Abstract: The literati class during the Tang and Song dynasties played a pivotal role in the development of Chinese stone appreciation art. The frequent references to ‘stones’ in Tang and Song poetry offer invaluable insights into the evolving characteristics of stone appreciation among the literati. This study employs natural language processing (NLP) techniques, integrating both quantitative and qualitative methodologies—such as vector space models—to investigate the evolution of ‘stone’ imagery in Tang and Song poetry. It explores how the literati attributed multiple cultural and aesthetic meanings to stones. The findings reveal that Tang poetry placed emphasis on concrete, dynamic natural forms, viewing stones as symbols of tranquillity, the passage of time, and sacred transcendence, often reflecting profound Zen-inspired sentiments. In contrast, Song poetry adopted more introspective and symbolic interpretations, using stones as metaphors for reflecting on history and the flow of time. As a result, Tang dynasty stone appreciation art exhibited considerable formal diversity, with works ranging from simple, graceful forms with rounded edges to rugged, contorted pieces, alongside designs featuring pronounced linearity and sharp angular transitions. In contrast, Song dynasty art tended toward greater uniformity, pushing the boundaries of bizarre shapes to their extremes. By incorporating natural language processing techniques into the analysis of historical texts and artistic works, this study offers a fresh interdisciplinary perspective on Chinese stone appreciation, thereby contributing new insights to research on historical aesthetic art and imagery.