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A 1992 film, written and directed by Sally Potter, based on the novel by Virginia Woolf, and chiefly notable for being the movie which made Tilda Swinton into a star.

The film is set between the Elizabethan era and the present day, and follows the career of the title character, played by Swinton, who starts out as a handsome and somewhat androgynous young nobleman. Orlando's beauty gets the attention of the elderly Elizabeth I, who grants him a big house and lots of land on the condition that he doesn't grow old...which Orlando proceeds not to do. He is, however, unlucky in love, falling for a Russian princess who jilts him. By the 17th century, Orlando is as young as ever and is interested in becoming a writer. He shows his verse to cynical poet Nick Greene, who in return suggests that if only Orlando were to set him up with a financial stipend, he could devote himself to being a full-time writer. Greene reads Orlando's poetry and finds it terrible, and publishes a poem ridiculing Orlando. Orlando is humiliated, but tells his people to pay Greene the stipend anyway.

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By the 18th century, Orlando is a diplomat who has travelled to Constantinople as the English ambassador. While he's there, he gets caught up in a battle. The next morning, he wakes up in his bed to discover that he's turned into a woman, and is fine with that. Orlando travels back to England to find that her new sex raises a lot of questions about who's going to inherit the house if she's not married, because obviously, she can't; she is also now patronised by the intelligentsia. The film moves on to the 19th century, when a dashing American chap named Shelmerdine (Billy Zane) falls off his horse on Orlando's lawn, breaking his ankle. She takes him in and cares for him, and has her first (and only) satisfying love affair.

We see Orlando as a pregnant nurse, stumbling across a World War One battlefield, and then in the present day, Orlando is a single mother and author, shopping the manuscript of her life story to a publisher (played by the same actor who played Nick Greene). He's interested, this time.

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Since the most famous thing about this film is that its title character changes sex, spoilers are unmarked!


Tropes in this film:

