The continuous transformation of the Urban Landscape in the American and European cities has established the foundations for a discourse that moves back and forth in the Atlantic. Through the comparative analysis of urban themes, evidence of the three dimensional urban space is revealed, creating a new kind of relationships; spatial patterns and forms. Two case studies, deceptively different in organization, are chosen to analyze the metropolitan city as the understanding of the entire urban area can never been seen and examined. The street, an arena of social expression operating in multiple scales, becomes the characteristic area. It is not an exterior space formed among building cells, but a space interwoven in the urban fabric. Three-dimensional systems, variations of spaces and other elements, rearrange the Grid of the metropolitan landscape transforming it into a multi-layered organism. This study is a device for questioning different approaches to the same subject opening up an area for further experimentation. It reflects a small part of an evolving dialogue among architects, planners and all who wish to tackle issues relevant to the formation of the Urban Landscape.