Orlando: A Biography is a fictional biography by Virginia Woolf. The novel follows Orlando, who starts out as a young nobleman during the reign of Queen Elizabeth I, and follows his love affair with a Russian princess, his ambassadorship in the East, and his spontaneous sex-change and life afterward as a woman. Despite living from the 16th through the 20th centuries, Orlando is 36 when the novel ends in the present day (well, October 11, 1928, but that was the present when it was written). The various themes of the novel, including gender, literature and poetry, and the passage of time, are explored by Orlando's experiences with these subjects.
Being mainly known for being a story of gender-bending, Orlando covers many Gender Blending Tropes. The novel was partly written by Woolf as a love letter to her then-partner, Vita Sackville-West.
Orlando was made into a movie starring Tilda Swinton in 1992, and adapted into a play by Sarah Ruhl in 2010. Notably, the character is also featured prominently in Alan Moore's The League of Extraordinary Gentlemen.
Orlando: A Biography contains examples of following tropes:
- Abhorrent Admirer: Archduke Harry
- Anthropomorphic Personifications: Purity, Chastity, and Modesty. See the entry for Big-Lipped Alligator Moment on the YMMV page.
- Asleep for Days: Orlando is asleep for a week after the disastrous end to his affair with the Russian princess, and again before his change into a woman.
- Attractive Bent-Gender: Orlando was already good-looking as a man; upon transformation, Lady Orlando's body is said to have the best-looking aspects of either gender.
- Engaging Conversation: Orlando gets engaged to Bonthrop a few minutes after they meet.
- Gender Bender: One of the earliest in literature; anything older is usually covered by mythology instead, like Tiresias of Greek Mythology.
- Getting Crap Past the Radar: Depictions of bisexuality in fiction were illegal in Britain at the time, so Woolf gets around this by having her character switch sexes midway through the novel.
- Hide Your Gays: Archduke Harry originally tries to woo the male Orlando disguised as a woman, but drops the disguise after Orlando becomes a woman.
- Humble Goal: Bonthrop's main desire in life is to sail around Cape Horn, again and again and again. He often shipwrecks and survives—he's another one of those people who lives for centuries.
- Jumping the Gender Barrier: Orlando is a playboy only interested in women when he is a man, and then shows only interest in men when he becomes a woman.
- Well, there were Nell and her friends, whom Orlando remembers quite fondly afterwards (though she might not have sex with any of them, she clearly was attracted to Nell). And though she managed to convince "spirit of the age" that it's okay for a woman to compare flowers to Egyptian girls in her poetry as long as she has a husband, a narrator notices that "she had only escaped by the skin of her teeth" there.
- Just Woke Up That Way: How Orlando turned into a woman.
- Leaning on the Fourth Wall: Orlando is sensitive to the fact that that it's the "present day" according to her "biographer".
- Lemony Narrator: The narrator gets bored, goes off on tangents, complains about the missing evidence, knows things he shouldn't, doesn't know things he should...
- Man, I Feel Like a Woman: Subverted
- Mother Russia Makes You Strong: Discussed with Sasha.
- Overly Long Name: Seems to be common with people Orlando is romantically linked with
- Princess Maroucha Stanilovska Dagmar Natasha Iliana Romanovitch
- Lady Margaret O'Brien O'Dare O'Reilly Tyrconnel
- Marmaduke Bonthrop Shelmerdine, Esquire
- True Art Is Ancient: An In-Universe example. To Nicholas Green, who also lives for centuries longer than he should, the greatest art is always that of about five hundred years ago.
- Second Law of Gender Bending: Succinctly summarized by the protagonist:Orlando: Praise god I'm a woman!
- (S)he's Got Legs: The narrator frequently comments on the shapeliness of Orlando's legs and all the characters checking them out; and, in a slight inversion, does it much more often for Male!Orlando than Female!Orlando.
- Speculative Fiction LGBT: Orlando begins as a heterosexual male in the early 20th Century, and through time travel accidentally swaps gender, but never has to define or justify their existence. Though the concept of gender is wholly linked to biological sex, it is an early example of using the genre to discuss very untouched issues, and may be opening a discourse on being transgender.
- Unusually Uninteresting Sight: Everyone treats Orlando's eternal youth and gender changes as totally unremarkable, including Orlando him/herself.
- Victoria's Secret Compartment: Over the years, Orlando keeps her manuscript of "The Oak Tree" in her bosom. Probably in more of a secluded pocket than right next to her skin, but still...