Taiwanese geishas played a special role under Japanese occupation. Originally, they were only cupbearers in taverns. They became significant in the history of Taiwanese play for germinating woman play. Geishas that rooted in the economic development and prospering tavern business once flourished under Japanese occupation. The declination of geishas reflected the change of times. Geishas no longer exist at present time, but they were important in the history of Taiwan play or the histories of society. Based on the past researches, I try to trace characteristics of geishas under Japanese occupation by studying their origins, the forms and locations of their performances, and changes in their popularity. This paper will contribute to a clear and deeper understanding of Taiwanese geishas.