This paper aims to survey the oeuvre of Kwon Yeo Hyun, who is considered a representative artist of Korean postmodern art, and to reveal its meaning in the context of contemporary painting theory. In examining Kwon’s art over the past four decades, which has spanned painting, drawing, photography, video, performance, and installation, I will focus specifically on the concepts of “self” and “performativity,” as I believe these two concepts consistently underpin his diverse practice. From his early works influenced by existentialism to recent works associated with post-structuralism, Kwon’s art is not limited to a single style. His exploration of the self has expanded to include the social self and the other, combining history, mythology, and philosophy, and is realized through various layers of performativity that unfold on and off the canvas. In other words, Kwon’s performativity encompasses self-consciousness as an artist in a constant state of transformation, disguise performance, “sensory drawing” that is directly related to physicality, and network through collaboration. In considering the status of painting in the post-medium era, Kwon’s artistic practice can be discussed in relation to the views of Isabelle Graw, who emphasized the indexicality of painting and painting as a thinking subject, and David Joselit, who focused on painting as a node in social networks.