This thesis regards cognitive film theory and its application to the character structures of heroes and villains in various Hollywood film productions. The selected material for the analysis ranges widely from cult-classic to bestseller, implying a recontextualization of widely popular and critically acclaimed structures within a popular mass-appeal context. Cognitive film theory deals with providing a framework for understanding characters in light of the emotional responses of the audience. Applying the work of Murray Smith, among others, to a variety of films, the thesis investigates emotional responses to relationships between heroes and villains that are presented as morally ambiguous. Smith’s “structure of sympathy” is an approach that deals with terms, which require the application of tangible empiric data in order to discern how and if sympathy is prevalent for a certain character. Moreover, the cultural frame of American society, pertaining to news through social media as well as the ambiguity of the events regarding WikiLeaks and whistleblowers, is applied to the context of the films as a method of analyzing the relevance of ambiguity as a theme that regards truth and morality within characters. The prevalence of superhero films in the 21st century is extremely relevant for this topic, as it deals with reflections of morality. In recent years a trend has been developing, which deals with superheroes from an ambiguous standpoint in terms of morality by using classical cult-film structures. Older films, as well as the newest editions to the Marvel and Star Wars franchises exhibit clear traits of ambiguity within their constructions of hero and villain, and this is dealt with through analysis of the individual characters and their own exhibition of emotive behavior. The inherent discussion of moral and ideological truth and the definitive good is of extreme popularity in current superhero Blockbuster releases and, therefore, the thesis contains a thorough analysis of emotional responses to ambiguous relationships between hero and villain type characters. The dualistic nature, pertaining to the progressive and aristocratic elements of the various narratives and their character structures, exhibits a set of traits from a wide variety of paradigms that, through the opposition and conflict of the different characters, constitutes a profound reflection and a wish-fulfillment of American cinema that searches for betterment through the opposition and conflict of characters.