In recent years, artificial intelligence (AI) has increasingly intersected with traditional art forms, introducing new modes of creativity that challenge established esthetic frameworks while expanding the boundaries of artistic expression. Against this backdrop, this study explores the transformative role of AI-generated randomness in Chinese calligraphy, an art form deeply rooted in the philosophical ideals of harmony and balance derived from Confucianism, Daoism, and Buddhism. By leveraging models like Stable Diffusion, AI infuses unpredictable elements into calligraphic creation, challenging established esthetic norms while unlocking novel artistic possibilities. Employing a cross-case comparative and textual analysis approach, this research examines visual-semantic contrasts between representative traditional scripts and AI-generated works, while also investigating the historical evolution of calligraphic esthetics, cultural practices, and cross-cultural reception. The findings reveal that such technological interventions enhance the global accessibility of calligraphy, resonate with younger audiences, expand its dimension of expression, and redefine human engagement with the art form. Results indicate that AI not only democratizes calligraphy but may also stimulate public interest in, and a deeper understanding of, traditional techniques and cultural depth. This study advocates for a dynamic balance between cultural heritage preservation and technological innovation, proposing AI as a cultural gateway to traditional practice, and calls for further exploration of its global cultural implications.