Judi Dench won an Academy Award for Best Performance by an Actress in a Supporting Role for her role as Queen Elizabeth, although she is on-screen for only about six minutes in four scenes. This is the second-shortest performance to win a Best Supporting Actress Oscar. The shortest ever performance was by Beatrice Straight in Network (1976), as she appeared in only five minutes of the film.
1998 was the only year that two actors were nominated for Academy Awards for playing the same character in two different films in the same year. Dame Judi Dench was nominated (and won) for Best Supporting Actress for playing Queen Elizabeth I in this movie and Cate Blanchett was nominated for Best Actress for portraying Elizabeth I in Elizabeth (1998). It is also worth noting that Joseph Fiennes portrayed the love interest in both of these films and that Geoffrey Rush was nominated for a BAFTA Award for his performance in each, winning for Elizabeth (1998).
Judi Dench was so taken with the full sized replica set of the Rose Theatre that Miramax gave it to her to take home when filming ended. Variety reported in early 1999 that she was looking for a site and a financial backer so it could be used as a working theater.
The unpleasant little urchin John Webster, who is shown playing with mice, grows up to be a big name of the next (Jacobean) generation of playwrights. His plays are known for their blood and gore, and his most famous title is "The Duchess of Malfi."
Will is shown signing a paper, with six illegible signatures visible. Several versions of Shakespeare's signature exist, all of which are different. This has led to debate about whether William Shakespeare may actually have been illiterate.
"Slate" Magazine reported that in 1999, when Queen Elizabeth II was preparing to bestow a new noble title to her son Prince Edward, she originally wanted to make him the Duke of Cambridge, but after he saw Shakespeare in Love (1998), he asked her if he could instead be the "Earl of Wessex," after Colin Firth's character "Lord Wessex," even though the character is villainous and unlikable. He requested and received the "Wessex" title and is sometimes known as Edward Wessex.
In the first scene with William Shakespeare, we see him crumpling up balls of paper and throwing them around the room which land near props which represent or refer to other works by Shakespeare. The first lands next to a skull - a reference to Hamlet and the second lands in a chest - a reference to the Merchant of Venice.
The boatman who rows William Shakespeare says, "I had that Christopher Marlowe in my boat once." This is a reference to the stereotypical remark of London taxi drivers about their famous customers: "I had that [famous name] in the back of my cab once."
About six years before the film was finally made, Julia Roberts was cast as Viola and flew to the UK to try to persuade Daniel Day-Lewis to take the part, but he declined in order to do In the Name of the Father (1993), so Universal Studios dropped the project when no suitable alternative was found. Joseph Fiennes was the only actor ever actually cast in the lead role.
The sonnet Will writes for Viola which begins with "Shall I compare thee to a summer's day?" is Sonnet 18. In reality, this sonnet, along with Sonnets number 1 to 126, were written for a male friend of William Shakespeare. Some speculate that this friend is either Henry Wriothesley, earl of Southamption, or William Herbert, earl of Pembroke.
In an interview Judi Dench said she had to wear such high heels for this film that director John Madden nicknamed her "Tudor Spice." (Ie, one of the Spice Girls, who were known by names such as Sporty Spice, Baby Spice, Scary Spice, etc.)
Reference is made to Edward Alleyn on a promotional leaflet for one of William Shakespeare's plays at the beginning of the film. Edward Alleyn, an actor in Shakespeare's time, ('Ned' in the film, played by Ben Affleck) was the real-life founder of the famous London private secondary schools Dulwich College and Alleyn's School.
Viola asks Will, "Are you the author of the plays of William Shakespeare?" This is a hint at the modern day speculation whether the works of Shakespeare were really written by him, or whether some nobleman (or another famous author) used his identity as a pseudonym. The film also manages to provide theoretical sources for the two prevailing academic theories about Shakespeare's inspirations for many of the sonnets: that they were written either for an extramarital mistress or a male lover.
Lord Wessex (played by Colin Firth) is the villain of the film and is generally presented as none too bright. Wessex's mistaken belief that it is Christopher Marlowe instead of William Shakespeare who has slept with Viola is particularly amusing given that it is the general historical and literary consensus that Marlowe was gay; something that (the film implies) Wessex would have known if he paid even a little bit of attention to the theater, arts, or culture of his age.
