Reference is made to Edward Alleyn on a promotional leaflet for one of 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.
The play being performed for the Queen at the beginning of the film is Two Gentlemen of Verona.
In one of the opening scenes, Shakespeare has a cup on his desk which reads, "Stratford Upon Avon", Shakespeare's birthplace.
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.
In the beginning of the movie, when Henslowe asks Will if he has been working on his play, and Will 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." Joseph Fiennes' brother, Ralph Fiennes, left his then-wife Alex Kingston (of "ER" (1994)) for Francesca Annis' who played his mother in a production of Hamlet.
The scene that show 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.
The priest near the beginning yells "a plague on both your houses", a famous quote from Romeo and Juliet.
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.
Counting this film's win for best picture, it has the most Oscars ever won (7) without winning the best director award.
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)
The lines "Was this the face that launched a thousand ships" that the actors recite during the audition come from Christopher Marlowe's play "Doctor Faustus".
Producer Edward Zwick was initially supposed to direct the film when Universal was involved; when Miramax finally went ahead with the project, Zwick was already working on The Siege (1998/I) and was unavailable. However, his production company - Bedford Falls - remained involved.
Writer Marc Norman got the idea for the film when his son Zachary called him from Boston University and suggested doing something on 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.
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.
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 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 Shakespeare. Some speculate that this friend is either Henry Wriothesley, earl of Southamption, or William Herbert, earl of Pembroke.
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 Shakespeare may actually have been illiterate.
In the first scene with Will 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.
In an interview Judi Dench said she had to wear such high heels for this film that director John Madden nicknamed her "Tudor Spice."
The boatman who rows 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."
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."
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."
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 eight 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 six minutes of the film.
Although long portions of Romeo and Juliet are used in this film, along with famous lines from many of Shakespeare's play, William Shakespeare is not credited in the film.
Simon Callow was originally cast as Philip Henslowe. However, after the project was re-activated, Geoffrey Rush was cast as Henslowe, and Callow was offered the smaller but key role of Tilney.
The street preacher at the start also points towards "The Rose Theatre" and proclaims "The Rose, smells thusly rank and would by any other name". This is an adaptation of a line which is found in Romeo and Juliet, the play at the centre of this film -- "That which we call a Rose would by any other name smell as sweet".