Perhaps no one has had more influence on the role of political documentary in the contemporary public sphere than filmmaker Michael Moore. His unique melding of committed political arguments with an ironic reflexive style have changed the very look and feel of documentary film, contributing significantly to the form's newfound popularity. Furthermore, his steadfast commitment to progressive politics has given the issue of socioeconomic "class" the kind of attention it rarely receives within the mainstream media. However, Moore's films have also been the recipient of viscous attacks from his political opponents, and subject to some of the most contentious public debates over the documentary form since the 1960s. This study integrates documentary theory and poststructuralist discourse analysis within a critical/cultural studies perspective to map out the ways in which generic conventions, interpretive strategies and rhetorical maneuvers have often combined to undermine the political goals and cultural legitimacy of Michael Moore and his films. First, I look at the ways in which Moore's own deployment of a patronizing mode of address transforms his films into "fantasies of advocacy"; narratives that invite an imagined audience of fellow advocates to evaluate and judge the lives and behaviors of the working-class subjects depicted on-screen. Such a depiction only works to strengthen middle-class forms of social authority which have worked, historically, to encourage class resentment. Second, I describe the ways in which Moore is also undermined by a mass media system within which progressive views are not often welcome. I explain how a number of discursive logics worked to frame Moore at various times throughout his career as an untrustworthy documentarian pushing Leftist propaganda, as an "indie film auteur" providing innovative cinematic experiences to middle-class audiences, and as a savvy celebrity-huckster selling political entertainment to embattled liberals. Finally, I describe how Moore's opponents on the political Right exploited the problematic aspects of both his rhetorical strategies and public reception to paint Moore as a "Liberal Elitist," a move that worked to derail the political effectiveness of Fahrenheit 9/11 during the 2004 election. By describing the complex, public articulations of Michael Moore and his films, this study contributes to the fields of documentary studies, media studies, cultural studies and political rhetoric.