In this paper, I examine the work of Hassan Musa, a Sudanese painter, art historian and art critic whose concerns about contemporary geopolitical situations manifest in his work. Musa appropriates figures from heavily disseminated media images and “masterpieces” of art’s history, carefully orchestrating their relationships onto pre-printed fabrics. In this way, disparate elements like prostitutes, motorcycles, bananas, and American flags come together as riddling critiques. In particular, I focus on the painter’s Great American Nude series. Here Musa points to connections between European colonialism and the war on terror in his juxtaposition of Osama Bin Laden, Édouard Manet’s infamous Olympia and actors from the Abu Ghraib torture scandal. In the process of transposing Arab for white or man for woman, he challenges the notion that power resides among particular races, genders, and nationalities, instead highlighting the role of economic and political power in cleaving difference.