Sally Potter turned a novel long considered unfilmable into a period drama about one life lived across four hundred years, with Tilda Swinton as a nobleman who wakes up a woman.

Virginia Woolf published Orlando: A Biography in 1928, a mock life story written for and about her friend Vita Sackville-West, and for more than half a century it carried the reputation of a book nobody could film. Its hero lives for close to four hundred years, changes sex halfway through and treats English history as a run of costume changes. Sally Potter spent years trying to prove that reputation wrong, and Orlando, released in 1992 with Tilda Swinton in the title role, is the result: a period film that travels from the court of Elizabeth I to the end of the twentieth century in a little over an hour and a half.

The story opens with Orlando as a young nobleman whom the ageing Queen Elizabeth I, played by Quentin Crisp, rewards with a house and one condition: that he must not fade, must not wither, must not grow old. He obeys. Over the following century he falls for Sasha, a Russian princess played by Charlotte Valandrey, during a winter when the Thames freezes solid; he tries his hand at poetry and plays host to the writer Nick Greene, played by Heathcote Williams, who repays him with ridicule in print; and he accepts a posting as ambassador to Constantinople, where he befriends the Khan, played by Lothaire Bluteau. When violence breaks out around the embassy, he sleeps for days and wakes up as a woman.

The second half follows Lady Orlando back to England, where the same laws that once handed her estates now question her right to keep them. She passes through the literary salons of the eighteenth century, where Peter Eyre plays Alexander Pope, turns down a proposal from Archduke Harry, played by John Wood, and in the nineteenth century meets Shelmerdine, an American adventurer played by Billy Zane. The film then carries her into the early 1990s, with a child at her side and a manuscript to publish. Potter breaks the whole thing into titled chapters, Death, Love, Poetry, Politics, Society, Sex and Birth, and those headings do the work that a conventional epic would hand to transitions: decades disappear between them without apology.

Behind the camera, the project was an unlikely one. Sally Potter had trained as a dancer and choreographer and worked in performance art and experimental film before directing a feature, and her only previous one, The Gold Diggers (1983) starred Julie Christie. Orlando was a European co-production, with British, Russian, Italian, French and Dutch partners, produced by Christopher Sheppard, and much of its scale came from shooting abroad, with location work in Russia and in Uzbekistan, where the city of Khiva stood in for Constantinople. The film had its premiere at the Venice Film Festival in 1992 before its theatrical release.

Potter adapted the novel herself, and her changes are deliberate. Woolf ends her book in October 1928, the month of its publication, as a joke about a biography catching up with its subject; Potter moves the finishing line to the moment the film was made, so that Orlando reaches the present day of the early 1990s. The child Orlando has in the final chapter is a daughter, where Woolf wrote a son. And the satire of literary London, which takes up long stretches of the novel, is reduced to a handful of encounters, Pope and Greene above all, which keeps the running time near ninety-three minutes.

The casting of Elizabeth I is the most quoted decision in the film. Potter gave the role to Quentin Crisp, then in his eighties and best known for The Naked Civil Servant, his 1968 memoir of life as an openly gay man in London. A man playing the queen who tells a young man never to age mirrors what Woolf does with sex and costume throughout the book, and it signals early on that the film is not interested in the conventions of the heritage drama it borrows its settings from. The singer Jimmy Somerville appears as a singing angel in the closing chapter, another piece of casting that ignores the period-film rulebook.

For Tilda Swinton the role arrived at a turning point. She had come up through Derek Jarman’s films, among them Caravaggio, The Last of England and Edward II, and was a familiar face in British independent cinema rather than a name known to international audiences. Orlando gave her the lead in a period production with festival exposure and two Oscar nominations behind it, and the premise depends entirely on her: a single performer carries the character across four centuries and both sexes, with no change of actor at the midpoint. Her later taste for transformation and for long partnerships with auteurs is often traced back to this part.

The craft credits explain why the film is still discussed for its look. The cinematographer was Alexei Rodionov, who had shot Elem Klimov’s Come and See (1985); the costume designer was Sandy Powell, at an early stage of a career that would later bring her several Academy Awards; and the production designers were Ben van Os and Jan Roelfs, who had worked with Peter Greenaway. Powell’s costumes and the art direction by van Os and Roelfs earned the film its two Oscar nominations at the 66th Academy Awards. The score was written by David Motion and Potter herself, and the soundtrack album came out on Varèse Sarabande in 1993.

That pedigree has never settled the argument about the film, which has long split opinion between admiration for its design and doubts about its emotional pull. The structure goes some way to explaining both sides. Seven chapters covering four centuries means each relationship, with Sasha, with Greene, with the Khan, with Shelmerdine, gets roughly one chapter, and the film moves on before any of them can become the centre of the story. That is faithful to Woolf, whose novel is more interested in time and in the absurdity of English custom than in any single romance, but it asks the audience to accept a portrait in fragments rather than a love story.

The film also sits in a long line of attempts to put Woolf on screen. Marleen Gorris directed Vanessa Redgrave in Mrs Dalloway in 1997; Stephen Daldry’s The Hours (2002), adapted from Michael Cunningham’s novel, built a film around Woolf herself and earned Nicole Kidman an Oscar for playing her. More recently, the philosopher Paul B. Preciado returned to the same book with Orlando, My Political Biography (2023), a documentary in which trans and non-binary people each take on the role. Potter’s version remains the reference point those later films answer to, because it was the first to take the novel’s central conceit literally.

Both careers kept going in the direction the film suggested. Potter followed it with The Tango Lesson (1997), in which she starred herself, then The Man Who Cried (2000), Yes (2004), Ginger & Rosa (2012) and The Party (2017), mostly small, formally adventurous projects with large casts of name actors. Swinton went on to win an Academy Award for Michael Clayton and to build one of the most varied filmographies of her generation, moving between Hollywood franchises and directors such as Jim Jarmusch, Luca Guadagnino and Wes Anderson.

More than three decades on, Orlando is easier to place than it was in 1992. It is a costume drama that keeps undercutting the costume drama, a literary adaptation that rewrites its own ending, and the film in which Tilda Swinton first held the centre of an international production. Whether its chapters add up to a story or to a gallery of beautifully dressed tableaux is a question viewers still answer differently, and the film seems designed to leave it open.