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The political satirists Jon Stewart and Stephen Colbert are largely celebrated for their nightly television programs, which use humor to offer useful political information, provide important forums for deliberation and debate, and serve as sites for alternative interpretations of political reality. Yet, when the two satirists more directly intervene in the field of politics—which they increasingly do—they are often met by a chorus of criticism that suggests they have improperly crossed normative boundaries. This article explores Stewart and Colbert's "out of the box" political performances, which include, among others, the 2010 Rally to Restore Sanity, Colbert's testimony before Congress in the same year, and his on-going efforts to run an actual Super PAC that raises and spends money to influence (and critique) the political process. Examining these and other examples of non-traditional, and clearly border-crossing political satire, we consider the ways in which such multi-modal performances-in and off the television screen-work together to provide information, critique, and commentary, as well as a significant form of moral voice and ethical imperative. In turn, we examine the responses from the political and journalistic establishment, which more often than not, constitutes a form of boundary maintenance that seeks to delegitimize such alternative modes of political engagement. Finally, we discuss the significance of the developing relationship between television entertainment and political performance for our understanding of contemporary political practice.