For nearly 40 years, according to this author, "follow the money" has been an axiom in both journalism and politics--although, as Shakespeare might complain, one "more honour'd in the breach than the observance." It is useful to resurrect the axiom in analyzing the multimedia buzz and policy debates swirling around the movie "Waiting for 'Superman'." In education, as in so many other aspects of society, money is being used to squeeze out democracy. "Waiting for 'Superman'" and its surrounding campaign reflect an influential trend that has proved adept at dominating education policy in both Republican and Democratic administrations. This bipartisan alliance unites 20th-century conservatives closely aligned with the Republican Party, who made the bulk of their money before the dawn of the digital era, and 21st-century billionaires more loosely aligned with the Democratic Party, who generally made their fortunes through digitally based technology. These two groups can be described as analog conservatives and digital billionaires. The author states that these groups use their wealth to effectively control the U.S. Department of Education and to dictate reform. The alliance is evident in "Waiting for 'Superman'" and in the transformation of the charter school movement that the film champions. This article presents an investigative report on the analog conservatives and digital billionaires behind the film's interlaced marketing and political campaigns.