  • The Ace: Shelmerdine.
  • Aside Glance: Orlando does a lot of these, most amusingly at the end:
    Publisher: It's really very good. Written from the heart. I think it'll sell. Provided you rewrite it. You know, increase the love interest. Give it a happy ending. By the way, how long did this draft take you?
    Orlando: [Aside Glance]
  • Bifauxnen: Orlando at the end of the film, in her boots, jodhpurs, waistcoat and shirt; she has a ponytail but she holds herself very upright.
  • Bittersweet Ending: Orlando has outlived everyone she's ever loved except for her daughter, and she's lost everything she ever had, but she's got a daughter, a motorbike, a potentially a saleable manuscript, and the knowledge that she represents a possible future for the human race.
    I am coming, I am coming, I am coming through
    Coming across the divide to you
    In this moment of unity
    Feeling an ecstasy
    To be here, to be now
    At last I am free.
    Yes at last, at last, to be free of the past
    and of the future that beckons me
    Yes at last, at last, to be free of the past
    and of the future that beckons me.
    I am coming.
    I am coming.
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  • Breaking Bad News Gently: Orlando turns down the Archduke's hand in marriage this way.
    Archduke: I can offer you a house to rival your own.
    Orlando: [genuinely puzzled] I don't quite understand.
    Archduke: Orlando, to me, you were and always will be, whether male or female...the pink, the pearl, and the perfection of yourself. I'm offering you my hand.
    Orlando: [amazed] Oh. Archduke. [warmly] That is very kind of you, yes. I can't accept.
    Archduke: But I...I, am England. And you are mine.
    Orlando: [nodding] I see. On what grounds?
    Archduke: That I adore you.
    Orlando: And this means that...I belong to you?
    Archduke: Are you refusing me?
    Orlando: [sweetly] I am, I'm sorry.
  • Breaking the Fourth Wall: Orlando does this after changing sex and again in the film's final shot.
  • Can't Hold His Liquor: Downplayed with Orlando, who when exchanging toasts with The Khan in the blazing sun, manages to last for about three drinks before sinking to his knees.
  • Character Development: Male!Orlando tells Princess Sasha "You're mine", and when she asks why, he replies "Because I adore you." A couple of hundred years later, the Archduke uses the same line on Female!Orlando, but this time, she doesn't buy it.
  • Chivalrous Pervert: Male!Orlando in the 1500s, who's engaged to a nice girl but who falls for a Russian princess.
  • Crosscast Role: Orlando himself, at least until the physical transition. Elizabeth I is additionally played by trans woman author, raconteuse and LGBT icon Quentin Crisp, who at the time was unaware of being transgender and was cast as a male actor.
  • The Cynic: Nick Greene, who wants Orlando's patronage but sees no reason why he should even pretend to be grateful for it. Orlando seems to agree.
  • Dissonant Serenity: After a lifetime of disappointments, humiliations, abandonments, her inheritance long since taken away, and everyone she has ever been fond of (except for her daughter) dying on her, the final shot of the film is Orlando smiling mysteriously into the camera with an unblinking stare for twenty-two seconds. Strangely uplifting, because who wouldn't want Tilda Swinton smiling at them for 22 seconds.
  • Even the Guys Want Him: Strongly implied to be the case with Male!Orlando.
  • Fiery Redhead: Inverted. Orlando has red hair but is generally very calm and seldom gets angry or upset.
  • Gender Bender: Orlando changes from a man to a woman halfway through the film.
  • Immortality Begins at 20: It does for Orlando, anyway, who over the course of 400 calendar years, ages by about ten years (Tilda Swinton was 31 when the film was made.)
  • Mars-and-Venus Gender Contrast: By the 1700s Orlando has come to believe this:
    The Khan: [proposing a toast] To beauty of nature. And of course to the beauty of women, and the joys of love.
    [Orlando, who is a bit drunk, sinks to his knees with a pained expression on his face]
    The Khan: I see. You're here as a casualty of love, my friend.
    Orlando: ...They're not like us fellows.
  • Meet Cute: Orlando and Shelmerdine:
    Orlando: [Churning romantic music; Orlando is running through the grounds of her house, in fog; she falls over and lies on the grass] Nature, nature, I'm your bride. Take me.
    [Shelmerdine rides up on his horse and looks down at her. The horse rears, he falls off next to her. Orlando does an Aside Glance and stares at him.]
    Shelmerdine: You're hurt, ma'am?
    Orlando: [awestruck by his handsomeness] I'm dead, sir.
    Shelmerdine: Dead. That's serious. Can I help?
    Orlando: ...Will you marry me?
    Shelmerdine: Ma'am... I would gladly... um, I...but I fear my ankle is twisted.
    [Cut to Orlando on horseback with him behind her, cantering back to the house]
  • Ms. Fanservice: When female Orlando looks at herself in the mirror after the transformation.
  • Pretty Boy: Orlando is a youthful pretty boy in the first half of the film, accentuated by his fashionably long hair (and underlined by the fact that he's played by Tilda Swinton).
  • The Reveal: The mirror scene. Orlando wakes up in wig and shirt and lies there for a moment, staring into space, then takes the wig off and leaves. The shirt falls on the bed. Orlando goes to the washstand, washes face, then pauses, and looks off. Cut to naked Orlando looking at Orlando's reflection in a full-length mirror: she now has a woman's body. She stares at herself for a long moment.
    Orlando: Same person. [smiles] No difference at all. [looks into camera] Just a different sex.
  • Straw Misogynist: Pope. Downplayed in that Pope doesn't actively hate women, he just has zero respect for them. Also Justified, as this is Truth in Television.note 
    Orlando: [who has recently turned into a woman] Gentlemen, I find it strange. You are poets, each one of you, and speak of your muse in the feminine. And yet you appear to feel neither tenderness nor respect towards your wives, nor towards females in general.
    Pope: Madam. I have only the highest regard and purest respect for females.
    Orlando: I find no evidence of that sentiment in your conversation.
    Pope: Conversation is a place where one plays with ideas my dear lady. One forges them quite alone.
    [Murmurs of "Quite" from the other male writers in the room]
    Pope: The intellect is a solitary place, and therefore quite unsuitable a terrain for females, who must discover their natures through the guidance of a father, or husband.
    Orlando: And if she has neither?
    Pope: [patronising smile] Then...however charming she may be, dear lady...she is lost.
  • Stylistic Suck: Orlando's poetry.
  • Tears of Joy: Orlando has these at the end of the film, watching her daughter run through the grass and listening to the angel hovering above the tree singing to her. Coupled with Dissonant Serenity:
    Daughter: Why are you sad?
    Orlando: I'm not. I'm happy. Look up there.
  • Unfazed Everyperson: The weird things that happen to Orlando (never getting old, changing from man to woman) never startle or surprise him/her; he/she only gets upset when someone dumps, insults, harries or otherwise mistreats him/her.
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