Taipei city is the capital of Taiwan, and the city government has applied to host several international events since 2000. Meanwhile, mayors have proposed the slogan “axis retroflexion” indicating the urban regeneration of old town areas. In July 2016, the city government and the National Geographic Channel started a documentary project “Inside: Reinventing Taipei” that cost 5 million NTD for the propaganda of the upcoming Taipei Universiade 2017. The narratives in the documentary indicate the interweaving of historical and modern city images. In this research, the development history of western Taipei is reviewed, and several official and non-official advertisements, movies, music videos, landscape architecture, events, and policy plans are chosen as texts to analyse the representation of the city images of western Taipei (Zhongzheng and Wanhua districts) under an iconological approach. To understand how those city images were produced, various aspects of urban politics and power are explored through this research. It is found that specific buildings and places, such as Chiang Kai Shek Memorial Hall, the North Gate, the Red House Theatre, Longshan temple, and the Ximending shopping area, appeared in those texts frequently, epitomizing the development history of Western Taipei and policies across different periods. The historical, cultural images are represented as buildings, and trendy, energetic commercial images are presented in the official representation, while negative images, such as the ruined, the hopeless, and the order-less, are presented in the non-official representations. Furthermore, with the political intention of “change,” the new governance institution selectively represents some “negative” images that have been absent in previous official representations to emphasize the differences between the old and new governance institutions. Generally, the city images and representations of western Taipei manifest the issues of power and visibility clearly.