- Dawson Casting: Lily Cole was in her twenties during filming, but her character is 15 for most of it. She even spends some time masquerading as a 12 year old, which she says is obviously not true. It's inverted when Cole plays Valentina's mother as well as Valentina when she's older and has a child.
- Doing It for the Art: At Johnny Depp's suggestion, he, Colin Farrell and Jude Law all donated their salaries to Heath Ledger's daughter.
- Fake Brit: The overall cast is quite a diverse example, as it features an American (Johnny Depp), a Canadian (Christopher Plummer), an Australian (Heath Ledger) and an Irishman (Colin Farrell) all playing English characters. None of these characters seem to actually come from England, however.
- In Memoriam: During the credits: "In memory of Heath Ledger and William Vince", followed by a mirror reflection of Ledger as his character Tony. Vince was a co-producer on the film, who passed away from cancer in June 2008.
- Serendipity Writes the Plot: Heath Ledger's tragic death led Terry Gilliam to invent the concept where Tony takes on a different face every time he enters the mirror. Johnny Depp, Colin Farrell, and Jude Law all donated their salaries to Ledger's daughter so she could have a trust in her name when she becomes an adult. Gilliam later remarked that the concept worked so well that his editing team were surprised this wasn't the original idea to begin with.
- Throw It In!:
- According to director Terry Gilliam, Heath Ledger frequently went off-script, which inspired Andrew Garfield to do the same.
- Apparently Verne Troyer came up with all the talk about midgets by himself. Considering his stature, it was considered okay for him to say it.
- Troubled Production: Against all odds, the film was completed despite the sudden death of its lead actor - and with a refreshing lack of Fake Shemp, thanks to a bit of Real Life Writes the Plot, to the extent that Heath Ledger was actually given a screenwriting credit.
- After Ledger's death, producer William Vince died only two days after filming wrapped, and Gilliam broke his vertabrae after being hit by a car during post-production, narrowly avoiding a shutdown.
- What Could Have Been:
- Gemma Arterton, Abbie Cornish, Romola Garai, Jena Malone and Mia Wasikowska were considered for Valentina.
- Dominic Cooper auditioned for Anton.
- Tom Cruise expressed interest in being one of the alternate versions of Tony, but Gilliam wanted to "keep this in the family" and only use actors who had been close to Ledger.
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