This paper explores how planning, politics and architecture work together to socially produce new vertical cityscapes. Our contention is that the inception and development of high‐rises are interlocked into the narrations of cities, reflecting cultural values and social cleavages, political interests and planning agendas, symbolic connotations and everyday life experiences. By using a mixed‐method approach, which includes the analysis of official documents and interviews with decisionmakers, planners and observers, we examine two trajectories of tall‐building development at opposite ends of Jerusalem. In Israeli West Jerusalem, the development of high‐rises is part of a neo‐liberal growth package that seeks to stimulate economic activity, rebrand the city and increase the city's competiveness at national and global scales while evading highly contentious religious‐cultural cleavages. At the other end of the city, the construction of tall buildings in grey spaces symbolically represents a Palestinian revolt against Israeli restrictive planning and development policies, but also addresses day‐to‐day needs and changing preferences of the Palestinian population. Our analysis uses verticality as a representation of social relations demonstrating manipulations of power and legitimacy. In Jerusalem, planning and development of ordinary high‐rises next to recently completed icons, the Bridge of Strings and the Separation Wall, epitomises a dialogue that unmistakably promotes political agendas and produces symbolic meanings. This dialogue can either support the original values and aims of urban icons or challenge them.