The film adaptation of Orlando: A Biography was almost never made. In the late 1980s and early ’90s, studios roundly rejected director Sally Potter’s vision to bring Virginia Woolf’s 1928 novel to the screen: It wasn’t adaptable; it wasn’t sellable; it was too costly to make. But Potter had already recruited then-up-and-coming actress Tilda Swinton to play the titular, young British nobleman who lives for three centuries and inexplicably wakes up as a woman at age 30.
The director asked Swinton if she would collaborate on a series of photographs—maybe if producers could see her vision, they would believe it possible. So they traveled to the childhood estate of Vita Sackville-West—Woolf’s lover and friend, and the basis of the protagonist’s character—in Kent, England, and Swinton first stepped into the role of Orlando.