Documentary film is an increasingly popular genre and due to cheap filmmaking technologies, there are more documentary films being produced than ever before. Yet, despite the democratization of production, documentary filmmakers still face a number of challenges when it comes to funding, producing, and distributing their films. Copyright issues are a popular area of focus, but the cost of copyright clearance is not the only difficulty facing filmmakers. This qualitative study of documentary filmmakers explores the particular challenges faced by documentary filmmakers in Boulder and Denver, Colorado and places them in the context of historical figures and films of the documentary genre. The study finds that in addition to issues pertaining to copyright and the First Amendment, documentary filmmakers face a number of challenges in the documentary film marketplace, including fewer opportunities for public funding, less security in finding distribution, and increased competition from and pressure to adopt the visual language of reality television. This study provides a starting point for future research on documentary film communities and the political economic issues that affect them