This article looks at Gerhard Gundermann’s use of the Krabat motif from Jurij Brězan’s novel Krabat or the Transformation of the World in his Liedertheater productions with Brigade Feuerstein in the GDR and, post-unification, in his solo songs. From Hoyerswerda in South-East Germany, Gundermann was simultaneously an open-cast miner and a singer/songwriter and dramatist who died prematurely in 1998 at the age of 43. Emerging out of the GDR singing club movement in the late 1970s, he relentlessly exposed the ruling SED Party’s monopoly on power in his work with Brigade Feuerstein. After German unification, as a solo performer, he became the mouthpiece of culturally disenfranchised East Germans. Twenty-five years after his death—in the wake of renewed interest in this performer as evidenced by Andreas Dresen’s film Gundermann (2018) and Grit Lemke’s documentary Gundermann Revier (2019)—it is time for a proper academic assessment of his work. This study breaks new ground, firstly in its analysis of the unpublished works of Brigade Feuerstein and secondly by exploring the extent to which Gundermann’s life work was underpinned by the philosophy of Krabat, in its exposing of humans’ exploitation of one another and their environment. In this, one can see how Gundermann created an aesthetic approach that successfully spanned two political systems.