This paper builds on the premise that art has a significant role to play in engaging with and exploring new technologies and in contributing to interdisciplinary conversations. Artists have often been pioneers in reflecting upon social and technological transformations by creating work that makes explicit the dangers, but also the exciting possibilities ushered in by innovation. After having, albeit briefly, traced the history of art engagement with technology (computer/net-art, generative art), the paper will focus on AI-art, now defined as GAI-art, to understand whether artificial intelligence is “set to become art’s next medium?” The question was prompted by the sale at Christie’s in October 2018 for $432,500 of a portrait entitled Edmund de Belamy, a work created by an algorithm called Generative Adversarial Network (GAN). The source code used by the Paris based art collective Obvious (borrowed from AI researcher/artist Robbie Barrat) to create the “artwork” triggered a debate as to the authenticity, authorship and ethics of using GAN to produce AI-art. The paper will contribute to such debate by exploring also the implications of systems more sophisticated than GAN – which seem to be able to act as “autonomous artificial artists” and produce new styles of art – and by showcasing the works of some of the most representative machine vision researchers/artists – Anna Ridler and Mario Klingeman, among others. AI artworks raise major philosophical questions, the meaning to be human in a hyper-connected world and the true nature of human creativity. In fact conceptualising AI through the artificial artist’s eye might even challenge our understanding of what it means to be human.