This research seeks to answer a question—is it possible to change the overall “image” of a city through changes to individual parts of the cityscape? Based on the approach of urban theorist Kevin Lynch the city of Berlin is analyzed through Lynch’s five elements: paths, edges, districts, nodes, and landmarks. Within Berlin, the Unter den Linden, Berlin Wall, Museum Island, Alexanderplatz, and Brandenburg Gate are analyzed through this lens. The time period from 1989-2015 provides a strong example of a case where a city has been able to reinvent its image. This research utilizes historical images and written accounts of the city of Berlin to track changes to the city’s overall “image.” These accounts and images are then contrasted with those of a visit conducted in June of 2015. Ultimately, much is revealed about Berlin through this analysis of its urban landscape. During the 1990s, many sites across the city were re-designed through high-profile international design competitions that show the global interest in rebuilding Berlin after the fall of the Berlin Wall in 1989. A return to pre-20th century architecture, through rebuilding and restoration, is one significant outcome of this process. The struggle of Berlin, and Germany, to come to terms with the history of former Communist East German is another. This research finally reveals that even after almost 30 years of being a reunified city, Berlin has yet to fully understand its Communist history to the same degree it grasps its Nazi past in the cityscape.