Classical Chinese literary thought features a long-standing debate over the essence and value order of literature and Dao. Confucius set a paradigm centering on moral cultivation， holding that literature completes Dao and Dao reveals itself through literature. During the Wei-Jin and Six Dynasties， however， literary practice shifted toward lyrical ornateness， elevating literary value while alienating Dao and splitting their inherent bond. Efforts soon emerged to redress this deviation and reconstruct the literature-Dao view. Liu Xie 刘勰 and Tang-Song prose masters upheld the literary mind and advocated integrating Dao via literature， laying groundwork for literary autonomy. Pei Ziye 裴子野 and Song Neo-Confucians prioritized the Dao mind， evolving core arguments from literature conveying Dao to literature harming Dao and finally literature deriving from Dao. They philosophically reconstructed the literature-Dao nexus under the substance-function framework. The classical literature-Dao view thus follows a dialectical trajectory： construction-deconstruction-reconstruction， a cycle of thesis-antithesis-synthesis. Faced with the perennial tension between rational principle and human sentiment， neither the proponents of literature nor the guardians of the Dao offered a rigid dogma. Instead， they forged a tradition of seeking balance amid tension and breakthrough amid dilemma. This legacy offers profound historical insight for pursuing a rational yet emotionally fulfilling good life.