Abstract: Through the analysis of Zhang Daqian’s Picture of the Layman Dongpo in Bamboo Hat and Clog, the authors of this paper have found that, from the surface, the Su Shi’s image under Zhang Daqian’s painting brush is the expression of his wish to wander in the painting circle in China as a transcendent scholar.Nevertheless, this has shown his helplessness in the commercialized painting circle.And the self-image who begs in the street in the Picture of a Beggar in the Human Worldis the humorous self-mockery as well as the summary of his life.As a typical figure in the transformation from a traditional scholar to a“modern intellectual”, Zhang has expressed the joys and sorrows he experienced in his life from different aspects.