Background/Context: In "Citizens United vs. Federal Election Commission (2009)," the U.S. Supreme Court cleared the way for corporations to spend unlimited amounts of money to influence citizens' decisions about candidates and issues that will appear on election ballots. More important, however, for democratic educators, the ruling was grounded in an assumption that citizens can easily recognize "political speech" when it appears in media such as "Hillary: The Movie," the film at issue in the case. Purpose/Objective/Research Question/Focus of Study: This article examines implications of this ruling for democratic education. In particular, this article focuses on the nature of the documentary form in society, including how it is used toward political purposes and how teachers, students, and the public view it as an objective source of information in and out of the classroom. Research Design: This study is designed as an analytic essay that addresses a critical issue within democratic and media education and draws from a broad base of empirical, theoretical, and conceptual work to examine issues exacerbated by the "Citizens United" ruling. Conclusions/Recommendations: This article concludes that critical media education should be a core tenet of democratic education, especially as we move into the 21st century, and outlines areas to address in curriculum, pedagogy, and policy.