This essay examines the conditions shaping cinema’s emergence in the early twentieth-century American penitentiary. Cinema entered a prison environment in which the programming of film alongside other popular entertainments, such as lectures, concerts, vaudeville, and musical performances, persisted longer than in the wider society. The essay considers how cinema and other portals to the outside world, such as magazines, books, and newspapers, affected the balance of the senses; the popular press’s fascination with the idea of carceral spectatorship as an alternative to traditional models of a fee-paying audience; and cinema’s role within the “coddling” debate. By the late 1910s, Sing Sing prison, located thirty miles north of New York City, held nightly film screenings and frequently served as a film location for commercial film companies. This essay examines the interlocking institutional, carceral, and imaginative structures that made filmgoing possible for the fifteen hundred inmates in Sing Sing in the early twentieth century.