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.
Kenneth Branagh, Winona Ryder, Julia Roberts, and Daniel Day-Lewis were all considered for the lead roles.
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.
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."
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, left his then-wife Alex Kingston (of ER) 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: 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), and Universal Studios dropped the project when no suitable alternative was found. Joseph Fiennes was the only actor ever actually cast in the lead role.
Judi Dench won an Academy Award for her role as Queen Elizabeth, although she is onscreen for only about 6 minutes in four scenes.
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 his 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".
Kenneth Branagh, Winona Ryder, Jodie Foster and Meg Ryan were all considered for the lead roles at some point.
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