Orlando (1992)

The story begins in the Elizabethan era, shortly before the death of Queen Elizabeth I in 1603. On her deathbed, the Queen promises an androgynous young nobleman named Orlando a large tract of land and a castle built on it, along with a generous monetary gift; both Orlando and his heirs would keep the land and inheritance forever, but Elizabeth will bequeath it to him only if he assents to an unusual command: "Do not fade. Do not wither. Do not grow old." Orlando acquiesces and reposes 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 Ottoman Empire, and is almost killed in a diplomatic fracas. Waking up the next morning, he learns something startling: he has transformed into a woman.The now Lady Orlando comes home to her estate in Middle-Eastern attire, only to learn that she faces several impending lawsuits arguing that Orlando was a woman all along and therefore has no right to the land or any of the royal inheritance that the Queen had promised. The succeeding two centuries tire Orlando out; the court case, bad luck in love, and the wars of British history eventually bring the story to the present day (i.e., the early 1990s). Orlando now has a young daughter in tow and is in search of a publisher for her book. (The literary editor who judges the work as "quite good" is portrayed by Heathcote Williams?the same actor who played the poet who had, earlier in the film, denigrated Orlando's poetry.) Having lived a most bizarre existence, Orlando, relaxing with her daughter and daydreaming philosophically under a tree, has finally found a tranquil niche.