and early fifteenth centuries. It aims to go beyond the existing historiography in presenting a new examination of the chroniclers’s outlooks which demonstrates the complexity and many distinctions that individuated them.