This essay examines Ken Jacobs’s landmark film Tom, Tom, the Piper’s Son (1969; revised 1971) in relation to a cluster of important critical writings about cinema and art by Annette Michelson written around the time that film was made. The essay argues that, during this time, Michelson saw cinema as poised to achieve parity with the other fine arts and fully realize its potential as the century’s defining art form. In this privileged moment, in which the lines demarcating different cinematic modes blurred, contemporary cinema appeared to Michelson as a summing up of film history, bringing together the major dialectical forces that had shaped that history for six decades: realism and modernism, illusion and anti-illusionism, engagement of the intellect and of the body. Her writings of this period evidence a metahistorical project, in which key individual films crystallized the interplay of formal tendencies and ambitions. This essay argues that, while Michelson did not write extensively about Tom, Tom, the Piper’s Son, she would have seen it as one of these “monumental” films that hypostasized this interplay and pointed the way toward cinema’s radical future. This essay analyzes Jacobs’s films in these terms, drawing upon Michelson’s writings on minimalist visual art, European and American art cinema, Hollywood cinema, and historical and contemporary avant-garde film.