''Orlando: A Biography'' is a fictional biography by Creator/VirginiaWoolf. 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 [[GenderBender 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 GenderBlendingTropes. The novel was supposedly written by Woolf as a love letter to her lesbian lover Vita Sackville-West.
''Orlando'' was made into a movie starring TildaSwinton in 1992, and adapted into a play by Sarah Ruhl in 2010. Notably, the character is also featured prominently in Creator/AlanMoore's ''ComicBook/TheLeagueOfExtraordinaryGentlemen''.
!!''Orlando: A Biography'' contains examples of following tropes:
* AbhorrentAdmirer: Archduke Harry
* AnthropomorphicPersonifications: Purity, Chastity, and Modesty. See the entry for BigLippedAlligatorMoment on the YMMV page.
* AttractiveBentGender: 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.
* GenderBender: One of the earliest in literature; anything older is usually covered by mythology instead, like Tiresias of GreekMythology.
* GettingCrapPastTheRadar: Depictions of [[NoBisexuals 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.
* HideYourGays: Archduke Harry originally tries to woo the male Orlando disguised as a woman, but drops the disguise after Orlando becomes a woman.
* JumpingTheGenderBarrier: 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 [[HookerWithAHeartOfGold 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.
* JustWokeUpThatWay: How Orlando turned into a woman.
* LemonyNarrator: The narrator gets bored, goes off on tangents, complains about the missing evidence, knows things he shouldn't, doesn't know things he should...
* ManIFeelLikeAWoman: Subverted
* MotherRussiaMakesYouStrong: Discussed with Sasha.
* TrueArtIsAncient: An InUniverse example. To Nicholas Green, [[spoiler: who also lives for centuries longer than he should]], the greatest art is always that of about five hundred years ago.
* SecondLawOfGenderBending: Succinctly summarized by the protagonist:
-->'''Orlando''': Praise god I'm a woman!
* UnusuallyUninterestingSight: Everyone treats Orlando's eternal youth and gender changes as totally unremarkable, including Orlando him/herself.
* VictoriasSecretCompartment: 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''...