This essay revisits the issue of flatness, typically associated with teleological readings of modernist painting. At its outset, the text highlights a paradox: that some of the most powerful and prestigious accounts of postmodernism, including Frederic Jameson's, identity flatness-the modernist trope par excellence-as postmodernism's distinguishing feature. In an effort to untangle this contradiction, a new genealogy of flatness is proposed. Firstly, a powerful link is noted in Greenbergian modernism between optical flatness and psychological depth. Secondly, a preoccupation with the appropriation and reframing of stereotypes is identified in more recent art. Here, the psychological depth tied to optical flatness in modern art is itself deflated, producing a marriage of optical and psychological flatness. These transformations in the meaning surface and superficiality are traced through the art of Jackson Pollock, Jasper Johns, David Hammons and Kara Walker.