This dissertation examines a small selection of the hundreds of films made by Andy Warhol and his collaborators between 1963 and 1968. Each chapter contextualizes a particular aspect of Warhol's filmmaking in terms of the artistic and cultural circumstances that informed it. Through an analysis of the content of specific films, rather than just their formal or stylistic tendencies, I discuss how the filmmaking process might have functioned for those involved in the films' production, as well as how those films might have functioned for specific spectators. The first chapter is a speculation on how Warhol might have understood filmmaking as a method for creating concrete connections between feelings and things -- for collecting imagery with his camera in order to create a historical catalog of people and their emotions. This first chapter also considers how some art critics in the 1960s used Warhol's early silent films as exemplars for their own anti-formalist art-historical and critical discourses. The second chapter examines the relationship between Warhol's films and the proliferation of amphetamine use amongst his collaborators. Amphetamines functioned to perpetuate for its users a way of life based on an alternative conception of time, and often involved a continued engagement with bad feelings, which fueled much of the creativity of the artistic community whose locus was Warhol's Factory in the mid-1960s. As such, many of Warhol's films from this period exhibit what I term an "amphetamine aesthetic" -- visual clues that suggest the effects of long-term amphetamine use by its participants. The third chapter is an analysis of a single film, Lonesome Cowboys. Participants in the film's production used the conventions of the Hollywood Western film genre to create a circumscribed space for transforming their everyday lives and their relationship to contemporary politics in the late 1960s. All of these chapters explore the effects of Warhol's particular approach to filmmaking, which involved Warhol's own detached style of directing, as well as his cultivation of an ultrapermissive environment in which his collaborators -- actors, directors, writers, and technicians -- felt free to experiment. This environment was predicated on the idea that the boundary between the space in front of the camera and the world beyond it was simultaneously arbitrary and deeply imbricated. Such a fluid boundary between the world inside and outside the scope of Warhol's camera is in part why some spectators, watching his films a half-century after they were made, might still find new meanings for the present in the films themselves. / text