After initial test audiences had mixed reactions to the ending, a new version of Will and Viola's final scene was filmed in November 1998 (only weeks before release), which expanded upon the previously brief Twelfth Night projections in order to better handle their parting. In order to film the scene, Joseph Fiennes had to interrupt work on a West End play, and Gwyneth Paltrow had to be brought in from filming The Talented Mr. Ripley (1999).
The journeys up and down the Thames in river boats are taken from the puppet play Hero and Leander, which is written by the character Littlewit in Ben Jonson's Bartholomew Fair. Littlewit adapts the classical story of the lovers divided by the Hellespont to contemporary London.
The street preacher at the start points towards the Rose Theatre and proclaims "The Rose, smells thusly rank and would by any other name," is an adaptation of "That which we call a Rose would by any other name smell as sweet," which is a line in Romeo and Juliet; the play at the center of this film.
The last recipient of the short-lived Academy Award for Best Original Musical or Comedy Score, which the AMPAS only handed out for 4 years before discontinuing it. The other winners were Pocahontas (1995), Emma (1996) and The Full Monty (1997).
In the beginning of the movie, when Henslowe asks Will if he has been working on his play, and William Shakespeare answers "Doubt thou the stars are fire, Doubt that the sun doth move" he is quoting from Hamlet (Act II Scene 2). The lines are from a letter he wrote to Ophelia while pretending to have gone mad, and are followed by "Doubt truth to be a liar, but never doubt I love."
Henslow and Fennyman talk about paying the writer and actors. "Share of the profits," Fennyman suggests. "There's never any," responds Fennyman. This is in reference to the modern-day film practice of promising actors a share of a film's profits, then, through creative accounting, making it appear that a film did not turn a profit, thus bilking the actor of any more money.
William Shakespeare is shown playing Romeo in "Romeo & Juliet". Although no such claim appears in most biographies of Shakespeare, he is believed to have originated other famous roles in his own plays, such as The Ghost in "Hamlet," Old Adam in "As You Like It," and Lord Berowne in "Love's Labours Lost."
Writer Marc Norman got the idea for the film when his son Zachary called him from Boston University and suggested doing something on William Shakespeare as a young man in the Elizabethan theatre. It took two years for Norman to come up with the idea of having Shakespeare struggling with writer's block on "Romeo and Juliet."
Tom Stoppard added several characters in his work on the screenplay, including Christopher Marlowe. Some of his additions, including those regarding John Webster, were handled with caution, as it was feared some references would be too obscure.
Many plot elements from Romeo & Juliet (such as the opening duel, the tragic love story, and a balcony scene between two lovers) were later used in Edmond Rostand's Cyrano de Bergerac - a role played by Joseph Fiennes on stage.
Producer Edward Zwick was initially supposed to direct the film when Universal was involved. At that time Julia Roberts was cast as Viola, and the production got as far as having sets in the process of construction. However, Roberts had casting rights, and insisted on Daniel Day-Lewis. When he passed on the project, it fell through. When Miramax finally went ahead with the project, Harvey Weinstein decided to not hire Zwick to direct the film. However, Zwick's production company - Bedford Falls - remained involved.
After this film's five credited producers received Oscars for the Best Picture, the Academy of Motion Picture Arts and Sciences changed the rules the following year. Beginning with the 1999 awards, a maximum of three credited producers can be nominated to receive Best Picture statuettes, even if more than three are credited on-screen. This restriction was loosened slightly beginning with the 80th (2007) awards, when the following was added to the rules covering the award for Best Picture: "The [Producers Branch Executive] committee has the right, in what it determines to be a rare and extraordinary circumstance, to name any additional qualified producer as a nominee."
Actor and theatre owner Richard Burbage, who is a character in the film, in reality went on to play the title role in Shakespeare's revenge tragedy Hamlet. In the film, Burbage is shown coming to the theatre looking for revenge. There is a fight, which ends when Burbage gets hit with a skull; a reference to Yorick's skull which Hamlet famously meditates upon in the play.
The trivia item below may give away important plot points.
The scene that shows a woman (presumably Viola) nearly drowning in a shipwreck is a direct homage to one of the opening scenes of "Twelfth Night" (recently produced as Twelfth Night or What You Will (1996)), in which the character of Viola nearly drowns. However, considerable artistic license has been taken in this scene, as the play (a) does not open on a deserted beach (but in Orsino's court), and (b) not everyone drowns in the shipwreck (scene 2 has Viola discussing the near-drowning with the ship's captain, with other sailors present).