The tale unfolds in the Elizabethan era, specifically in 1600 AD, just before the passing of Queen Elizabeth I (Quentin Crisp) in 1603. On her deathbed, the queen grants an androgynous young nobleman named Orlando (Tilda Swinton) a substantial tract of land and a castle, along with a generous monetary gift. However, this is contingent upon an unusual command: “Do not fade. Do not wither. Do not grow old.” Queen Elizabeth cherished Orlando as the son of her later years, regarding him with fondness.
Following Elizabeth's death, Orlando finds himself captivated by Sasha ([Charlotte Valandrey]), the daughter of a Russian diplomat, in 1610, while he is engaged to an English noblewoman. The Earl of Moray ([Simon Russell Beale]) cautions Orlando about the potential fallout from this liaison. Despite the warning, Orlando chooses love over duty, thus ending his engagement. However, his joy is shattered when he sees Sasha sharing a kiss with a Russian sailor. Although Sasha insists it was merely a misunderstanding, Orlando is heartbroken when she decides to leave once the ice melts.
By 1650, Orlando decides to retreat into solitude in the castle, sleeping for an entire week and spending centuries immersed in poetry and art. He seeks validation for his work from prominent poets like Nick Greene ([Heathcote Williams]), who scorns his efforts. Despite trying to cultivate a friendship, Orlando learns a harsh lesson about the art world and sends Greene away after realizing the disdain hidden behind Greene's mirth.
In 1700, Orlando embarks on a new chapter as the English ambassador to the Ottoman Empire, where he forms a close bond with The Khan ([Lothaire Bluteau]), the emperor, over shared meals and camaraderie. However, the arrival of Archduke Harry ([John Wood]) marks both promotion and turmoil. Amid escalating tensions and the threat of war, Orlando is thrust into battle, where the brutality of conflict leaves a deep impression on him.
After a week of unconsciousness following the war, Orlando awakens to a shocking revelation: he has transformed into a woman. Now identified as Lady Orlando, she returns to her estate in 1750, dressed in Middle Eastern garb, only to discover looming lawsuits claiming her inheritance on the basis that she is a woman and thus ineligible. Although Archduke Harry offers marriage for respectability, Orlando rebuffs him, leading to indignation.
Orlando's journey continues as she embraces her passion for poetry, crossing paths with influential writers like Swift ([Roger Hammond]) and Pope ([Peter Eyre]). She recognizes that while they draw inspiration from women, their opinions reflect a profound disrespect for the female experience, regarding women without male guardianship as “lost.”
Over the ensuing centuries, Orlando's heart finds new love in an American adventurer named Shelmerdine ([Billy Zane]). She believes she has finally met her soulmate, yet political demands complicate her life as the British crown declares her a female who must produce an heir to retain her estate. Torn between love and obligation, Orlando chooses to remain, refusing Shelmerdine’s invitation to the land of liberty and freedom.
Ultimately, the journey of love, loss, marriages, and the weight of history unfolds, leading into the early 1990s, where Orlando, now a mother, is in search of a publisher for her work. A literary editor, played by Heathcote Williams, acknowledges her efforts as “quite good,” marking a significant moment in her literary pursuit. Reflecting on her extraordinary life, Orlando, now relaxing with her daughter, simply points out an angel in the sky, embodying the surreal beauty of her existence.
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