Massively multistable materials, such as crumpled sheets, display strikingly complex sequential responses when driven. These responses arise from their rugged energy landscapes, which emerge due to disorder and frustration. This makes the understanding, characterization and design of the sequential response of multistable materials both a fundamental challenge and a technological opportunity for sequential shape morphing, soft robotics and in-materia computing. In this thesis, we address three interrelated questions at this frontier. First, we explore how richer modes of driving fundamentally reshape material behavior. Second, we investigate the minimal building blocks that generate exotic sequential responses. Third, we develop a scalable driving strategy that utilizes dynamics to write many states in a single drive cycle to unlock the full potential of multistable materials. Together, these contributions advance our understanding of the fundamental physics of frustrated and multistable systems, and build toward a framework for their characterization, control and rational design–paving the way toward programmable and adaptive materials.