This presentation explores the performance of John Cage’s Solo for Sliding Trombone using artificial intelligence (AI) generative tools within the Somax2 environment. By integrating AI agents as virtual performers and employing techniques like “coloring the silence” and “expansions,” the project investigates the interplay between human interpretation, AI-assisted performance, and Cage’s concepts of silence, indeterminacy and unintentionality. The research highlights how AI can recontextualize musical relationships, creating “listening topologies” that transcend traditional linear structures. This approach, termed “playing with music,” challenges conventional performance practices while raising crucial questions about copyright, authorship, and the ethical implications of AI in musical creation.