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Focusing on the dynamics between negotiation and homogenisation in discourses about heritage, this paper provides a philosophical analysis of the idea of ‘medium of memory’, complemented with the case of the Festival of the Drunken Dragon in Macao, and attempts to demonstrate how an item of heritage can, in the course of its regular practice, be (re)mediated through different collective and individual memories. The motif of the ‘ouroboros’ is suggested throughout our analysis to compare with the self-perpetuating memory-mediating processes expressed in the emergence of ‘heritage’. Conceptualising heritage as a medium capable of being bestowed with differentiating narratives and memories allows us to come to an alternative perspective of ‘heritage’, that is both malleable and sustainable. Such a perspective also sheds light on certain abuses of ‘heritage’, such as the creation of simulacra.