My practice explores the collaboration of machine learning and the artist to facilitate creativity. The methodology is grounded and engaged with transitional liminal sites found at the fringes of urban habitation. These unadorned landscapes are often harsh and confronting. My agenda is to apply an artistic lens of technology, narrative and symbolism to reveal landscapes that are vital expressions of creative engagement. I incorporate into my practice a machine learning framework termed generative adversarial network (GAN) where two neural networks contest against the other to generate new, synthetic instances of images and videos, challenging my own bias. Interlinked with my practice of erasure and overwriting, the generation of images within these evolving landscapes mirror memory and forgetting. The process of painting adds another layer offering new possibilities. This back-and-forth process using GANs and my own datasets, generates, discriminates, classifies and prunes the visual data mirroring the overwriting of liminal spaces. This loop persists until a lost or forgotten truth has been reconstructed. The merging of artist and machine, questions if the machine still bends to the will of the artist or does it replace the artist all together or is it a symbiotic process.