Orlando: A Biography is an influential novel by Virginia Woolf, first published on 11 October 1928. A semi-biographical novel based in part on the life of Woolf's lover Vita Sackville-West, it is generally considered one of Woolf's most accessible novels. The novel has been influential stylistically, and is considered important in literature generally, and particularly in the history of women's writing and gender studies. A film adaptation was released in 1992, starring Tilda Swinton as Orlando and Quentin Crisp as Queen Elizabeth I.

Plot
Orlando tells the story of a young man named Orlando, born in England during the reign of Elizabeth I, who decides not to grow old. He is briefly a lover to the decrepit queen, but after her death has a brief, intense love affair with Sasha, a princess in the entourage of the Russian embassy. This episode, of love and excitement against the background of the Great Frost, is one of the best known, and is said to represent Vita Sackville-West's affair with Violet Trefusis.

Following Sasha's sudden, unwarned departure and return to Russia, the desolate, heartbroken Orlando returns to writing The Oak Tree, a poem started and abandoned in his youth. He meets with Nicholas Greene, a famous poet and wit whom he joyfully entertains, but who criticises Orlando's writing, later making Orlando feel betrayed when he finds himself made the foolishly-depicted subject of one of Greene's subsequent works. This period of contemplating love and life leads Orlando to appreciate the value of his ancestral stately home, which he proceeds to furnish lavishly and then plays host to the populace. Ennui sets in and the harassment of a persistent suitor, the Archduchess Harriet, leads to Orlando's fleeing the country when appointed by King Charles II as British ambassador to Constantinople. Orlando performs his duties well, until a night of civil unrest and murderous riots. He falls asleep for a lengthy period of days while in Turkey, resistant to all efforts to rouse him. Upon awakening he finds, unsurprised, that he has metamorphosed into a woman—the same person, with the same personality and intellect, but in a woman's body.

The now Lady Orlando covertly escapes Constantinople in the company of a Gypsy clan, adopting their way of life until its essential conflict with her upbringing leads her to head home. Only on the ship back to England, with her constraining female clothes and an incident in which a flash of her ankle nearly results in a sailor's falling to his death, does she realise the magnitude of becoming a woman; yet she concludes the overall advantages, declaring 'Praise God I'm a woman!' Back in England, Orlando is hounded once again by the archduchess, who now reveals herself in fact to be a man, the Archduke Harry. Orlando evades his marriage proposals, instead living a life switching between gender roles, dressing as both man and woman.

Orlando soon becomes caught up in the life of the eighteenth and nineteenth centuries, holding court with the great poets (notably Alexander Pope), including Nick Greene who appears to be as timeless as she, now promoting her writing and promising to help her publish The Oak Tree. Orlando wins a lawsuit over her property and marries a sea captain, Marmaduke Bonthrop Shelmerdine. In 1928, she publishes The Oak Tree centuries after starting it, winning a prize. As her husband's ship returns, in the aftermath of her success, she rushes to greet him.

Apart from being, at the beginning of the book, a knightly young man, ready for adventure, Woolf's character takes little from the legendary hero Orlando of the Italian Renaissance, spoken by Ludovico Ariosto in the Orlando Furioso.

Orlando can be read as a roman à clef: the characters Orlando and Princess Sasha in the novel refer to Vita Sackville-West and Violet Trefusis respectively. The photographs printed in the illustrated editions of the text are all of the real Vita Sackville-West. Her husband, Harold Nicolson, appears in the novel as Marmaduke Bonthrop Shelmerdine. "The Oak Tree", the poem written by Orlando in the novel, refers to the poem "The Land", for which Vita had won the Hawthornden Prize in 1926. Moreover, the minor character Nick Greene, who later reappears as Sir Nicholas Greene, spouts opinions which had been uttered in real life by Logan Pearsall Smith.[1]

For historical details Woolf draws extensively from Knole and the Sackvilles, a book written (and reworked in several versions) by Sackville-West, describing the historic backgrounds of her ancestral home, Knole House in Kent. Other historical details derive from John Dryden's Essay of Dramatick Poesie. (Orlando, personified as one of Vita's ancestors — the 6th Earl of Dorset — discusses artistic topics with his contemporaries as described in that book.) Orlando is also an attractive version of a history book on the Sackvilles' noble descendants, their estates, their culture, etc; Woolf was middle-class and fascinated by the aristocracy, as embodied in Vita. (Vita also wrote about these subjects, but Woolf thought Vita had a "pen of brass").

The conventions of fiction and fantasy (e.g., fictional names and a main character who lives through many centuries) allowed Woolf to write a well-documented biography of a person living in her own age, without opening herself to criticism about controversial topics such as lesbian love. While Orlando was published in the same year as The Well of Loneliness, a novel banned in the UK for its lesbian theme, it escaped censorship because the main character appears as a man when he loves Princess Sasha.

Vita's mother, Lady Sackville, was not pleased at the writing of the novel, because she believed the story was too plain in its meaning, and she would call Woolf the "virgin wolf" henceforth. Violet Trefusis's reply would be a more conventional roman à clef (Broderie Anglaise), which loses much of its interest if the reader does not know the background, whereas Orlando remains a captivating novel, even if the reader does not know the identity of the person in the photographs in the book.

Orlando: A Biography was described as an elaborate love letter from Virginia Woolf to Vita Sackville-West (by the latter's son Nigel Nicolson); nonetheless, Woolf intended her novel as the first in a new trend, breaking the boundaries between what are traditionally seen as the fiction and non-fiction genres in literature (so the novel is not only about trans-gender, but also trans-genre, so to speak).[citation needed] This was not to be, however, as the book is invariably called a "novel" (while Woolf called it a "biography"), and is shelved in the "fiction" section of libraries and bookshops. Only in the last decades of the 20th century would authors again try this "tricky" cross-over genre (which differs from "romanticised" or "popularised" non-fiction, and does not necessarily have to take a roman à clef form) , e.g., Flaubert's Parrot by Julian Barnes (ISBN 0-330-28976-4).

Influence and recognition
The work has been the subject of numerous scholarly writings, including detailed treatment in multiple works on Virginia Woolf.[2] An "annotated" edition has been published to facilitate critical reading of the text.

The novel's title has also come to stand for women's writing generally in some senses, as one of the most famous works by a woman author very directly treating gender.[3] For example, a project on the history of women's writing in the British Isles was named after the book.[4]