Central to the work of Wen Zhengming (1470–1559) is the interrelationship between “places” as subject matter and “place” as a pictorial concept in landscape representation, mediated by the notion of jing (scene), which implies both situational experience and painterly ideal. Focusing on Wen’s late work, this dissertation examines the real-life experiential grounding of artistic production and consumption in relation to changes in landscape painting’s morphological and compositional significance during the sixteenth century. In both the representation and compositional use of jing, Wen promoted the principle of buzhi (relational positioning). This practical skill and formal-structural conception that was concerned with how to arrange things in bounded space then became a primary criterion for assessing artistic intelligence and creativity. The same principle was used concurrently in garden-building and everyday landscaping in the increasingly urbanized environment of the Suzhou area, where the artist lived. The artistic attention to relational positioning accorded with the transformation of social grids in a changing economic situation and political climate. Through exhaustive research into Wen’s networked art world, rediscovery of understudied artworks, and an interpretative framework that correlates artistic practices with social-historical and epistemological issues, this dissertation establishes some elements for a new understanding of early modern Chinese painting. Chapter One provides a critical analysis of the concept of jing in order to shed light on the historical notions of the “real” and the “scenic, ” and how the return to reality connects to the return to antiquity in the intellectual, literary, and art world of the time. Chapter Two investigate the significance of composition and its correlation with practical learning. Chapter Three examines the role of tree as topos and tectonic form in place-making and the pictorial imagination. Chapter Four discusses the path as formation of a “footfield” in Wen’s paintings through analyzing the spatiotemporal contingencies of the path motif as it negotiates the relations among compositional substructure, figural locomotion, and spectatorial engagement. Chapter Five highlights an overlooked genre of birthday-congratulatory albums depicting specific places, created by and for members of Wen’s social network, which situate personal experience in communal space and dynastic time. By reconsidering modern art history’s foundational assumption that landscape operates between the poles of idealizing subject and topographical description, this dissertation strives to fundamentally reassess early modern Chinese art and visual culture.