Unexpected Connections: Reimagining the Nineteenth Century through Generative Art is an interactive, generative artwork that offers new modes of archival exploration, discovery and expression using digitised cultural heritage objects. It combines the allure of serendipity with the storytelling potential of palimpsests in order to probe what biography might mean in the digital age. Based upon Mitchell Whitelaw’s interactive work Succession: digital fossils for an industrial age, Unexpected Connections was developed as a tool to explore the inter-crossings of people, places, communication forms, technologies and practices that shaped nineteenth-century knowledge networks. The focal point is the nineteenth-century polymath William Colenso (1811–1899) and his contemporaries. The goal of the project is to simulate an archaeology of knowledge, evoking the geology if not palaeontology of the archival research enterprise, affording opportunities to turn chance encounters into unexpected connections and to rethink digital biography as a complex system of meshworks, lifegrids and life geographies. The article opens with a brief overview of the exhibition context which framed the development of this particular online platform and discusses the various critical, technical and artistic affordances, challenges and futures. It closes with a meditation on the role of such interventions in rethinking collections and their use.