Wang Kai-yun was an important gentleman in Tainan during the Japanese colonial period and Post-war ROC period. In addition to receiving the new Japanese education, he was also influenced by the sinology of his father, Wang Dong. He was a Taiwanese intellectual whose career spanned across the old and new. After graduating from the Mandarin school, he served as a discipline officer in a Japanese public school. Afterwards, he changed his career, entered the fields of business and industry, and further branched out into politics. Although he was successful in both political and business circles, he never discontinued expressing his preference for literature and art. Han poetry was his favorite, and he wrote about four hundred Han poetry. Most of the poetry was written for expressing his will such as "satirizing the government and expressing concerns with current events by using metaphors." Moreover, Wang was one of the founders of an important publication in Tainan, the San Liou Jiou Tabloid. When he served as the director and editor of San Liou Jiou Tabloid, he wrote a column for the Tabloid, and also published his works such as novels, short plays, and comical articles. His performance of literature was quite abundant and diversified. Based on The Complete Works of Wang Kai-yun published in 2009, this paper explores how Wang behaved during the Japanese colonial period by investigating his writings of Han poetry and essays. This paper also analyzes his thinking based on his "concern" and "carefreeness." It is hoped that his hidden sentiment of life and in-depth introspection and concern with the time and society under his title as a gentleman and celebrity could be presented.