As a constant element in Chinese landscape paintings, human figures of diminutive scale lend a sense of life and activity to mountains and waterways of immense proportions. In Song Dynasty (907-1279) landscape art, the emergence of new categories of human figures challenged the normative conviction that views them as aesthetically subordinate and dispensable. Differentiated from conventional types—fishermen, wood cutters, travelers, farmers, hawkers, et cetera—inhabiting landscapes out of utilitarian needs, the newly emergent figures, represented as roaming, gazing, listening, and being suspended in a moment, demonstrated a heightened sense of awareness to their surrounding environments.This dissertation conceives of such attentive subjects—not as an entry-point for artists or guide to experiences of landscape for audience—but as active participants that transformed the depicted landscape from merely an object of the appreciation of nature into a sympathetic field, a place where the acts of perception and interaction occurred and where the interiority or state of mind could be made pictorially manifest. It contributes to the study of Chinese landscape art a fresh look at the intervention of a mindful subject and how such figures can infuse the landscape with a personal vision that was palpable and sharable. The attentive subject of landscape emerged at the intersection of two streams of influence. First, landscape from the eleventh century onwards was increasingly conceived of as a means mediating the subjectivity of experience. Second, one’s attention and sensibility, especially as conceptualized in the Southern Song (1127-1279) discourses of philosophy and poetics, in place of the immanent order of the phenomenal world, became the empirical and cognitive foundation on which the coherence of reality was grounded. This study examines figure-in-landscape compositions spanning over two hundred years of production, from the last quarter of the eleventh century to the end of the thirteenth century. The introduction reviews the historical understanding and current discussions of human figures represented in landscape painting and theorizes the constitutive role of attentive subject. The main three chapters of the dissertation deal respectively with the wanderer’s debut in Song landscape art, with the gazer staging his self-conscious stance like an actor, and with an attentive subject’s sensory awareness caught in a suspended moment. Taken together, these chapters argue for the multivalent mediating spaces that landscape as a pictorial subject can offer in Song dynasty painting practices.