This thesis re-investigates Clement Greenberg’s discredited abstract expressionist claim that painting should seek its own purity through the acknowledgment of its material. I argue that Greenberg’s physical, bodily determination of painting (but not its purity) is re-located as a criticality in contemporary practice because of the changes brought about by the simulacrum and the digital. By utilizing the particularities of ‘painterly’ issues such as materiality, depth and opticality into the virtual, this claim responds to Arthur C. Danto’s ‘end of history’ theories where he argues that artists are no longer bound to the dictates of grand master narratives of art. For Danto, contemporary art has irrevocably deviated from the narrative discourses which define it such as Greenberg’s. Not satisfied with either postmodern strategies of parody in painting that claim a linear end to the modernist canon, or with recent claims that contemporary painting is beyond postmodernism, I convert Greenberg’s physical determinism using Andrew Benjamin’s notion that contemporary abstract painters, through making, accept and transform the historical/modernist premise of the yet-to-be-resolved object/painting by staging a repetition of abstraction as an event of becoming. This ‘re-styling’ of abstract painting is then examined as an ontological conjoining of Greenberg with Merleau-Ponty’s claim that the painter transforms the relationship between the body and a painting by overlapping the interior sense of self with the world of external objects. I argue that contemporary painting can offer a philosophical dialogue between the painter’s subjectivity as a mirroring of the painter’s personal style through objective ornamental materiality. This dialogue is developed through Stephen Perrella’s Hypersurface theory which proposes a non-subjective, deterritorialised, architectural parallel of the digital as a transparent, fluid system of multi-dimensional signs in which the contemporary subject traverses. Consequently, I suggest, the symbolic virtual changes the body’s sensuous relation to time and space and is central to contemporary painting’s criticality.