The purpose of this paper is to compare the transformations of the character of Don Quijote in the famous Spanish novel Don Quijote de la Mancha by Miguel Cervantes and of the character of Ernesto Guevara in the movie Los Diarios de Motocicleta (2004), the Motorcycle Diaries, by Walter Salles. Both stories demonstrate the transformations of privileged men, and therefore it is important to analyze them through a Marxist perspective, to better understand how the concepts of superstructure and how David Little’s explanation of false consciousness affected them. A Marxist analysis is necessary to understand that both men were able to live without the oppressive imposition of a class-based society and its subsequent social restrictions. Don Quijote comes from a privileged family and due to his madness, he aspires to embody the ideal knight-errant. However, due to his “locura” and his lack of social awareness, he is not able to identify how he can help people, and instead only strives to personify his idealized perception of a knight-errant. Ernesto Guevara also comes from a privileged family, but instead creates authentic relationships to better understand people’s oppression. Ultimately, Ernesto Guevara transforms into a relatable and empowering leader who fights alongside the people, while Don Quijote is trapped within his idea of the caricature of a knight-errant. This comparison highlights the reality that Ernesto Guevara’s motivations are authentic and help him to develop meaningful relationships with oppressed people.