In this double-feature talk, Distinguished Professor Kate Crawford and award-winning artist Trevor Paglen offer a critical look at an emerging landscape of artificial intelligence and autonomous infrastructures in everyday life. Confronting some of artificial intelligence’s foundational assumptions, Kate and Trevor address histories of classification and representation from sixteenth century philosophy to contemporary ‘AI gaydar’, to the tortured relationship between cats and computer vision, to the advent of “invisible images,” to the emergence of monsters and haunted landscapes in algorithmic systems. Kate and Trevor take us on a journey through the strange terrain that is contemporary AI, and show us places where art and critical research meet. While there are no easy answers or ‘quick tech fixes’ to the real concerns about bias built into AI systems, Kate and Trevor suggest new ways to reframe the urgent questions facing us as AI takes on a much bigger role in our lives.