Terry Gilliam Film
- Cast the Runner-Up: Matt Damon and Heath Ledger were originally cast in opposite roles. They petitioned and switched their roles.
- Creator Backlash: Terry Gilliam was not happy with the finished film:"[I]t's not the film they wanted and it's not quite the film I wanted. It's the film that is a result of [...] two groups of people, who aren't working well together."
- Deleted Scene: An action scene early on in the film was cut because it was too spectacular and would be a Tough Act to Follow for the remaining action scenes. In the forest, a tree would come alive and attack the party. Angelika would be grabbed by its branches and thrown into the air.
- Enforced Method Acting: Matt Damon was strung up by his waist for the torture chamber scene. He could only stay up for 90 seconds at a time because the rope was crushing his ribs, cutting off his air supply. Terry Gilliam had a prosthetic made for him, but the studio didn't want the actor to wear it.
- Executive Meddling: Terry Gilliam fought with the Weinsteins during production. Bob Weinstein personally fired Cinematographer Nicola Pecorini after six weeks. As a result, the release was delayed by ten months.
- Fake Nationality: The German lead characters are played by an American (Matt Damon) and an Australian (Heath Ledger), both speaking with pronounced British accents, the (presumably) German Queen is played by an Italian (Monica Bellucci), the Italian Torture Technician is played by a Swede (Peter Stormare), and the French general is played by a Welshman (Jonathan Pryce).
- Money, Dear Boy: According to the DVD commentary, this is the reason Gilliam took the helm on this project in the first place.
- Playing Against Type: Terry Gilliam had talked Matt Damon out of wanting to play Will, intending the part for Heath Ledger. When Ledger read the script, he told Gilliam he wanted to play Jakob, surprising both Gilliam and Damon with the choice. Gilliam has stated he hopes audiences will be as excited to see the two playing against type as he was to direct them that way.
- Real-Life Relative: Terry Gilliam's son Harry is a stable-boy.
- Troubled Production: Gilliam had to deal with interference from the Weinsteins, actors dropping out and his cinematographer being replaced. One of the stars of the film, Lena Headey, noted that Gilliam was so upset about her casting in the film that he didn't even pretend that she wasn't his first choice (Gilliam's choice was Samantha Morton who the Weinsteins said was "too fat" much to the director's fury), and that Gilliam bullied her on the set. There were so many problems that Gilliam made Tideland, a film that was deliberately made to be as uncommercial as possible, during the making of this.
- What Could Have Been:
- Terry Gilliam and Matt Damon wanted Samantha Morton to play Angelika. But producers felt she was too chubby and the role went to Lena Headey instead.
- Gilliam wanted Johnny Depp for Will Grimm, but Bob Weinstein believed Depp was not commercially famous enough for the role. Damon joked that Weinstein "was kicking himself because half-way through production, Pirates of the Caribbean came out and Depp was all of a sudden a big sensation".
- Uma Thurman turned down the role of the Evil Queen, and Monica Bellucci was cast instead.
- Robin Williams was originally cast as Mercurio Cavaldi, but dropped out.
- Nicole Kidman turned down the role of Mirror Queen due to scheduling conflicts. Definitely good for her, since said conflicts were with widely acclaimed Dogville and Cold Mountain.
- Anthony Hopkins was originally cast as General Vavarin Delatombe, but dropped out due to scheduling conflicts.
