In extant Chinese poetry, there are a considerable number of poems composed on the theme of “Observing Female Entertainers” from the fifth through ninth centuries. Through an examination of such poems, this paper traces the changes in male poets’ views of female entertainers: from placing female entertainers and their performances in a broader context of a pleasant moment, to focusing on the details of female entertainers and their performances, as well as from treating female entertainers as a medium for poets’ self-reflection to desiring intimate relationships with them. This paper shows how this change in perception and representation of female entertainers by male poets not only indicates the development of the entertainment system, but also evidences a new function of this subgenre of poetry.