- All-Star Cast: The film features a line-up of very accomplished British theatre actors - Joseph Fiennes, Judi Dench, Imelda Staunton, Simon Callow, Martin Clunes, Rupert Everett among others. There are also film stars such as Ben Affleck, Colin Firth and Tom Wilkinson. Retroactively for Gwyneth Paltrow, see below.
- Cast the Runner-Up:
- Harvey Weinstein asked Ben Affleck to play William Shakespeare, but he declined, and played Edward Alleyn instead.
- Colin Firth was also considered for Shakespeare. He was eventually cast as Lord Wessex.
- 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.
- Fake Brit: Australian actor Geoffrey Rush dons a cockney accent to play Philip Henslowe. Gwyneth Paltrow likewise does a near-flawless English accent as Viola. Ben Affleck too, or as he puts it "I was the only person in the cast who hadn't been knighted."
- Inspiration for the Work: 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.
- Life Imitates Art: Colin Firth's character has the title "Earl of Wessex", non-existent at the times the film was either set or written (or any time since the Norman Invasion, in fact). When Prince Edward was offered a title on getting married in 1999, he asked to have this title reinstated for him, reportedly because he saw this film and liked the sound of it.
- Playing Against Type:
- Colin Firth in a period romantic comedy...as the Prince Charmless whom you don't want the heroine to end up with.
- There's also Ben Affleck in an Elizabethan period piece, playing a pompous flamboyant actor.
- Real-Life Relative: Husband and wife team of Jim Carter (Ralph Bashford) and Imelda Staunton (Nurse).
- Role-Ending Misdemeanor: Robert Lindsay lost out on a part because he had previously confronted producer Harvey Weinstein over his behaviour on Strike It Rich.
- Romance on the Set: Gwyneth Paltrow and Ben Affleck were dating at the time, Ben taking the role in order to be near her.
- Saved from Development Hell: Marc Norman got the idea in 1988 and it was suggested by his son. He then wrote a draft screenplay which he presented to Edward Zwick, which attracted Julia Roberts, who agreed to play Viola. However, Zwick disliked Norman's screenplay and hired Tom Stoppard to improve it. The film then went into production in 1991 at Universal with Zwick as director, but although sets and costumes were in construction, the role Shakespeare had not yet been cast because Roberts insisted that only Daniel Day-Lewis could play the role. Day-Lewis was uninterested, and when Roberts failed to persuade him, she withdrew from the film, six weeks before shooting was due to begin. The production then went into turnaround and Zwick was unable to persuade other studios to take up the screenplay. Zwick eventually managed to persuade Miramax to make the film, but they installed John Madden as director. It was finally completed in 1998, a decade after it was first conceived.
- Star-Making Role:
- Gwyneth Paltrow had been making headway with notable performances in 7 and Emma but her Oscar winning performance in this really solidified her as a star.
- Defied to an extent by Joseph Fiennes. After the double successes of this and Elizabeth he was offered many different roles but turned them down to focus on theatre work.
- Uncredited Role:
- No conclusive evidence exists as to why Rupert Everett was uncredited for his role as Christopher Marlowe. However, regarding his performance, Everett was quoted by US Weekly as saying "I was very, very bad in it - I was a bundle of f—-ing hideous nerves".
- John Inman as an actor playing Lady Capulet.
- What Could Have Been:
- Russell Crowe was offered the role of Shakespeare but refused to sign a four-picture deal with Miramax. Kenneth Branagh, Ralph Fiennes, Mel Gibson, Hugh Grant, Paul McGann and Jude Law were also considered.
- Kate Winslet turned down the role of Viola to work on Jane Campion's Holy Smoke instead. Other candidates included Rosanna Arquette, Kim Basinger, Jodie Foster, Daryl Hannah, Helen Hunt, Ashley Judd, Nicole Kidman, Diane Lane, Michelle Pfeiffer, Meg Ryan, Sigourney Weaver, and Robin Wright.
- Gwyneth Paltrow also initially turned the role of Viola down, as she was going through a bad break-up and didn't want to work. Miramax producer Paul Webster eventually convinced her to take the role. Winona Ryder claims Paltrow saw the script in her home and asked her if she could read it, and got the part without telling Ryder she was going to try for it. Paltrow strongly denies Ryder's claim.
- After initial test screenings, the film was heavily re-edited. The scene in the punt was re-shot to make it more emotional, and some lines had to be re-recorded to make it clearer why Viola had to marry Wessex. The ending also had to be re-shot several times before they were happy.
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