In this article, a semiotic approach is proposed to explain how human agents use and give meaning to art in complex contexts. Inspired by the psycho-historical approach on art appreciation, which attempts to embrace psychological and cognitive aspects of art sense-making, as well as the art-historical context dependence of artworks, an extended theory is suggested: an agent’s art use and interpretation can be described using three general categories of meaning grounding: phylogenetic recurrence, ontogenetic recurrence and collective recurrence. These categories explain how a certain meaning of a sign is possible and justifiable, supported by human agents’ capabilities and purposes. This article also proposes that it is possible to narrate, using such categories of meaning grounding, how different agents enact art, that is, give meaning and act upon art in different circumstances. Finally, I offer some examples about how the model can be used in real art contexts. The objective of this narrative-enactive approach, even though it offers a limited and edited focus, is to offer an orderly and comprehensible method to explain the dynamic nature of art meaning and how biologic, individual and collective grounding and purposes intertwine.