The debate over contemporary Chinese avant-garde theatre tends to focus on its compatibility with popularization, which has led to a lack of attention to its political radicalism. Stemming from late nineteenth-century utopian socialism, the history of the avant-garde in Europe is one of constant, dynamic interactions between political and artistic radicalism. Although contemporary Chinese avant-garde theatre arose as a revolt against the political radicalism of socialism, it is also uneasily entangled with China’s socialist legacy. Not only did contemporary Chinese avant-garde theatre artists inherit the linear, progressive, and anti-traditionalist mindset from socialism, but, in contrast to their counterparts in Russia and Eastern Europe, their theatrical praxis also revolved around it. Through a close analysis of three prominent avant-garde theatre artists — Mou Sen, Meng Jinghui, and Huang Jisu — this paper argues that contemporary Chinese avant-garde theatre is defined more by its uneasy entanglement with China’s socialist legacy than its controversial relationship with market popularization. While Mou decidedly and defiantly broke away from socialist realism, socialism remained an indispensable reference point. For Meng, socialism was at once a target for mockery and an object of nostalgia. In sharp contrast to both, Huang strove to revive the revolutionary legacies in his avant-garde theatre.