In the 1920s, modernist art and philosophy shared cinema’s ambitious project to refashion representations of subjectivity and time. Virginia Woolf was able to foresee that, in terms of representation, the cinema offered advantages literature did not have. By exploring the link between the advent of the cinema and what Woolf called “The New Biography,” this article explores the convergence between film theory, of adaptation in particular, and the theory of the New Biography as Woolf conceived it. Because Orlando: A Biography can be considered a mise en abîme of this theory, and because it lies at the crossroads between Woolf’s interest in the new visual medium and her search for a new mode of expression, its cinematic adaptation by Sally Potter in 1992 provides a particularly revealing insight into the problems of translation from one medium to another. The cinematic language of Orlando and its modernism led Potter to invent a new mode of adaptation as translation that is perhaps as challenging and innovative as Woolf’s original.