Visual art representing perpetrators of genocides raises both aesthetic and ethical dilemmas. Why are these figures deemed worthy of representation? How does the medium or the style of representation create meaning and influence understandings of perpetrators? To what extent do factors such as the artists’ biography, the historical context, and the site of display influence critical understanding of perpetrators? Can one view without being guilty of “getting too close” to the perpetrators? This chapter addresses such dilemmas as it lays out a typology of artistic representations of perpetrators following a chronological approach, starting with the onset of the exterminatory policies of Nazi Germany, during and after World War II and the Holocaust period, and continuing into the 1990s and the 2000s. The cited works are discussed comparatively, by exploring representational similarities or differences in art depictions of perpetrators of more recent genocides in Bosnia, Rwanda, Cambodia, or Darfur. This chapter intends to open a critical engagement with artwork dealing with the perpetrators to address uncomfortable truths such as tendencies to mythologize, aestheticize, and normalize the perpetrators in popular culture.