The Terry Gilliam Curse

A legendary catastrophic production "THE MAN WHO KILLED DON QUIXOTE" never got made (I hope it will). To document the production-hell, the documentary "Lost in La Mancha" was made.

Gilliam was excited to direct this film, as Quixote embodies many of the themes that run through his own work. Gilliam and his co-writer Tony Grisoni decided to create their very own version of the Quixote story.
Quixote was set to have been one of the biggest European films ever made, with a budget of $32.1 million, scaled back from an original $40 million. It was to have been one of Gilliam's most ambitious films, produced without any American financing.
Production originally commenced filming in October 2000, but stopped within a week due to a serious injury to Jean Rochefort, who had been cast for the title role of Don Quixote. Production was soon cancelled completely due to several on-set mishaps.

Shooting started in late October of 2000.
- The first location shoot was at a scenic, barren area north of Madrid, Spain, near a military base. Military fighter jets flew overhead repeatedly, ruining the audio recording and mandating a later re-dubbing in post-production.
- A flash flood on the second day of filming washed away equipment and changed the color of the barren cliffs, making the previous filming unusable.
- Rochefort, an able horseman, attempted to ride and act, but was obviously wincing in pain, and required assistance dismounting and walking. He flew to his doctor in Paris, where he was diagnosed with a double herniated disc. For several days the crew attempted to shoot scenes that did not involve Rochefort, but as time passed, it became apparent he would not be able to return. Gilliam decided this was a fatal wound to his project: He had spent two years casting the role of Don Quixote, and Rochefort had then spent seven months learning the English language for the part.
- The production was finally cancelled in November 2000, and the only result that was ever officially released was included in the 2002 documentary Lost in La Mancha, that chronicles the attempts to make this "film that didn't want to be made".
- After the production had been cancelled, an insurance claim was filed on behalf of the film's investors. US$15 million were reportedly paid, and the rights to the screenplay passed on to the insurance companies.

During the production of "Brazil", the project was sent into huge levels of debt. It was a lengthy quarreling between Gilliam and Universal Studios.
The studio battle for the final cut was epic, originating several documentaries and a book.
Gilliam lost that battle, and the first theatrical release, as well as the TV edit, had a "sweet" happy ending that Gilliam never intended.
However, he got his way in the end wih the release from the Criterion Collection, which had three different cuts of the film, including the Gilliam-approved version. (Unfortunately, the Criterion Collection is highly expensive)
So, all in all in the end, not many people have seen the actual film.

The Adventures of Baron Munchausen also had budget problems.
In another not-so-good production, the budget was surpassed and ended up doubling the figures (planned at 23 million and costing almost 47)!

After arriving in Rome for the shoot in September 1987, Gilliam's crew during all of the principal photography had to face the fact that producer Schühly hadn't properly organized material, money, and personnel, and thus the whole production seemed constantly undersupplied. From October 1987, shooting was moved to Spain. Meanwhile, the film's insurance company Film Finances became increasingly concerned about the budget, and took hold of the film's finances, setting a deadline for all photography of November 7. Film Finances threatened to sue Gilliam for fraud as the film wasn't finished, and to replace him. (However, they were in no position to do so).
On top of it all, it was then that unpaid bills amounting to 5 million dollars were found in Schühly's office. Negotiations took place, after which shooting was resumed at Cinecittà on November 23, under the premise that several scenes had to be cut altogether or at least dramatically reduced. The production finally came to a successful closure.

It earned only about $8 million in US ticket sales, as it saw no wide domestic release (it was shown in about 120 theatres) due to financial issues at Columbia Pictures, which was in the process of being sold at the time, and couldn't successfully manage the USA release.
Grossing only $8 million, it became one of the biggest flops of all time.

Fear and Loathing in Las Vegas by Hunter S. Thompson was renowned for the numerous failed attempts to adapt it to the big screen. Some directors were invited; one of them stated he couldn't see "how you could get that one on the screen." It took years to take off, with even some casting choices growing too old for the parts.

Gilliam finally pulled it together, eventually gathering a nice budget and a good cast.
A fight erupted between Gilliam and the WGA over writing credits. The WGA wouldn't allow Cox and Davies (two writers who had produced a previous script) to be removed from the film credits, even though none of their material was used in the film. The conflict ended with Gilliam publicly burning his WGA card.
Gilliam felt that it was not a well-organized film and said, "Certain people didn't... I'm not going to name names but it was a strange film, like one leg was shorter than the other. There was all sorts of chaos".
Despite being a cult favorite, the film was widely panned.
Having cost $18.5 million, it grossed only $10.6.

The film got the greenlight in April of 2003, and started filming in June.
During production, Gilliam often disputed with executive producers Weinstein. Shooting was soon finished in December.
Things had been going a bit too smoothly for a frighteningly long time. But there it came - a violent "battle of egos" with Weinstein, who had had Gilliam's cinematographer replaced halfway through shooting, and was irritating the director by interfering with editing.
As a result, editing was put on hiatus. Post-production was severely delayed when Gilliam disagreed with the Weinsteins over the final cut privilege. In the meantime, the conflict lasted so long that Gilliam had enough time to shoot all of Tideland.

Finally, the film was released on August 26, 2005. It cost $80 million, and, although it brought just under $38 million in the USA, it grossed a worldwide total of $105.32 million.

Gilliam was filming this when, sadly, Heath Ledger died.

In the mid-1990s, Gilliam and Charles McKeown developed a script for TIME BANDITS 2; the project never came to be, as several of the original actors had died.

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He also attempted to direct a version of Charles Dickens's A Tale of Two Cities, which collapsed due to disagreements over its budget and choice of lead actor.

He's had other shelved projects and films that he has long been trying to get off the ground.

Not all is catastrophic, as 12 Monkeys did pretty good, as did The Fisher King; and Tideland, although not a commercial success, had, I believe, a smooth-running production.