The development of new shapes in architecture has deeply influenced the current perception of the built environment. The analysis of the processes behind this evolution is, therefore, of great interest. At least two well known factors, influencing this development, may be pointed out: the great improvement of digital tools and the tendency toward building distinctiveness.In particular, the innovation of digital tools such as parametric modeling is resulting in an overall diffusion of complex shapes, and the phenomenon is also evident in a clear expressionistic search for architectural singularity, that some might consider as a negative effect of globalization trends.Though, if we can consider as a positive result the fact that parameterization allows a deeper control over design factors in terms of reference to cultural, historical and physical context, at the same time such control possibilities are sometimes so stark to be even auto-referential, stepping over site-specific parameterization, to create unusual shapes just for the sake of complexity.The ever-growing diffusion of generative design processes is in fact going to transform niche procedures, frequently limited to temporary decontextualized structures, into an architectural complexification as an end in itself.The hypothesis of this paper is to demonstrate that site-specific parametrization can be considered as a tool able to translate intentions into shape; it is necessary, for this aim, the widening of the meaning of the word singularity.