Zen Buddhist aesthetics provide a framework for understanding Song Dynasty calligraphy, where principles such as spontaneity, impermanence, non-duality, emptiness, and effortless action are reflected in brushwork, composition, and artistic execution. Calligraphy was not merely an artistic form but a meditative and philosophical discipline, embodying Zen ideals of spontaneous movement and intuitive awareness. Each stroke embodied the artist’s present state of awareness, transforming calligraphy into a spiritual exercise rooted in Zen thought. This study examines how Zen philosophy shaped artistic execution and creative intent in Song Dynasty calligraphy, exploring the balance between control and spontaneity. A key objective is to compare Zen and Western artistic traditions, analyzing how Zen aesthetics challenge conventional notions of intentionality, authorship, and artistic mastery. The study also investigates how negative space (Śūnyatā) functions as an active compositional force and how logical modeling can explain the paradox of artistic spontaneity and control. A historical-philosophical and aesthetic approach integrates textual analysis of Zen and calligraphic treatises, semiotic interpretation of brushstrokes, and logical modeling to examine artistic intentionality. Computational tools such as Python (Matplotlib) are used for visual analysis, merging traditional aesthetic inquiry with contemporary data visualization methodologies. The study finds that Song calligraphy embodies Zen’s non-dualistic approach, where artistic mastery arises through mindful creation rather than rigid control. Negative space plays an active role in composition, and logical models demonstrate how Zen calligraphy dissolves dualistic constraints. This research offers a unique integration of Zen aesthetics, comparative philosophy, and computational modeling, advancing discussions on artistic intentionality, spontaneity, and meditative creativity in both historical and contemporary artistic contexts.