Abstract: Cai Gen Tan, a book of proverbial-style essays composed in late Ming period, has charmed the world following its “craze” in Japan in the eighties of 19th century. Since the first translation into English in 1926, more than ten English versions of Cai Gen Tan has been published. However, the study on the English translation of Cai Gen Tan is far from enough. The author sorts out three key translations during the collation of its English versions, and carries on a comparative analysis in terms of vocabulary, discourse and version design, which will lead to a discussion on problems concerning English translation of Chinese classics, such as the translation of culture-loaded words, rhetoric and paratext.