The writings of East German author Wolfgang Hilbig reveal an indebtedness both to the poetics of Baudelaire and to literary modernism. At the same time, his creative oeuvre is shot through with intertextual references to German Romantic artists and tropes. Hilbig's attraction to the Romantic Movement is far from epigonal, sentimental or escapist. The article argues that just as the (re-)discovery of Romanticism during the 1970s and 1980s by other East German literary practitioners, including Hilbig's own mentor Franz Fühmann, resulted in a profound questioning of "actually existing socialism" and the cultural politics that shaped it, Hilbig similarly draws on Romantic topoi, intellectual discourses and aesthetic tenets to critique flaws in the State's socio-political mechanisms and in its treatment of the artist/writer. The article explores Hilbig's integration of philosophical, poetological and ecological aspects of this Romantic legacy into more than three decades of prose fiction and verse. It also interrogates Hilbig's reconceptualisation of Romantic imagery and diction.