Although some scholars have successfully challenged the traditional biographical reading, which considers an author’s biography an important reference and proposed proper reinterpretations of many of Tao Yuanming’s poems, we still find its dominance in the interpretation of words and sentences, even the structure and theme in Tao’s poems. In light of this issue, this article reinterprets thirteen of Tao’s poems based on our detailed investigation of all the existing notes on them. Most biographical readings, shaped by the ideal image of intellectuals portrayed in the Analects, obscure the substantial connections with the Zhuangzi in Tao’s poetry. Our reinterpretation focuses on the intertextual relationship between Tao’s poems and the Zhuangzi. We can see that the influence of the Zhuangzi on Tao’s poetry is more extensive and far-reaching than previously considered. This can help us reveal the connection between Tao’s poetry and the metaphysical institution in the Eastern Jin dynasty, which took its view of life from the Zhuangzi, instead of taking Confucianism as the only source.