The authors discuss the development of self-organizing artworks. Context Machines are a family of site-specific, conceptual and generative artworks that capture photographic images from their environment in the construction of creative compositions. Resurfacing produces interactive temporal landscapes from images captured over time. Memory Association Machine's free-associative process, modeled after Gabora's theory of creativity, traverses a self-organized map of images collected from the environment. In the Dreaming Machine installations, these free associations are framed as dreams. The self-organizing map is applied to thousands of images in Self-Organized Landscapes—high-resolution collages intended for print reproduction. Context Machines invite us to reconsider what is essentially human and to look at ourselves, and our world, anew.