The work of Stephen Dwoskin (born 1939 in Brooklyn, died 2012 in London) is varied in form, subject matter, and genre. He is best known for his early underground films, his seminal book Film Is . . ., and his role in setting up the London Film-Makers’ Co-op. This chapter explores his artwork through the films Chinese Checkers (1965), Trixi (1969), Dyn Amo (1972), Central Bazaar (1976), Trying to Kiss the Moon (1994), and Grandpère’s Pear (2003), which span his life and demonstrate the breadth of his oeuvre. These provide an examination of Dwoskin as an intermedial artist who came to artistic maturity in the multimedia New York Underground of the early 1960s, and whose practice was informed by, and often incorporated, other art forms, such as dance, painting, performance, avant-garde theatre, literature, and music. Through close readings of film works as well as historical contextual analysis, this medial multiplicity will be shown to be an artistic embodiment of the layered complexities of any person’s life: the relationship between the individual, the family, and ethnic and national tradition; the interplay between the artist and histories of art; the conflation of varied temporal, spatial, and even metaphysical coordinates; and the paradox of the organic individual using impersonal reproductive technology to record and provide access to a life.