This text looks at the work of South African artist William Kentridge, and the Russian artist Dmitry Gutov who’s works both represent change in their countries. Robbe examines How both artists imaginings of failure and how both artists draw on the absurd, putting them in conversation with one another, the author offers close readings of two works, Dmitry Gutov’s 2006 video ‘Thaw” with Kentridge’s installation “I’m not Me, The Horse is not Mine (2008)” and looks at how the artists recent works which examine “the failures of transformation since the 1990s, placing their concerns within transnational contexts and the longue duree of history” (3).