This article argues that Thomas Pynchon’s Vineland (1990) aligns the corruption of underground filmmaking to the corruption of west coast radicalism by way of a system of metaphor concerning media that is based upon an engagement with Orwell’s Nineteen Eighty-Four (1949). Pynchon delineates between two components of the filmic object – its metaphorical status as a medium of time and its affective nature upon the spectator. As a medium of time, the act of filmmaking is the act of producing memory and history. Aware of this, the radical film collective depicted in the novel attempt to counter the ‘government-defined history’ piped through television and mainstream movies. However, these nineteen-sixties radicals find their films corrupted by the state and eventually succumb to the affective nature of the mass media. By the 1984 of Pynchon’s novel, the former activists have become subservient to state-endorsed ideologies, reflecting a wider shift in the reality of American society across this time period. Following close textual analysis that uncovers the dialogue between Pynchon and Orwell in regards to the above, the article then addresses how the former characterizes the activists he depicts, and whether he expresses any optimism towards a revival of the American radical tradition.