This article explores the concepts of pain and agency in the photography series Case History (1997–1998) by the Ukrainian photographer Boris Mikhailov, and in four performance-actions (2012–2014) by the Russian performance-activist Petr Pavlensky. Although they represent different generations and respond to different historical contexts, Mikhailov and Pavlensky share a focus on the wounded body. Taking both the documentary and performative aspects of these artworks into account, Nordgaard argues that the wounded body stands forth as a body of agency which also reflects the social, political, and historical settings in which it exists. The relational consideration of the two artists therefore offers important insights for understanding post-Soviet Ukraine and present-day Russia, and reflects on the correlation between the private and the public body. By placing Mikhailov and Pavlensky in dialogue with a broader discussion on spectatorship and the role and significance of “shock imagery” and spectacle in contemporary media, the article further suggests why artworks depicting the body in pain have both an ethical and political function.