Judi Dench won an Academy Award for Best 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 Actress in a Supporting Role Oscar. The shortest ever performance was by Beatrice Straight in Network (1976), as she appeared in only five minutes of the film.
Gwyneth Paltrow saw the script at Winona Ryder's office table in 1997 and asked her if she could read it. Paltrow got the part without telling Ryder she was going to try for it. The former friends haven't been friends since because of Paltrow's selfishness, later winning an Oscar for the part.
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).
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 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."
Wabash (Henslowe's tailor, who has gotten a role not because of any acting experience but just because Henslowe owes him money) has a stutter, but his stutter disappears almost entirely when he is acting onstage. This is an actual phenomenon that is well-known to speech therapists and other modern-day pathologists who study and treat stuttering. Many actors who are former stutterers first entered the profession when it was recommended to them as therapy for their speech impediment; famous actors who turned to acting to help their stuttering include James Earl Jones, Emily Blunt, Bruce Willis, Nicholas Brendon, and Sam Neill.
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.
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.
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.
"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. Before Edward received the title, the most recent man known as Earl of Wessex was Harold Godwinson, before he became King Harold II in 1066.
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.
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).
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.
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."
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.
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.
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."
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).
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.
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.
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.
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.
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.
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."
In the final scene, Will tells Viola "You will never age for me, nor fade, nor die." He is paraphrasing Sonnet 18: "Thy eternal summer shall not fade, nor lose possession of that fair thou owest. Nor shall death brag thou wand'rest in his shade, when in eternal lines to time thou growest."
The film was considerably reworked after the first test screenings. The scene with Shakespeare and Viola in the punt was re-shot, to make it more emotional, and some lines were re-recorded to clarify the reasons why Viola had to marry Wessex. The ending was re-shot several times, until Tom Stoppard eventually came up with the idea of Viola suggesting to Shakespeare that their parting could inspire his next play.
During an interview with Howard Stern in January 2015, Gwyneth Paltrow opened up about how she initially turned down the part of Viola de Lesseps, citing emotional distress following her breakup with Brad Pitt. Paltrow told Stern that she was "very sad" and said, "'I'm not going to work' and all that nonsense". Eventually, she was persuaded by Miramax producer 'Paul Webster' to go out for the role, and the rest is Oscar history.
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.
Judi Dench plays Queen Elizabeth I in this film. Both Geoffrey Rush and Joseph Fiennes had starring roles in the movie Elizabeth (1998) the same year which centers on Queen Elizabeth's life. Rush and Finennes played important figures of Queen Elizabeth's life, Rush played Sir Francis Walsingham and Fiennes played Robert Dudley, Earl of Leicester.
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).