The cultural accomplishments of the Northern Song dynasty are unrivalled in Chinese history. Song literati were particularly enthusiastic about calligraphy and writing materials, and the scale of their engagement in the art of writing exceeded that of both former and later dynasties, leaving plentiful legacies of calligraphic culture for later generations to study and appreciate. However, most modern studies emphasize the transmission of calligraphic culture from the Tang to Song and neglect the dynamics of disconnection and transformation between these two dynasties. By demonstrating how the technologies of brush, paper, ink cake, ink stone, and chair and desk (the "materiality" of calligraphy) shaped the look of calligraphy, this dissertation proposes an alternative understanding of the nature of Song innovations in the art of writing. Insofar as these innovations reconfigured the subsequent history of Sinitic calligraphy (calligraphic traditions based on Chinese characters), this dissertation argues that we cannot understand the art of writing without exploring the technology of writing. Through this study, I present the processes by which the literati of Northern Song traced, received, and modified the calligraphic culture of the past in creating their own Northern Song culture. Because of cultural discontinuity and transformation, what they ultimately reconstructed served as the foundation for their own culture, and has become the basis for how we think of the pre-Song past.