In 1593 London, William Shakespeare is a sometime player in the Lord Chamberlain's Men and poor playwright for Philip Henslowe, owner of The Rose Theatre. Shakespeare is working on a new comedy, Romeo and Ethel, the Pirate's Daughter. Suffering from writer's block, he has barely begun the play, but starts auditioning players. Viola de Lesseps, the daughter of a wealthy merchant, who has seen Shakespeare's plays at court, disguises herself as "Thomas Kent" to audition, then runs away. Shakespeare pursues Kent to Viola's house and leaves a note with the nurse, asking Thomas Kent to begin rehearsals at the Rose. He sneaks into the house with the minstrels playing that night at the ball, where her parents are arranging her betrothal to Lord Wessex, an impoverished aristocrat. While dancing with Viola, Shakespeare is struck speechless, and after being forcibly ejected by Wessex, uses Thomas Kent as a go-between to woo her. Wessex also asks Will's name, to which he replies that he is Christopher Marlowe.
When he discovers her true identity, they begin a secret affair. Inspired by her, Shakespeare writes quickly, with help from his friend and rival playwright Christopher 'Kit' Marlowe, completely transforming the play into what will become Romeo and Juliet. Then, Viola is summoned to court to receive approval for her proposed marriage to Lord Wessex. Shakespeare accompanies her, disguised as her female cousin. There, he persuades Wessex to wager  50 that a play can capture the true nature of love, the exact amount Shakespeare requires to buy a share in the Chamberlain's Men. Queen Elizabeth I declares that she will judge the matter, when the occasion arises.
When Richard Burbage, owner of the Curtain, finds out that Shakespeare has cheated him out of both money and the play, he goes to the Rose Theatre with his Curtain Theatre Company and starts a brawl. The Rose Theatre company drives Burbage and his company out and then celebrate at the local pub.
Viola is appalled when she learns Shakespeare is married, albeit separated from his wife, and she realises she cannot escape her duty to marry Wessex. Will discovers that Marlowe is dead, and thinks he is to blame. Lord Wessex suspects an affair between Shakespeare and his bride-to-be. Because Wessex thinks that Will is Kit Marlowe, he approves of Kit's death, and tells Viola the news. It is later learned that Marlowe had been killed in an accident. Viola finds out that Will is still alive, and declares her love for him.
When Edmund Tilney, the Master of the Revels, is informed there is a woman player at The Rose, he closes the theatre for breaking the ban on women. Viola's identity is exposed, leaving them without a stage or lead actor, until Richard Burbage offers them his theatre. Shakespeare takes the role of Romeo, with a boy actor as Juliet. Following her wedding, Viola learns that the play will be performed that day, and runs away to the Curtain. Planning to watch with the crowd, Viola overhears that the boy playing Juliet cannot perform, and offers to replace him. While she plays Juliet to Shakespeare's Romeo, the audience is enthralled, despite the tragic ending, until Master Tilney arrives to arrest everyone for indecency due to Viola's presence.
But the Queen is in attendance and restrains Tilney, instead asserting that Kent's resemblance to a woman is, indeed, remarkable. However, even a queen is powerless to end a lawful marriage, and she orders Kent to "fetch" Viola because she must sail with Wessex to the Colony of Virginia. The Queen also tells Wessex, who followed Viola to the theatre, that Romeo and Juliet has won the bet for Shakespeare, and has Kent deliver his  50 with instructions to write something "a little more cheerful next time, for Twelfth Night".
Viola and Shakespeare say their goodbyes, and he vows to immortalise her, as he imagines the beginnings of Twelfth Night, imagining her as a castaway disguised as a man after a voyage to a strange land.After the film's release, certain publications, including Private Eye, noted strong similarities between the film and the 1941 novel No Bed for Bacon, by Caryl Brahms and S. J. Simon, which also features Shakespeare falling in love and finding inspiration for his later plays. In a foreword to a subsequent edition of No Bed for Bacon (which traded on the association by declaring itself "A Story of Shakespeare and Lady Viola in Love") Ned Sherrin, Private Eye insider and former writing partner of Brahms', confirmed that he had lent a copy of the novel to Stoppard after he joined the writing team, but that the basic plot of the film had been independently developed by Marc Norman, who was unaware of the earlier work.
The film's plot can claim a tradition in fiction reaching back to Alexandre Duval's "Shakespeare amoureux ou la Piece a l'Etude" (1804), in which Shakespeare falls in love with an actress who is playing Richard III.
The writers of Shakespeare in Love were sued in 1999 by bestselling author Faye Kellerman. She claimed that the plotline was stolen from her 1989 novel The Quality of Mercy, in which Shakespeare romances a Jewish woman who dresses as a man, and attempts to solve a murder. Miramax Films spokesman Andrew Stengel derided the claim, filed in the US District Court six days before the 1999 Academy Awards, as "absurd", and argued that the timing "suggests a publicity stunt".
Output: Who must Viola sail the the Colony of Virginia with?