This article seeks to investigate art in public urban space via a process of activating aesthetics as a way of enhancing pedagogies of engagement. It does this firstly by addressing the question of aesthetics in Enlightenment and twentieth-century frames; then it seeks to understand how artworks may be approached ontologically and epistemologically. The discussion works with the philosophical lenses of two different thinkers: Heidegger, in ‘Building Dwelling Thinking’ and ‘The Origin of the Work of Art’, and Marxist sociologist, Bourdieu with his work on a theory of practice and habitus. It asks how art may work in the meaning-making processes of place and the human subject in terms of ontological difference (Heidegger) and dispositional capital (Bourdieu). In bringing these different organising principles of interpretation to specific works of art, the discussion draws from locational research undertaken in Newcastle/Gateshead and Melbourne.