My talk tracks the routes through which texts and images have moved across the expanse of Eurasia during a period long before the advent of modern media and global capital. In doing so it urges us to attend to those dynamics of circulation that tend to get obscured by an exclusive focus on the dramatic changes brought about by contemporary globalization. What are the processes that unfolded as a result of the long-distance migration of objects and their makers as well as patrons across a vast zone stretching from the Mediterranean across West and Central Asia to the Indian subcontinent? The mobility of literary and pictorial representations across linguistic and cultural borders, I argue, did not lead to a dissolution of differences, but to a dialogical process of negotiation and transformation that unfolded over extended periods of time. Visual encounters involving traditions of Greek and Byzantine Antiquity, Christianity and Islamicate cultures, were enabled by a mix of transregional movements – trade, travel, migration, missionary activities and, not least, conquest. Makers of images in early modern court cultures showed a nuanced awareness of different visualities as well as of shared symbols, and treated the painted page as a zone of contact. My presentation of selected examples from South and West Asia will draw attention to articulations of worldly awareness as well as modes of self-reflection transmitted by pictorial practices as they participated in a dynamic that involved assimilation, reconfiguration, translation, or refusal. Examining such processes sensitizes us to the ways in which cultures across time and space understood borders and problematized them, often playfully. For scholarship today, investigating circulatory practices of the past allows us to engage with the ways in which modernity has been formed through its pre-histories.