Shakespeare in Love Trivia
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49 free Shakespeare in Love trivia questions with answers — entertainment quiz, new questions added Sep 2026.
This Shakespeare in Love trivia quiz covers John Madden's 1998 romantic comedy from the plot to the Oscar controversy. It starts with the story: Will's writer's block on Romeo and Ethel the Pirate's Daughter, Viola de Lesseps auditioning as Thomas Kent, the £50 wager judged by Queen Elizabeth, Marlowe's death, the boy John Webster and his mice, and the closing image that becomes Twelfth Night. Then it goes behind the scenes to the version that collapsed at Universal in 1991 when Julia Roberts insisted on Daniel Day-Lewis, Tom Stoppard's rewrite of Marc Norman's script, the actresses who turned Viola down and the reshot ending. There is also a round on the 71st Academy Awards, where the film beat Saving Private Ryan for Best Picture, Gwyneth Paltrow beat Cate Blanchett, and Judi Dench won for roughly eight minutes on screen, plus a few questions on the historical liberties the film takes and the Lee Hall stage adaptation. If you want the plays themselves, our Shakespeare quiz covers the real Bard. Every answer here was checked against encyclopaedia entries before publishing.
30 of 49 questions with answers and explanations. Play the quiz
Q 01Who directed Shakespeare in Love?
John Madden
John Madden was hired after the studio passed over Edward Zwick, who had nursed the project for years; Zwick stayed on as a producer and collected a Best Picture Oscar anyway.
Q 02Who plays William Shakespeare in Shakespeare in Love?
Joseph Fiennes
Joseph Fiennes landed the part years after his brother Ralph had screen-tested for it in an earlier version of the film that collapsed before shooting.
Q 03Who plays Viola de Lesseps in Shakespeare in Love?
Gwyneth Paltrow
Gwyneth Paltrow won the Best Actress Oscar for the part, accepting it in a pink Ralph Lauren gown she had picked out herself with no stylist.
Q 04In Shakespeare in Love, theatre owner Henslowe insists audiences want love and a bit with what?
A dog
A dog is Henslowe's formula for a hit, so he is crestfallen when Will's new tragedy turns out to have "no dog of any kind".
Q 05In Shakespeare in Love, what is the working title of Will's stalled comedy?
Romeo and Ethel, the Pirate's Daughter
Romeo and Ethel, the Pirate's Daughter goes nowhere until rival playwright Christopher Marlowe casually hands Will the plot over a drink, feuding families and doomed best friend included.
Q 06Under what male name does Viola audition in Shakespeare in Love?
Thomas Kent
Thomas Kent is her alias, and the Queen later saves the whole company from arrest by declaring Kent merely a man with a remarkable resemblance to a woman.
Q 07Which theatre does Philip Henslowe own in Shakespeare in Love?
The Rose
The Rose was a real Bankside playhouse; when builders uncovered its foundations in 1989, Britain's leading actors linked arms with campaigners to stop the bulldozers.
Q 08Who plays theatre owner Philip Henslowe in Shakespeare in Love?
Geoffrey Rush
Geoffrey Rush plays the debt-ridden impresario, who opens the film with his feet held over hot coals by a moneylender he promptly talks into becoming his partner.
Q 09Who plays Queen Elizabeth I in Shakespeare in Love?
Judi Dench
Judi Dench won an Oscar for the role, and the filmmakers then gave her the film's full-size replica playhouse, which she kept in storage for years hoping to see it rebuilt as a working theatre.
Q 10Accepting her Oscar for Shakespeare in Love, the actress playing Elizabeth I joked she had been on screen for how long?
Eight minutes
Eight minutes was her own count: she told the audience that for so little screen time she should only get a little bit of the statuette, and it remains one of the briefest Oscar-winning turns.
Q 11In Shakespeare in Love, what does Lord Wessex chiefly want from marrying Viola?
Her father's money
Her father's money is the whole bargain: Wessex offers an ancient name to a merchant's grandchildren and, as he tells Viola flatly, gets to recover his fortune in return.
Q 12Who plays Lord Wessex in Shakespeare in Love?
Colin Firth
Colin Firth plays the villain years after reading for the hero: he was one of the actors tried out as Shakespeare for an earlier version of the film that was never made.
Q 13In Shakespeare in Love, Will goads Wessex into a £50 wager while disguised as what?
A chaperone
A chaperone: Will goes to court in a dress as Viola's country cousin and baits Wessex into betting £50, exactly the sum he needs to buy into an acting company.
