- AFI's 100 Years... 100 Passions: #50
- 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.
- BFI Top 100 British Films: #49
- 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."
- 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.
- The Other Marty: Back when the film was first greenlit (see below) Simon Callow was cast as Henslowe. When the film finally entered production, Geoffrey Rush had become Henslowe and Simon was given the smaller role of Tilney.
- Playing Against Type:
- Real-Life Relative: Husband and wife team of Jim Carter (Ralph Bashford) and Imelda Staunton (Nurse).
- Role Ending Misdemanor: 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 conceived the idea of the movie in 1988. The movie was released ten years later.
- 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".
- What Could Have Been:
- The film was originally greenlit as a Julia Roberts vehicle back in the early 90s. Julia flew out to the UK to try and convince Daniel Day-Lewis to take the role of Shakespeare. He opted to do In the Name of the Father instead, and the project was shelved because no one could find a suitable alternative. Kenneth Branagh and Jude Law were also considered.
- Kate Winslet turned down the role of Viola to work on Jane Campion's Holy Smoke instead. Russell Crowe was offered the role of Shakespeare but refused to sign a four-picture deal with Miramax. 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. She 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.
- 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.
Trivia / Shakespeare in Love