Orlando

As the Elizabethan era draws to a close in 1600 AD, Queen Elizabeth I (Quentin Crisp) lies on her deathbed, her thoughts consumed by the young nobleman Orlando (Tilda Swinton), an androgynous individual she has come to regard as a surrogate son. In her final moments, she bestows upon him a grand inheritance: a vast tract of land and a majestic castle built upon it, accompanied by a substantial monetary gift. However, this generosity comes with a peculiar condition: Orlando must swear to remain forever young, vibrant, and ageless. The queen's affection for Orlando is palpable, as he has served as her confidant and companion throughout the years.

Following Elizabeth's passing in 1603, Orlando finds himself entwined in a complex web of emotions when he becomes smitten with Sasha (Charlotte Valandrey), the ravishing daughter of a Russian diplomat, in 1610. Despite being engaged to an English noblewoman at the time, Orlando's heart belongs to Sasha. Earl of Moray's (Simon Russell Beale) warning that his affair with Sasha will be perceived as a slight against all English women only serves to fuel Orlando's passion. The couple's romance is eventually thwarted when Sasha is caught kissing a Russian sailor, and she decides to abandon Orlando once the ice melts.

Crushed by heartbreak, Orlando retreats to his castle, where he devotes centuries to honing his artistic skills, producing exquisite poetry and art. However, his efforts at validation are met with ridicule from celebrated poets like Nick Greene (Heathcote Williams), who scoffs at Orlando's work. Despite offering Greene a pension of 300 pounds per year, the poet remains unimpressed, implying that he dare not offend Orlando due to his vast wealth. Orlando, however, recognizes Greene's true nature and banishes him from the castle, forevermore reposing in splendid isolation, his artistic pursuits a testament to the enduring power of beauty and creativity.

In 1700, Orlando ventures to Constantinople as England's ambassador to the Ottoman Empire, where he forges an enduring bond with Emperor The Khan (Lothaire Bluteau). Ten years pass, and Archduke Harry (John Wood) arrives, bearing the news that Queen Anne has elevated Orlando in her royal court. As they celebrate, the Emperor reveals that their enemies are at the gates, and Orlando is compelled to honor his promise by taking up arms alongside the Ottoman forces. Witnessing the horrors of war firsthand, Orlando falls unconscious.

Seven days later, he awakens to a startling reality: he has transformed into a woman. Lady Orlando returns to her estate in Middle Eastern attire, only to discover that she faces numerous lawsuits questioning her very identity and right to the land and royal inheritance promised by Queen Anne. Archduke Harry offers his hand in marriage, promising respectability, but Orlando refuses, offending Harry.

As Lady Orlando navigates this new reality, she finds solace in poetry, befriending leading authors like Swift (Roger Hammond) and Pope (Peter Eyre). However, she soon realizes that women are often regarded as mere muses, lacking the respect and admiration they deserve. The societal norms of her time dictate that a woman without a father or husband is considered "lost."

The weight of two centuries bears down upon Orlando, who finds herself torn between her love for poetry and her desire for true connection. She falls deeply in love with US adventurer Shelmerdine (Billy Zane), feeling as though she has finally found her soulmate. Despite the strong chemistry between them, Orlando's concerns about losing her property and legacy keep her from following Shelmerdine to the United States.

As the British crown pronounces its judgment on Orlando, she is faced with an impossible choice: conform to societal expectations or risk everything for love and freedom. The court case, a series of unfortunate events, and the tumultuous backdrop of British history eventually bring the story full circle, arriving in the early 1990s.

Now, Orlando is accompanied by her young daughter as she searches for a publisher willing to take a chance on her literary work. A literary editor (Heathcote Williams), who had earlier dismissed Orlando's poetry, offers his critique, pronouncing it "quite good."

As she basks in the warm glow of domesticity, surrounded by the comforting familiarity of maternal love, Orlando's gaze drifts away from the gentle rhythms of conversation and settles on a figure that defies explanation. With an air of quiet authority, she beckons her daughter to join her in beholding this ethereal visitor, its presence imbuing the room with an otherworldly essence that seems to hover just beyond the fringes of reality. As mother and child lock eyes on this celestial stranger, a sense of wonder and trepidation mingles in their shared awareness, like the whispers of secrets shared between old friends.