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1[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/orlando_movie.png]]
2
3A 1992 film, written and directed by Sally Potter, based on the novel by Creator/VirginiaWoolf, and chiefly notable for being the movie which made Creator/TildaSwinton into a star.
4
5The 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 UsefulNotes/ElizabethI, 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.
6
7By 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 (Creator/BillyZane) 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.
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9We 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.
10
11Since the most famous thing about this film is that its title character changes sex, '''spoilers are unmarked'''!
12
13----
14!!Tropes in this film:
15* TheAce: Shelmerdine.
16* AsideGlance: Orlando does a lot of these, most amusingly at the end:
17-->'''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?
18-->'''Orlando''': [''AsideGlance'']
19* AwkwardPoetryReading: The movie kicks off with the eponymous young nobleman performing "The Bower Of Bliss" before the visiting Queen Elizabeth I. It's a little stilted at first and made a tad strange by Orlando's rather evocative gestures, but it doesn't ''really'' become awkward until he reaches the bit about how the virgin rose "fades and falls away"... whereupon a distinctly miffed Elizabeth points out that the poem isn't exactly appropriate when addressed by a callow youth to a ''very'' old woman. It's so awkward, Orlando's father has to step in and apologise on his behalf. Elizabeth is able to use the faux pas as an excuse to take the young man as a favourite, eventually leading to her granting Orlando a very generous gift of land - [[OnOneCondition on the condition]] that [[ImmortalityInducer he does not fade or grow old]].
20* {{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.
21* BittersweetEnding: [[spoiler: 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.]]
22-->''I am coming, I am coming, I am coming through''\
23''Coming across the divide to you''\
24''In this moment of unity''\
25''Feeling an ecstasy''\
26''To be here, to be now''\
27''At last I am free.''\
28''Yes at last, at last, to be free of the past''\
29''and of the future that beckons me''\
30''Yes at last, at last, to be free of the past''\
31''and of the future that beckons me.''\
32''I am coming.''\
33''I am coming.''
34* BreakingBadNewsGently: Orlando turns down the Archduke's hand in marriage this way.
35-->'''Archduke''': I can offer you a house to rival your own.
36-->'''Orlando''': [''genuinely puzzled''] I don't quite understand.
37-->'''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.
38-->'''Orlando''': [''amazed''] Oh. Archduke. [''warmly''] That is very kind of you, yes. I can't accept.
39-->'''Archduke''': But I...I, am England. And you are mine.
40-->'''Orlando''': [''nodding''] I see. On what grounds?
41-->'''Archduke''': That I adore you.
42-->'''Orlando''': And this means that...I belong to you?
43-->'''Archduke''': Are you refusing me?
44-->'''Orlando''': [''sweetly''] I am, I'm sorry.
45* BreakingTheFourthWall: Orlando does this a lot.
46* CantHoldHisLiquor: 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.
47* CharacterDevelopment: 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, and being on the recipient end of that love possessiveness, finally understands why it was such an awful idea.
48* ChivalrousPervert: Male!Orlando in the 1500s, who's engaged to a nice girl but who falls for a Russian princess.
49* CrosscastRole: 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 (in fact, Crisp didn't come out until shortly before dying at age 90) and was cast as a male actor.
50* TheCynic: 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.
51* DissonantSerenity: [[spoiler: 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.
52* EvenTheGuysWantHim: Male!Orlando, as we find out after the change, when the Archduke admits that he's been admiring Orlando since well before the change.
53* FieryRedhead: Inverted. Orlando has red hair but is generally very calm and seldom gets angry or upset.
54* GenderBender: Orlando changes from a man to a woman halfway through the film.
55* ImmortalityBeginsAtTwenty: 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.)
56* LivingForeverIsNoBigDeal: Orlando barely even seems to notice their immortality, adapting to the changing eras without being overjoyed, overly depressed, or even mentioning the fact that they're still alive after all these centuries. The nearest Orlando gets to being inescapably miserable because of eternal life is when [[spoiler: she loses her house to a legal catastrophe (being both female and legally dead), Shelmerdine leaves her to pursue freedom, and she's left to struggle alone through war and pregnancy during the early 20th century.]] And she bounces back from ''that'', too!
57* MarsAndVenusGenderContrast: By the 1700s Orlando has come to believe this:
58-->'''The Khan''': [''proposing a toast''] To beauty of nature. And of course to the beauty of women, and the joys of love.\
59[''Orlando, who is a bit drunk, sinks to his knees with a pained expression on his face'']
60-->'''The Khan''': I see. You're here as a casualty of love, my friend.
61-->'''Orlando''': ...They're not like us fellows.
62* MeetCute: Orlando and Shelmerdine:
63-->'''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.\
64[''Shelmerdine rides up on his horse and looks down at her. The horse rears, he falls off next to her. Orlando does an AsideGlance and stares at him.'']
65-->'''Shelmerdine''': You're hurt, ma'am?
66-->'''Orlando''': [''awestruck by his handsomeness''] I'm dead, sir.
67-->'''Shelmerdine''': Dead. That's serious. Can I help?
68-->'''Orlando''': ...Will you marry me?
69-->'''Shelmerdine''': Ma'am... I would gladly... um, I...but I fear my ankle is twisted.\
70[''Cut to Orlando on horseback with him behind her, cantering back to the house'']
71* MsFanservice: When female Orlando looks at herself in the mirror after the transformation.
72* PrettyBoy: 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).
73* TheReveal: 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.
74-->'''Orlando''': Same person. [''smiles''] No difference at all. [''[[BreakingTheFourthWall looks into camera]]''] Just a different sex.
75* StrawMisogynist: Pope. Downplayed in that Pope doesn't actively hate women, he just has zero respect for them. Also Justified, as this is TruthInTelevision.[[note]]cf. Pope's [[http://www.bartleby.com/203/144.html ''Moral Essays'']], Epistle II: Of the Characters of Women[[/note]]
76-->'''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.
77-->'''Pope''': Madam. I have only the highest regard and purest respect for females.
78-->'''Orlando''': I find no evidence of that sentiment in your conversation.
79-->'''Pope''': Conversation is a place where one ''plays'' with ideas my dear lady. One ''forges'' them quite alone.\
80[''Murmurs of "Quite" from the other male writers in the room'']
81-->'''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.
82-->'''Orlando''': And if she has neither?
83-->'''Pope''': [''patronising smile''] Then...however charming she may be, dear lady...she is lost.
84* StylisticSuck: Orlando's poetry.
85* TearsOfJoy: Orlando has these [[spoiler: 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 DissonantSerenity:
86-->'''Daughter''': Why are you sad?
87-->'''Orlando''': I'm not. I'm happy. Look up there.
88* [[UnfazedEveryman 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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