It was particularly acclaimed for its visual treatment of the settings of Woolf's 1928 novel. Potter chose to film much of the Constantinople portion of the book in the isolated city of Khiva in Uzbekistan, and made use of the forest of carved columns in the city's 18th century Djuma Mosque.
The film premiered at the 49th Venice International Film Festival, in which it entered the main competition. Orlando was re-released for screening in select cinemas in August 2010.
The film begins in the Elizabethan era shortly before the death of Queen Elizabeth I. On her deathbed, Elizabeth promises an androgynous young nobleman named Orlando a large tract of land and a castle built on it along with a generous monetary gift which she will only bequeath to him if he consents to her command, "Do not fade. Do not wither. Do not grow old." Both he and his heirs will keep the land and inheritance forever. Orlando acquiesces and resides in splendid isolation in the castle for a couple of centuries, during which time he dabbles in poetry and art. His attempts to befriend a celebrated poet, however, backfire when the poet ridicules his verse. Orlando then travels to Constantinople as English ambassador to the Turks, where he is almost killed in a diplomatic fracas. Waking up the next morning, he learns something even more startling: he has physically transformed into a woman overnight.
The now Lady Orlando comes home to her estate in Middle Eastern clothing, only to learn that she faces several impending lawsuits arguing that Orlando was a woman to begin with and therefore has no right to the land or any of her/his royal inheritance.
The succeeding two centuries tire her out; the court case, bad luck in love and the wars of British history eventually bring her up to the 1990s, with a young daughter in tow and a book in search of a publisher. The editor who judges the work as "quite good" is, ironically, portrayed by Heathcote Williams – the same actor who denigrated her poetry as a different character 200 years earlier. Having lived a most bizarre existence, Orlando finally finds a tranquil niche within it.
Director Sally Potter said: "My task with the adaptation of Virginia Woolf's book for the screen was to find a way of remaining true to the spirit of the book and to Virginia Woolf's intentions, whilst being ruthless with changing the book in any way necessary to make it work cinematically. [...] The most immediate changes were structural. The storyline was simplified – any events which did not significantly further Orlando's story were dropped."
The film contains anachronisms not in the novel. For example, on arrival in Constantinople in about 1700, England is referred to as a "green and pleasant land", a quote from William Blake's "Jerusalem", written post 1800. And Orlando receives a gift to celebrate the new century from Queen Anne, who in fact had not yet succeeded to the throne.
Potter argued that the more pragmatic medium of cinema called for reasons to drive the narrative, over the novel's abstraction and arbitrariness, especially as the story itself is based on a kind of suspension of disbelief. Thus it is Queen Elizabeth who bestows the long life upon Orlando. The change of sex is a result of Orlando reaching a crisis of masculine identity when he is unwilling to conform to what is expected of him as a man. Nor as a woman can Orlando conform. Unlike the novel, the film ends with Orlando having a daughter, not a son.
Potter also adds: Orlando's words and looks to the camera [were] intended as an equivalent both of Virginia Woolf's direct addresses to her readers and to try to convert Virginia Woolf's literary wit into cinematic humor
The film's last scene takes place in present-day 1992, just as Woolf's novel ends in its present day of 1928.Tilda Swinton as Orlando
Quentin Crisp as Elizabeth I
Jimmy Somerville as Falsetto/Angel
John Wood as Archduke Harry
John Bott as Orlando's father
Elaine Banham as Orlando's mother
Anna Farnworth as Clorinda
Sara Mair-Thomas as Favilla
Anna Healy as Euphrosyne
Dudley Sutton as James I
Simon Russell Beale as Earl of Moray
Matthew Sim as Lord Francis Vere
Charlotte Valandrey as Princess Sasha
Toby Stephens as Othello
Oleg Pogodin as Desdemona
Heathcote Williams as Nick Greene/Publisher
Thom Hoffman as William III
Sarah Crowden as Mary II
Billy Zane as Shelmerdine
Jimmy Somerville – "Eliza Is the Fairest Queen" (Composed by Edward Johnson)
Andrew Watts with Peter Hayward on harpsichord – "Where'er You Walk" (from Semele) (Composed by George Frideric Handel)
Jimmy Somerville – "Coming" (Composed by Sally Potter, Jimmy Somerville, David Motion)
Anonimous - Pavana
Portions of poetry occur in the film:The Faerie Queene by Edmund Spenser
Othello by William Shakespeare
"Sonnet 29" by William Shakespeare
"Women" ("Sūrat an-Nisāʼ") from the Quran
"The Indian Serenade" by Percy Bysshe Shelley
"The Revolt of Islam" by Percy Bysshe Shelley
When first pitching her treatment in 1984, Potter was told the film was "unmakable, impossible, far too expensive and anyway not interesting." Nevertheless, in 1988 she began writing the script and raising money.
Potter saw Tilda Swinton in the Manfred Karge play Man to Man and said that there was a "profound subtlety about the way she took on male body language and handled maleness and femaleness." In Potter's words, Quentin Crisp was the "Queen of Queens . . . particularly in the context of Virginia Woolf's gender-bending politics" and thus fit to play the aged Queen Elizabeth.
Prior to Orlando's release in the United States in June 1993, Vincent Canby wrote an effusively positive review: "This ravishing and witty spectacle invades the mind through eyes that are dazzled without ever being anesthetized. Throughout Ms. Potter's Orlando, as in Woolf's, there [is] a piercing kind of common sense and a joy that, because they are so rare these days in any medium, create their own kind of cinematic suspense and delightedly surprised laughter. Orlando could well become a classic of a very special kind—not mainstream perhaps—but a model for independent film makers who follow their own irrational muses, sometimes to unmourned obscurity, occasionally to glory."
Canby does caution that while the novel stands on its own, he is not yet sure if the film does. Nevertheless, he goes on to comment that "Potter's achievement is in translating to film something of the breadth of Woolf's remarkable range of interests, not only in language and literature, but also in history, nature, weather, animals, the relation of the sexes and the very nature of the sexes."
In contrast, Kenneth Turan of the Los Angeles Times described Orlando as "hollow . . . smug . . . and self-satisfied" and complains that "any kind of emotional connection to match [Orlando's] carefully constructed look . . . is simply not to be had."
By 2010, Orlando was received as part of Potter's successful oeuvre with Matthew Connelly and had one critic affirming in the very first line of his review that "[r]arely have source material, director, and leading actress been more in alignment than in Orlando, the 1992 adaptation of Virginia Woolf's novel, directed by Sally Potter and starring Tilda Swinton [. . .]. Watching Orlando some 17 years after its U. S. theatrical run, however, proves a welcome reminder of just how skillfully they [Potter and Swinton] marshaled their respective gifts here, how openly they entered into a dialogue with Woolf's playful, slippery text."
Rotten Tomatoes scored the film positively at 83% based on 51 reviews.
Orlando was nominated for Academy Awards for art direction (Ben Van Os, Jan Roelfs) and costume design. The film was also nominated for the 1994 Independent Spirit Awards' Best Foreign Film award. At the 29th Guldbagge Awards the film was nominated for the Best Foreign Film award.