This dissertation explores metamodernism in contemporary culture, focusing on its manifestation in literature and its intersections with vaporwave and the music of Radiohead. It considers the novel Taipei by Tao Lin as a representation of metamodern sensibility, analysing its portrayal of a human subjectivity navigating a world shaped by digitisation and market forces. Furthermore, this dissertation delves into the aesthetics and cultural implications of vaporwave, highlighting its nostalgia for banal spaces and its subversive and transformative potential. It also explores Radiohead’s music as an embodiment of metamodern themes, particularly modern anxieties and Radiohead’s distinct ability to evoke both despair and hope. Drawing on concepts from thinkers such as Jameson, Deleuze, and Guattari to illuminate the formulation of metamodernism as an emerging school of thought, this dissertation aims to establish a sound theoretical underpinning to afford more validity to considering these multi-modal texts as having potent and significant scholarly implications. Overall, the dissertation aims to assert the utility of metamodernism as a theoretical framework and critical lens for observing developments, both emerging and established, in popular and literary culture.