James Baldwin was a vocal critic of Hollywood, but he was also a cinephile, and his critique of film was not so much of the medium itself, but of the uses to which it was put. Baldwin saw in film the chance to transform both politics and art—if only film could be transformed itself. This essay blends readings of archival materials, literature, film, and print culture to examine three distinct modes in Baldwin’s ongoing quest to revolutionize film. First, I argue, literature served as a key site to practice being a filmmaker, as Baldwin adapted cinematic grammars in his fiction and frequently penned scenes of filmgoing in which he could, in effect, direct his own movies. Secondly, I show that starting in the 1960s, Baldwin took a more direct route to making movies, as he composed screenplays, formed several production companies, and attempted to work in both Hollywood and the independent film scene in Europe. Finally, I explore how Baldwin sought to change cinema as a performer himself, in particular during his collaboration on Dick Fontaine and Pat Hartley’s documentary I Heard It Through the Grapevine (1982). This little-known film follows Baldwin as he revisits key sites from the civil rights movement and reconnects with activist friends as he endeavors to construct a revisionist history of race in America and to develop a media practice capable of honoring Black communities.