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50 free Shakespeare in Love trivia questions with answers — entertainment quiz, new questions added Aug 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 50 questions with answers and explanations. Play the quiz
Q 01Who directed Shakespeare in Love?
John Madden
He had just directed Mrs Brown; Zwick, the original director, ended up as a producer.
Q 02Who plays William Shakespeare?
Joseph Fiennes
The same year he played Robert Dudley in Elizabeth, another Best Picture nominee.
Q 03What is the name of Gwyneth Paltrow's character?
Viola de Lesseps
The role earned Paltrow the Academy Award for Best Actress.
Q 04Which play is Shakespeare writing during the film?
Romeo and Juliet
It begins life as a comedy with a much sillier title.
Q 05What is the working title of Will's stalled comedy at the start of the film?
Romeo and Ethel, the Pirate's Daughter
Marlowe hands him the plot that turns it into a tragedy.
Q 06Under what male name does Viola audition?
Thomas Kent
The Queen later pretends Kent is simply a man with a remarkable resemblance to a woman.
Q 07Which theatre does Philip Henslowe own in the film?
The Rose
Burbage's rival Curtain Theatre hosts the play after the Rose is shut down.
Q 08Who plays Henslowe?
Geoffrey Rush
He earned a Best Supporting Actor nomination for it, one of three costume dramas he made in 1998.
Q 09Who plays Queen Elizabeth I?
Judi Dench
The role won her the Best Supporting Actress Oscar.
Q 10Roughly how much screen time did Dench joke she had when accepting her Oscar?
Eight minutes
She quipped that she should only get a little bit of the statuette.
Q 11Which aristocrat is Viola betrothed to?
Lord Wessex
The Earl of Wessex title had not existed for over 500 years in Shakespeare's day.
Q 12Who plays Wessex?
Colin Firth
Prince Edward reportedly asked for the Wessex earldom after seeing Firth's character.
Q 13How much is the wager over whether a play can show the true nature of love?
£50
It is exactly the sum Will needs to buy a share in the Chamberlain's Men.
Q 14Which fellow playwright does Will impersonate when confronted by Wessex?
Q 21The Queen tells Will to write something more cheerful next time, for which occasion?
Twelfth Night
The final image imagines a woman named Viola disguised as a man after a shipwreck.
Q 22Viola's disguised audition speech comes from which play?
The Two Gentlemen of Verona
Kent then runs off when Will starts asking questions.
Q 23Who first suggested the idea for the film to screenwriter Marc Norman?
His son
Norman's son Zachary floated it in the late 1980s.
Q 24Which playwright was hired to rewrite Norman's screenplay?
Christopher Marlowe
When Marlowe is later killed, a guilt-ridden Will assumes Wessex ordered the murder.
Q 15Who plays Marlowe?
Rupert Everett
He shares a scene with Martin Clunes's Burbage over payment for The Massacre at Paris.
Q 16Which role does Ben Affleck play?
Ned Alleyn
The Miramax boss persuaded him to take the small part of the leading tragedian.
Q 17The creepy boy who plays with mice and enjoys Titus Andronicus grows up to be which real playwright?
John Webster
His plays The Duchess of Malfi and The White Devil are famous for their gore.
Q 18Why is the Rose closed down by the Master of the Revels?
A woman has been acting on stage
Webster spies on the lovers and informs Tilney.
Q 19Why does Viola end up playing Juliet on opening day?
The boy actor's voice breaks
Will himself has taken the role of Romeo after losing his lead actor.
Q 20Where does the Queen order Viola to sail with Wessex?
Virginia
It's an anachronism: the Colony of Virginia did not yet exist.
Tom Stoppard
His first big success had been the Shakespeare-themed Rosencrantz and Guildenstern Are Dead.
Q 25Which star was attached to play Viola in the 1991 Universal version that collapsed?
Julia Roberts
She walked out six weeks before shooting, and canceling cost Universal $6 million.
Q 26Roberts insisted that only which actor could play Shakespeare?
Daniel Day-Lewis
He wasn't interested, and she withdrew when she couldn't persuade him.
Q 27Which actress turned down Viola after the success of Titanic?
Kate Winslet
She chose to pursue independent films instead; Ryder, Diane Lane and Robin Wright were also considered.
Q 28The film's Best Picture win controversially defeated which movie?
Saving Private Ryan
It was the first comedy to win Best Picture since Annie Hall.
Q 29Which actress was the Best Actress frontrunner that Paltrow beat?
Cate Blanchett
Blanchett was nominated for playing the same queen, Elizabeth I, in Elizabeth.
Q 30How many Oscars did Shakespeare in Love win?
Seven
It led the field with thirteen nominations.