Using musical examples, this research examines the function of generative structures in the creation and reception of artistic works and seeks to identify a dynamic principle operating across styles, media, and historical periods. Thus, it examines how formal, material, and ideational, content may afford aesthetic and non-aesthetic generativity. The research also seeks to diminish the role of dichotomous theoretical frameworks by adopting a systemic affordance-based approach that views artistic works as dynamic sets of creative, generative, and autopoietic actions. The thesis argues that aesthetically generative works involve a principle of incompleteness— identifiable in a wide range of traditional and contemporary artistic practices and styles—that mediates rationality, sensibility, and the imagination. Thus, it seeks to identify generative structures and their ecologies, consider the distribution of cognition in respect to cultural artefacts, and to understand the role of informational lacunae in perceptually and cognitively exploring art environments. This thesis modifies and extends James J. Gibson’s concept of directly perceived perceptual affordances with a view to addressing participant interactions with designed artefacts (and events) mediated by cognitive processes. It seeks to understand the role of affordances in structuring art-defined actions and considers the agency of artists in their creative determination. The investigation adopts Roger Seamon’s four-dimensional approach to artistic works, according to which specific aesthetic values (mimetic, formal, expressive, and conceptual) may be differentially foregrounded. Furthermore, it applies Leonard Meyer’s teleology of musical form to questions of agency and discusses Marcel Duchamp’s work in terms of a quasi-musical interplay of perceptual and intellectual form modelled on chess play. Beginning with tonal music, this thesis considers non-tonal and Experimental music, sound art, ‘non-retinal’ visual art, multi-media installations, and algorithmic technological and non-technological approaches to artistic practice. By describing a generative and participatory systemic model, this research seeks to account for the expanded form/content/audience relationships observable in much twenty-first century art.