The research analyses the evolution of automatic drawing technology, starting with some singular mechanical experiences, such as the puppets by Pierre and Henry–Louis Jaquet–Droz and Henri Maillardet up to developments in graphic technology for digital drawing, such as the ones by Ivan Sutherland, Timothy Johnson and Nicholas Negroponte. Finally some potentials in the use of intelligent algorithms are described, showing how it is possible to use shape grammar for architecture, as the experiences by Hank Koning and Julie Eizenberg on Frank Lloyd Wright’s Prairie houses demonstrated.