This thesis contributes to the growing body of scholarship surrounding historical and filmic representations of the past. Moreover, it seeks to further the understanding and practical use of this sub-field in history by examining two films: Amistad (1997); and, The Wind That Shakes the Barley (2006). Building on the insistence of scholars such as Robert Rosenstone and Hayden White, this thesis seeks to evaluate historical films on their own terms as representations of the past that must be judged according to their own conventions. Cinema's attraction to historical subjects is not a recent phenomenon. However, the past two decades, have seen a marked increase in the academic critique of 'historical films' - most notably Hollywood features and television documentaries. Moreover, the appetite of the general public for filmic treatment of historical topics continues unabated. While it is agreed that historical film cannot be judged according to the criteria used in accessing traditional modes of historical representation, there is little agreement about what criteria, precisely, should be used in evaluating historical films' historical attributes and implications. This thesis commences with a general theoretical and methodological survey of the literature in this relatively new sub-field. It then analyses the film Amistad and its reception and criticism amongst historical professionals. This analysis, coupled with the findings of the first chapter, forms the basis for an original and independent review of The Wind That Shakes the Barley, a film that has not yet been widely critiqued by historians. The thesis suggests how historical films may be fruitfully evaluated in ways that are sympathetic both to the peculiar exigencies of the medium and the traditional concerns of historical scholarship.