Q 21In Shakespeare in Love, the Queen tells Will to write something more cheerful next time, for which occasion?
Twelfth Night
Twelfth Night is the commission, and the film ends with Will beginning that very play, whose heroine, named after his lost love, survives a shipwreck and disguises herself as a man.
Q 22In Shakespeare in Love, Viola's disguised audition speech comes from which play?
The Two Gentlemen of Verona
The Two Gentlemen of Verona is the comedy she has just seen at court, so while every other hopeful trots out the same Marlowe speech, she wins Will over with his own words.
Q 23Who first suggested the idea for Shakespeare in Love to screenwriter Marc Norman?
His son
Q 14In Shakespeare in Love, why does Will feel guilty when Marlowe is killed?
He gave Marlowe's name as his own
He gave Marlowe's name as his own when a jealous Wessex confronted him at the ball, so when news of the stabbing arrives Will assumes the revenge fell on the wrong man.
Q 15Who plays Christopher Marlowe in Shakespeare in Love?
Rupert Everett
Rupert Everett plays him as the star Will lives in the shadow of: even the boatman rowing Will across the Thames brags that he once had Marlowe in the back of his boat.
Q 16Which role does Ben Affleck play in Shakespeare in Love?
Ned Alleyn
Ned Alleyn is the vain star actor Will needs, and he only agrees to play the supporting part of Mercutio because Will tells him the play itself is called Mercutio.
Q 17In Shakespeare in Love, the bloodthirsty boy who feeds mice to a cat grows up to be which real playwright?
John Webster
John Webster went on to write The Duchess of Malfi and The White Devil, tragedies notorious for their bloodshed, which is why the film's boy insists that plenty of blood is the only writing.
Q 18In Shakespeare in Love, why does the Master of the Revels finally shut Henslowe's theatre?
A woman has been acting on stage
A woman has been acting on stage: a boy who spied on the lovers tips off the Master of the Revels, who storms into rehearsal and unmasks the company's Romeo.
Q 19In Shakespeare in Love, why does Viola end up playing Juliet on opening day?
The boy actor's voice breaks
The boy actor's voice breaks just before the performance, and Viola, who already knows the play by heart, steps in to play Juliet opposite Will's Romeo.
Q 20In Shakespeare in Love, where does the Queen order Viola to sail with Wessex?
Virginia
Virginia is an anachronism: the film is set in 1593, and Jamestown, the first lasting English settlement there, was not founded until 1607.
His son Zach sold him on showing Shakespeare as a young man; Norman could not crack it at first but said he couldn't face going back to his child to admit he had failed.
Q 24Which playwright was hired to rewrite Marc Norman's screenplay for Shakespeare in Love?
Tom Stoppard
Tom Stoppard was recruited by the project's first director, a natural choice given that he had made his name with Rosencrantz and Guildenstern Are Dead, which retells Hamlet from the wings.
Q 25Which star was attached to play Viola in a 1991 version of Shakespeare in Love that collapsed?
Julia Roberts
Julia Roberts flew home and quit after the search for her leading man went nowhere, by which time the studio had already spent about $6 million on sets and costumes.
Q 26The star first cast as Viola in Shakespeare in Love insisted that only which actor could play Will?
Daniel Day-Lewis
Daniel Day-Lewis was sent roses with a card reading "Be my Romeo", her director recalls, but he was not interested, and when she could not talk him round she quit the film.
Q 27Which actress turned down Viola in Shakespeare in Love to make small independent films?
Kate Winslet
Kate Winslet, fresh from Titanic, left her lunch with the director apparently delighted, then phoned a week later to say no.
Q 28Shakespeare in Love's Best Picture win controversially defeated which film?
Saving Private Ryan
Saving Private Ryan would win a rematch: when the Hollywood Reporter polled hundreds of Academy members in 2015, they reversed the result by more than two to one.
Q 29In the year of Shakespeare in Love, which actress was Oscar-nominated for playing Elizabeth I in another film?
Cate Blanchett
Cate Blanchett was nominated for Elizabeth and lost, while the actress playing the same queen in Shakespeare in Love won a supporting Oscar that night for a far smaller part.
Q 30Which Oscars host opened the night Shakespeare in Love won dressed as Queen Elizabeth I?
Whoopi Goldberg
Whoopi Goldberg swept on in full royal regalia, a nod to a season with two films about the monarch, and announced to a roar of laughter, "I am the African Queen."