This paper analyzes the early years of the influential art journal October. Beginning in 1976, October established itself as arguably the foremost art-critical voice of postmodernism. Significant essays, published between 1976 and 1981 on the index, the expanded field of sculpture, allegory, and photography, served as trajectories leading to a deeper understanding of postmodernism and an emergent generation of artists skeptical of their late-modernist inheritance. However, this paper contends that October did not merely report and analyze then-recent cultural developments, but rather actively contributed and constituted those developments through a dialogical relationship between critics and artists. Therefore suggesting that any critical-historical reappraisal of postmodernism would be incomplete without apprehending October’s collaboration with artists in moving beyond late-modernism, this paper aims to demonstrate that much of our contemporary sense of what comprises postmodernism for the visual arts is fundamentally rooted in the intellectual positions advanced by October during 1976–1981.