The realization of the Frank Gehry-designed Guggenheim Museum in Bilbao is probably one of the most recurrently narrated success stories regarding the role of contemporary architecture in promoting urban regeneration, economic development and city branding. It is referred to as a model for regeneration by many scholars and, more importantly, it is a ubiquitous narrative among urban decision makers worldwide. Despite the fact that these sorts of branded projects have been changing the landscape in several cities, attention to the decision-making mechanisms and the rationalities implied in such processes is today limited or misinterpreted. In the following paper I present observations about projects for localizing Guggenheim Museum facilities in global and medium-size cities, as well as a set of urban development processes involving spectacular and branded architecture in Abu Dhabi, Paris and New York. The conclusions of the paper are two-fold: referring on the one hand to the international scholarly debate, and on the other to more urgent questions for urban policy makers in contemporary cities. Representing branded and aesthetically striking pieces of architecture as a determinant factor in regeneration does not respond to actual urban processes (in terms of actors’ motivations, public relevance and desirability of effects), but, nonetheless, it has been the means for spreading beliefs and behaviors among decision makers and provided certain actors with seemingly favorable conditions. However, policymakers can critically reinterpret these projects as the exploration of new cultural places, involving a broader set of actors and interests and fostering a more sustainable evolution of urban landscapes.