Fandom as an interpretive community is the frontier for rich insights into the multi-layered interactions and practices between individual users, communities, and intelligent machines. To understand the challenges and opportunities Artificial Intelligence (AI) presents to contemporary media and culture, we discuss how fans engage with AI, as fandom provides meaningful insights into interactions between individual technology users, the collective, and machines. We propose rethinking participatory culture as human-community-machine interactions (HCMI) to understand the wider implications of AI to society and culture. We outline three emerging phenomena and potential consequences of fans’ engagement with AI: (1) fan labour made (un)easy, (2) parasocial interactions (un)familiarised, and (3) realities (un)settled. Our conceptualisation transcends existing computer science research, which assumes technology users as isolated individuals and also fan studies, which largely focus on text-audience relationships and tend to take digital technologies for granted as the preconditions of fans’ creative and playful practices.