Rui de Oliveiras work is one of the most important collection of illustrations in the Latin America. This research proposes an observation on Rui de Oliveiras work, specifically his black and white illustrations. With a special attention to the works elements that reminisce to the expressionist movies influences, which, in turn, inherit aspects from the theatre and its narrative techniques. The research carefully observes the construction of the expressionist drama by its main representatives in the movies. In the end, this work will establish the narrow relationship between specific works by Oliveira and important selected pieces from expressionist films, through a careful visual analysis of their formal elements.