Since the recent state crackdown on effeminate stars labeled as niangpao (sissy pants), “insufficient” masculinity has once again become a focus of political controversy in China. Among these stars, Zhou Shen, a male pop singer known for his feminized voice and image, continues to enjoy immense popularity and perform in official programs. His growing fame and tolerance by the state call into question his cultural-political strategy. Conceptualizing Zhou’s androgynous performance as a political effect of a series of co-optation, compromises and negotiations, this essay offers a contextualized reading of the complex ways in which competing and contradictory influences shape his expression. In tracing the practices that configure his stardom, we investigate how Zhou’s androgyny paradoxically reaffirms and unsettles hegemonic norms in non-antagonistic ways. We describe how his engagement with Xi Jinping’s China Dream creates an ambivalent space for negotiating established norms. We argue that Zhou’s phenomenal success rests with the fusion of contradictory elements into his performances and his ability to cut across binary classifications. This process has nurtured a politics of ambivalence marked by ambiguity, confusion and contingency. It also sheds light on the limit and possibility of doing gender politics in an increasingly illiberal setting.