Abstract This paper considers the kinds of AI systems we want involved in art and art practice. We explore this relationship from three perspectives: as artists interested in expanding and developing our own creative practice; as AI researchers interested in building new AI systems that contribute to the understanding and development of art and art practice; and as audience members interested in experiencing art. We examine the nature of both art practice and experiencing art to ask how AI can contribute. To do so, we review the history of work in intelligent agents which broadly speaking sits in two camps: autonomous agents (systems that can exhibit intelligent behaviour independently) in one, and multi-agent systems (systems which interact with other systems in communities of agents) in the other. In this context we consider the nature of the relationship between AI and Art and introduce two opposing concepts: that of “Heroic AI”, to describe the situation where the software takes on the role of the lone creative hero and “Collaborative AI” where the system supports, challenges and provokes the creative activity of humans. We then set out what we believe are the main challenges for AI research in understanding its potential relationship to art and art practice.