This article presents recent outcomes of the author's research on musical complex adaptive systems (CASs). The first part focuses on the concepts of adaptation and complexity within the framework of CASs and suggests a rigorous placing of the concepts within the musical domain. This analysis involves a distinction of the notions of context and information between the engineering field of information theory and the philosophical one of radical constructivism. I conclude this section by showing that, in this approach, information and context are mutually determining.

Then, I introduce a technique related to the notion of evolvability in biology and genetic algorithms and that has significantly increased the complexity and long-term variety in music systems during autonomous evolutions. This technique distributes adaptation across higher levels and allows the system to reorganize the relationships among its agents and their structure circularly while interpreting and constructing its context.

To conclude, an autonomous live performance piece from 2019–2020, “Constructing Realities (Homage to Heinz von Foerster),” which implements the theories mentioned above, is described, showing DSP processes and techniques that relate to evolvability, autopoiesis, fitness, and complexity through agent-based modeling. This article is accompanied by a companion article discussing the technical aspects of information processing algorithms, which are an essential part for the implementation of music CASs: “Time-Domain Adaptive Algorithms for Low- and High-Level Audio Information Processing.”

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