This article considers some of the ways the cultural frameworks within which we create and dialogue are shifting in the twenty-first century, and how this might be articulated by emerging theories of ‘metamodernism’. It outlines some of the foundational issues to which metamodern theory speaks: hallmarks of postmodernism which have since become problematic within contemporary practice, exampled in approaches to painting landscape from the 1980s to 90s. The author considers the contradictions of postmodernism in relation to decolonization through aspects of critique that are both constructive and exclusionary. This leads to a broad overview of metamodern theory, outlining significant contributions to the field from a global perspective. It introduces some key ideas; simultaneity, depth, a ‘structure of feeling’ and a return to meta-narrative: characteristics of metamodernism which the article proposes as being first apparent in historical Land art. Through this lens the author articulates recent shifts in contemporary painting of/with and in landscape. Considering the resonances between Land art and painting in context of metamodern ideas, it is argued, contributes to cultivating a more embodied, non-essentialist, decolonized and outward looking approach to painting and landscape.