How central were psychological features deriving from our visual systems to the early evolution of human visual culture? Art making emerged deep in our evolutionary history, with the earliest art appearing over 100,000 years ago as geometric patterns etched on fragments of ochre and shell, and figurative representations of prey animals flourishing in the Upper Palaeolithic (c. 40,000 – 15,000 years ago). The latter reflects a complex visual process; the ability to represent something that exists in the real world as a flat, two-dimensional image. In this presentation, I argue that pareidolia – the psychological phenomenon of seeing meaningful forms in random patterns, such as perceiving faces in clouds – was a fundamental process that facilitated the emergence of figurative representation. The influence of pareidolia has often been anecdotally observed in Upper Palaeolithic art examples, particularly cave art where the topographic features of cave wall were incorporated into animal depictions. Using novel virtual reality (VR) light simulations, I tested three hypotheses relating to pareidolia in the caves of Upper Palaeolithic cave art in the caves of Las Monedas and La Pasiega (Cantabria, Spain). To evaluate this further, I also developed an interdisciplinary VR eye-tracking experiment, where participants were immersed in virtual caves based on the cave of El Castillo (Cantabria, Spain). Together, these case studies suggest that pareidolia was an intrinsic part of artist-cave interactions (‘conversations’) that influenced the form and placement of figurative depictions in the cave. This has broader implications for conceiving of the role of visual psychological phenomena in the emergence and development of figurative art in the Palaeolithic.