The invention of writing has allowed civilizations to be effectively preserved and passed down. However, many issues related to writing had emerged as diverse scripts and fonts became standardized, which altered the course of cultural history. The resulting shifts and changes deserve to be carefully examined, including the rise of Confucianism as main state ideology advocated by Emperor Wu of Han dynasty. This resulted in disputes between Modern Confucian Classics and Ancient Confucian Classics, which impacted the historiography of Han dynasty and dictated the course of its cultural history. The modern and ancient disputes encompassed more than just academic schools of thoughts and political interests; on the very surface, it debated over the issues of authenticity associated with writing. The Modern Confucian Classics consisted mainly of recounts by Han dynasty Confucian scholars, with general ideas of Confucianism thereby derived. On the other hand, Ancient Confucian Classics referenced unearthed literature, and re-edited to decipher the authenticity of the scriptures. Both sides demonstrated theoretical foundations with offensive and defensive objectives, but were both fundamentally focused on the cognition and examination of writing. Therefore, Shuowen Jiezi (literally “discussing writing and explaining characters”, an ancient Chinese dictionary from the Han dynasty) compiled by Xu Shen traced the evolution of Chinese characters, which became the cornerstone for Ancient Confucian Classics. It is not the intention of this paper to go into details on the debate over principles and connotations in Ancient Confucian Classics and Modern Confucian Classics, but the objective is to examine how writing and artistic aestheticism were impacted by the argument over the Confucian classics and their interrelated influences on writing. Furthermore, under the scope of Confucian Classics, analysis is made on how Chinese characters progressed from Confucian principles and evolved into calligraphy art through the gradual development of different and altered writing aesthetics. This paper departs from the value of writing explained by Confucian principles and examines the intrinsic differences between official writing style and everyday writing styles. Lastly, analysis is conducted on the developmental course of calligraphy art under the scope of traditional Confucian principles, and how its give-and-take relationship with Confucian Classics led to the parallel development of writing aesthetics and the art of calligraphy.