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The Shakespeare in Fiction Romantic Comedy that somehow won Best Picture of 1998 at the Academy Awards, surprising all those who were backing Saving Private Ryan. Often cited nowadays as an Award Snub in action.

Meet William Shakespeare (Joseph Fiennes), aspiring playwright who can't find the inspiration to write another Screwball Comedy, and works for a theater that needs money, badly. In the bed of his mistress, Rosaline, he tries to find inspiration for a comedy titled Romeo and Ethel the Pirate's Daughter. Meanwhile, Viola De Lesseps (Gwyneth Paltrow), a noblewoman engaged to marry an entrepreneur in the Americas, dreams of the stage but is frustrated, because women are banned from the boards. However, she goes out to audition anyway, dressed up as a boy, and is astounded when she gets the part... of Romeo. Tension soon erupts between her and the suddenly single Will, and Hilarity, Angst, Secrecy, and a Little Sex Ensue. Much like a Shakespeare comedy, you might say.

Tropes used in Shakespeare in Love include:
  • Aristocrats Are Evil: Viola's husband is a total scumbag. Queen Elizabeth, on the other hand, is hard but fair.
  • Bittersweet Ending: While Shakespeare and Viola didn´t end together, both seem very optimistic about their respective fates. The film ends with Shakespeare writing Twelfth Night.
  • Casting Gag: Ben Affleck has a minor role, playing a big-name actor who is tricked into taking a minor role.
  • Catch Phrase: "I don't know... it's a mystery."
  • Coitus Uninterruptus
  • Deus Ex Machina: Queen Elizabeth I. Of course, there wasn't as much of a stigma attached to the trope back in Shakespeare's day so it's almost justified.
  • Did Not Do the Research: Theater drama did not work the way the movie portrayed. There weren't auditions and casting calls and such. Plays were performed by theater troupes that always acted together, and in fact had to be registered with the government.
  • With a few possible exceptions, Shakespeare didn't write original stories, but instead adapted his plays from older stories or historical sources. Romeo and Juliet was not an original story, and it certainly wasn't reworked from a comedy.
  • Did Not Get the Girl: You should know this already.
  • Driver of a Black Cab: Rower of A Thames Ferry Boat.
Cquote1

 "I had Christopher Marlowe in my boat once."

Cquote2
  • Fake Brit: The Australian Geoffrey Rush, American Ben Affleck and American Gwyneth Paltrow, among others.
  • Follow That Boat!
  • Freud Was Right: When Will is talking to his therapist physician (or something), saying that his inspiration is coming along difficultly, like trying to open a keyhole with a floppy fish...
  • Gondor Calls for Aid:
Cquote1

 "The Master of the Revels despises us all for vagrants and peddlers of bombast. But my father, James Burbage, had the first license to make a company of players from Her Majesty; and he drew from poets the literature of the age. We must show them that we are men of parts. Will Shakespeare has a play. I have a theater. The Curtain is yours."

Cquote2
Cquote1

 Will: "It's as if my quill is broken, as if the organ of my imagination has dried up, as if the proud tower of genius is collapsed. Nothing comes. It's like trying to pick a lock with a wet herring."

Dr. Moth: Tell me, are you lately humbled in the act of love? How long has it been?

Will: A goodly length, in times past, but, lately...

Cquote2
  • Loan Shark: The movie opens with Fennyman the Moneylender torturing the owner of the Rose for his unpaid debts. He ends up being enamoured of the theatre.
  • Mood Whiplash: A few examples:
    • One minute, the troupe is carousing in a local bar/brothel, the next, Henslowe mentions Shakespeare's wife in passing, and Viola takes off. Then one of the actors comes in with the news that Marlowe has been killed, and Shakespeare thinks he's responsible because he gave Wessex Marlowe's name as a pseudonym, and told him that he's been visiting his future wife.
    • After Shakespeare explains how Romeo and Juliet takes a turn for the worse:
Cquote1

 HENSLOWE: *deadpan* Well, that'll have 'em rolling in the aisles.

Cquote2
    • Another example comes after Tilney closes the Rose because they were unknowingly letting Viola act. Fennyman comes in, still wrapped up in trying to memorize his lines, and asks "Everything all right?"
  • The Muse
  • My God, What Have I Done?: Shakespeare, when he thinks he got Marlowe killed by Wessex.
  • Oh Crap: Romeo and Juliet, debut performance. At stake, Shakespeare's entire reputation. Will, playing Romeo, is in the depths of despair; Sam, the boy supposed to play Juliet, has just hit puberty with a horrifically broken voice; and as the curtain rises, the actor reciting the Prologue can't get out a single word in his stuttering panic. The fifteen or twenty seconds that follows is one drawn-out Oh Crap moment before he starts off what has to be the most touching version of Romeo and Juliet ever to be performed onscreen.
  • One-Scene Wonder: Judi Dench as Queen Elizabeth I. Eight minutes of screentime total, and one Oscar for Best Supporting Actress.
  • Oscar Bait
  • Pimped-Out Dress: It's Elizabethan days. What do you expect? It's actually in the script that Viola's dress be literally stunning.
  • Playing Against Type: Colin Firth in a period romantic comedy... as the Prince Charmless whom you don't want the heroine to end up with.
  • Real Life Relative: Husband and wife team of Jim Carter (Ralph Bashford) and Imelda Staunton (Nurse).
  • Recursive Crossdressing
  • The Renaissance
  • Rich Suitor, Poor Suitor: Struggling playwright Shakespeare vs. rich Lord Wessex
  • Romantic Comedy
  • Shakespeare in Fiction: Here, he's young, charismatic, melancholy, mostly lovelorn, and looking for a muse.
  • Shaped Like Itself: "That woman is a woman!"
  • Shown Their Work
  • Slow Clap
  • Star-Making Role: If you didn't know about Gwyneth Paltrow before, you did after it came out.
  • Stuttering Into Eloquence : Wabash, introducing the play.
  • Sweet Polly Oliver
  • Virgin Vision: The Queen has it, unfortunately.
  • Wholesome Crossdresser: Viola and Sam, the actor who is cast as Juliet.
  • Writer's Block Montage: Played with. Our first shot of Will sees him busily and confidently scribbling away, and we cut to his paper to see that he's just trying out different signatures over and over. However, he does crumple up a sheet of parchment and toss it away moodily - only for it to land next to a very Hamlet-esque skull.
    • That in-joke, by the way, is that there are six existent copies of Shakespeare's signature, which vary wildly in spelling and handwriting.
  • Take That: Fennyman proposes to Henslowe that the actors get paid for the play from the nonexistent profits the company will receive, a swipe at Hollywood's rather loose accounting procedures.
  • Young Future Famous People
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