In Hong Kong, despite its overwhelming capitalist logic, pop music makers have established a tradition of political engagement, stretching from the anxiety towards the 1997 Handover, the post-Tiananmen fury and fear, to the more recent articulations against increasing intervention of the Beijing regime. While previous chapters provide a textual analysis and explore the political engagement of Tat Ming Pair’s work—their songs, performances, and music videos—Chapter 5 will take a different approach by conducting a production analysis of Tat Ming’s 2012 and 2017 concerts. The concerts that took place in the Hong Kong Coliseum created a great buzz around the city of Hong Kong and were applauded for their political, musical, and aesthetic standards. This chapter zooms in on these concerts and asks: What considerations, negotiations, tensions, controversies, and compromises on the production side underpin the narratives and aesthetics of Tat Ming’s 2012 and 2017 concerts? As such, Chapter 5 aims to unpack the making of a political pop spectacle in a city that is struggling for its future. To do so, the chapter conducts a two-fold production analysis. First, the chapter builds on a discourse analysis of the reports that have emerged in different media platforms before, during, and after the concerts. Second, we will conduct interviews with Tatming and their close collaborators, ultimately reflecting on the tension between political motivations and commercial considerations, between engagement and entertainment. By drawing on John Corner’s (1999) levels of production, we will investigate how different makers and creative workers negotiate the tension between creating an appealing aesthetic spectacle on the one hand, while trying to convey a political message on the other hand. Our analysis distils three key discourses that we find salient and helpful in furthering our understanding of a concert production. We call them the contingent, the personal, and the calibrational. They recur in the narratives of the three producers and are interwoven through different levels of production.