Walter Benjamin and Rem Koolhaas developed two significant investigations, which explored the culture of Paris and New York through the analysis of their architectural artifacts. Their research projects successfully construct, from a few meaningful components of the built environment, an understanding of the overall city and its society. The objective of this paper is to address the similarities between the research carried out at the Federal University of Rio de Janeiro and the work of these two acclaimed writers. Our group aims to select urban icons, from different moments and areas in Rio de Janeiro, to be studied in order to understand the city evolution in the 20th Century. The distinguished Ministry of Education building is the investigation's prototype, analyzed thorough several 3D models and other digital techniques. We conclude that a thorough study of Benjamin's and Koolhaas'work should be considered a primary support for the interrogation of our own investigation.