This chapter traces the evolution of “soft machines” and inflatable robotics in the work of artist Chico MacMurtrie/Amorphic Robot Works (ARW). These kinetic machines, which take various forms and scales, explore the underlying essence of movement and transformation in organic and non-organic bodies. The artist recounts his creative journey as well as the technological and material aspects that enable the soft machines to change shape in relation to internal air pressure acting on multiple inflatable tubes, behaving like both muscles and bones. Early performances involving latex skins led to inflatable sculptures powered by inflatable “muscles.” More recent sculptures are conceived as a modular or “molecular” system, comprising webs of interconnected, inflatable members with hundreds of operable joints. The process of constant reinvention and refinement is reflected in the increasing sophistication of the couplings of the inflatable members and of light-weight, minimal-control systems. Interaction between machines and humans has been an ongoing pursuit of the soft machines, which are increasingly designed to interact with each other on the basis of air exchange. Ultimately the goal is to imbue the machines with a capacity for supple gesture and expression.