王開運是日治至戰後台南地區重要士紳。少時除接受日本新式教育，也受到父親王棟的漢學薰陶，是一位跨越新、舊世代的台灣知識分子。國語學校畢業後，曾任公學校訓導，其後轉進工商業界，進而跨足政壇。王氏一生雖得意於政商兩界，卻未曾中斷對文藝的喜好；特別是漢詩方面，留下近四百首作品，其中有為數不少屬感憤諷刺，憂時憫己，或托情寓物的言志之作。此外，王開運還是府城重要刊物《三六九小報》的創辦人之一。在其擔任《三六九小報》理事兼編輯期間，不僅為小報撰寫專欄文章，更發表了小說、短劇、滑稽短文等創作，文學表現相當豐富而多元。本文以2009年出版的《王開運全集》為依據，嘗試透過其漢詩和雜文的書寫，觀察這位府城士紳在殖民統治下的自處之道，並且從中拈出憂世情懷及其化解之道，作為本文論述分析的主軸，期望能呈現王開運在士紳名流的光環之下，隱而未顯的生命情調，及其對時代社會的深刻反思與關懷。

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.