PAIN THINGS – this ambiguous title on his web site is how the painter and video artist Karl Nagel introduced his work. In the context of writings on Estonian art, his works are an ideal beginning for a chapter dedicated to the problematic contemporary artist, who takes provocative stands on questions of ideology and politics. It is not easy to write an overview of Karl Nagel. His paintings are often impressive, but in a way that transfixes the mind and inspires words that die on ones lips. Nagel does not concern himself with the traditional approaches to presentation in the local art scene nor the expectations prevailing in society. The story of this contradictory artist often begins at the moment he manages to render the oppressive and desolate context visually attractive - using description he overcomes the viewers distance, which is a protective device, and throws sense and reason into opposition. In his best works, Karl Nagel achieves authentic descriptions of death, guilt and war, all under the guise, saturated with negative references, of a politically engaged artist. His position as an artist revolves around terrorism, fascism and nationalism, and until recently, on issues dealing with the repression of ethnic minorities he has taken a non-nationalist stand. Some of Nagel’s treatments are outside the framework of political correctness. Even his own biography is presented like the saga of a dissident in the new age, the hero of which develops through the fire of contradictory experiences. One could claim that the roots of his negativity and dissidence lie in the traumas of Estonian society in the 1990s, and he considers the criminalizing of the corruption of that time necessary from his position as a dissident. While the standard dialect of Estonia in the transition period of the 1990s was largely based on an almost futuristic vocabulary, which had wrapped itself up in the rhetoric of constructing a better world, then Karl Nagel’s narrative, deconstructing official ideologies, results from consequences and traumas. As a punk-anarchist he believes he is above all giving expression to a revolutionary spirit through his work, which he wishes to express via verbal as well as artistic statements. In 2003, Nagel launched a virtual organization, New Era, on his web site, where he talks about the importance of free social criticism and the need to politicise all areas of life. Yet I feel that Karl Nagel has failed in the role of an anarchist executing Realpolitik, and that he does not provide us with any answers as to the steps we should take or what is to be done. Karl Nagel is a painter who operates within the territory of radical existential experience. He is an artist who finds liberating impulses from politics in order to iterpret his psyche as well as social realities. According to the dominant belief, it is no longer possible nowadays to present brutal political facts with the mediation of painting. Those artists who do try to do it usually fall into the same predicament as those who use their art to disseminate religious views. Both groups are forced to construct their ideologies through rooted orthodox iconographic examples.