In this chapter, Davis Schneiderman revisits William Burroughs’ “Playback Trilogy” – The Job, The Electronic Revolution, and The Revised Boy Scout Manual – as a critical lens for understanding the contemporary challenges posed by generative artificial intelligence, misinformation, and deepfake media. Arguing that Burroughs’ theories of language, media manipulation, and technological control anticipate core dynamics of AI’s influence on culture and perception, Schneiderman explores how Burroughs’ experiments with tape recorders and playback foreshadow algorithmic systems that operate with unintended, emergent consequences. Situating Burroughs’ techniques alongside cybernetic theory and the escalating crisis of automated media, the chapter assesses Burroughs not only as a prophetic figure but also as a practical theorist of language systems gone rogue. From deepfakes to AI chatbots inciting violence, Schneiderman demonstrates that Burroughs’ methods – cut-up, disruption, playback – remain urgently instructive for resisting the logic of control in the digital age.