This article explores the racial politics of trolling by examining virtual world raids conducted by users of the internet message board 4chan. Since these raids deploy offensive language and imagery that play upon African American stereotypes and history, they can be understood as participating in an ironic, post-political racism that masquerades as enlightened yet maintains online spaces as bastions of white heterosexual masculinity. Moving beyond this frame, however, this article looks awry at these performances and considers how they might also be understood as unintentional yet productive interrogations of racial politics and logics within game cultures and technologies.