This paper argues that the Zhuangzi《莊子》represents a specific type of Daoist practical philosophy: It is medicinal or therapeutic and seeks to promote existential ease, often by means of humor. Part of its approach to practical philosophy consists in pointing out the impracticality of many early Chinese philosophical doctrines, and, especially, Confucian political and ethical teachings. To illustrate this understanding of the Zhuangzi, the narrative of Confucius’ visit to the legendary Gangster Zhi (dao zhi 盜跖) is analyzed in some detail.