Terry Gilliam’s Long, Strange, (Not Yet) Doomed ‘Don Quixote’ Quest

Since 1998, the ‘Brazil’ helmer’s passion project has been plagued by floods, illness, money problems, and Johnny Depp’s busy schedule. Now, a new version is finally filming.

Everett Collection

When news broke earlier this week that production had commenced on Terry Gilliam’s The Man Who Killed Don Quixote, it was difficult not to take the announcement with grains upon grains of salt. That’s not because of the material itself: a modernized reimagining of Miguel de Cervantes’ 1605 fable about foolish old Don Quixote, who believes himself a knight and goes off in search of adventure with his portly companion Sancho Panza by his side. Nor was it because of its pedigree, with Gilliam at the helm and Adam Driver and Jonathan Pryce leading the cast, it has credibility to spare. Rather, it’s because Gilliam, and cinephiles, have been down this path numerous times before.

And, so far, it’s only led to heartbreaking disaster.

The odyssey of The Man Who Killed Don Quixote is one of an artist mirroring his art, of cinematic devotion in the face of unrelenting opposition and misfortune, and of a “jinxed” project that its obsessive maker simply won’t abandon. It begins as far back as the early ‘90s, when Gilliam—the former Monty Python member who moved on to direct surreal, idiosyncratic works like Brazil, Time Bandits, Twelve Monkeys and Fear and Loathing in Las Vegas—first got the idea to turn Cervantes’ Don Quixote into a feature. The twist, however, was that his story, dubbed The Man Who Killed Don Quixote, would concern a modern-day advertising executive named Toby Grisoni who finds himself magically transported back to 17th century Spain, where he soon finds himself tilting at windmills beside Quixote.

In 2000, Gilliam’s film was on its way, albeit with only foreign funding—and with a $32.1 budget, it was one of the most expensive European-financed productions ever mounted. As a director whose fanciful ambitions often exceeded his budgetary grasp (a situation that previously led to disaster on 1988’s The Adventures of Baron Munchausen), Gilliam was again embarking on an endeavor that, from the outset, was poised precariously between triumph and failure. What followed has since become the stuff of cine-legend, thanks to the fact that Gilliam had filmmakers Keith Fulton and Louis Pepe documenting the making of The Man Who Killed Don Quixote in Madrid. When the film fell apart, it did so in front of their cameras.

The result was Lost in La Mancha, a behind-the-scenes documentary about the movie’s ultimate collapse. Courtesy of a margin-less schedule and numerous, ruinous “acts of God” including location-destroying flash floods, roaring F16 fighter jets that made dialogue recording impossible, and the poor health of French star Jean Rochefort—who, after spending seven months learning English to play Quixote, became so crippled by double herniated discs that he had to abandon the role—Fulton and Pepe’s non-fiction film is like watching an inevitable train wreck in slow motion. Even though Gilliam was determined to press forward with filming, and had footage in the can of both Rochefort on horseback (if just barely) and co-star Johnny Depp in shackles (and tussling with a fish), The Man Who Killed Don Quixote died unceremoniously in the Spanish plains.

“Without a battle, maybe I don’t know exactly how to approach it,” says Gilliam in Lost in La Mancha, and though it’s clear that his Quixote’s failure was largely due to forces out of his control, there’s a sense throughout that documentary—and any overview of his career—that the director thrives off disarray (no wonder his first assistant director dubbed him “Captain Chaos”). The project’s collapse was traumatic for Gilliam, but he soldiered on, only to find that there were more headaches ahead, be it clashes with Miramax’s Harvey Weinstein over 2005’s The Brothers Grimm (with Matt Damon and Heath Ledger), or the untimely death of Ledger during filming of 2009’s The Imaginarium of Doctor Parnassus, which (in an interview with IFC at the time) had Gilliam thinking that it was Quixote all over again: “That was the first clear thought: it’s over!”

Nonetheless, it soon became clear that nothing would kill Gilliam’s desire to make The Man Who Killed Don Quixote. While he made some public intimations as early as 2005 that he was thinking of restarting the movie with Gerard Depardieu as his new Quixote, it wasn’t until 2008 that things truly began to sound promising, this time with Gilliam’s fellow Pythonite Michael Palin (coaxed out of retirement) as Quixote, and Depp remaining as Grisoni. That also wasn’t to be, however, and in a 2009 interview with Collider, Robert Duvall revealed that he was now in talks to play Quixote, opposite Ewan McGregor as Grisoni. By 2010, financing on that iteration had collapsed, with Gilliam telling Variety, “Don Quixote gives me something to look forward to, always. Maybe the most frightening thing is to actually make the film.”

Determined, like Quixote, to make his dream a reality at any cost, Gilliam pressed onward. In 2014, he told Maxim, “I think it’s just simple pigheadedness, because it’s so stupid to do what I’m doing; so romantic, and not at all pragmatic. Recently, I’ve decided to call it a tumor that’s growing inside me. Until I excise the tumor, I won’t ever be able to live my life properly again.” At the 2015 Cannes Film Festival, the director struck a distribution deal with Amazon to, among other things, produce and distribute Quixote, this time with John Hurt as Quixote and Jack O’Connell as Grisoni. With Amazon’s money behind it, the film actually sounded like it might make it to the finish line—but Hurt’s pancreatic-cancer diagnosis shortly thereafter (which later claimed his life) again brought things to a halt.

Still, by mid-2016, the movie was back on track, with Palin recommitting to the role of Quixote and Adam Driver as Grisoni—now reconceived as an advertising director. At Cannes that year, Gilliam sounded optimistic, claiming that Driver was, “the guy I’ve been looking for all these years,” and stating that, “We should be here in Cannes next year with the finished film, and then you can ask me why I made such a mess of it or why I made such a wonderful film.” That projection, unsurprisingly, soon came to seem premature, as funding issues—reportedly due to producer Paulo Branco not delivering the money he’d promised—halted production days before the cameras were to roll last September.

Now, however, The Man Who Killed Don Quixote is apparently shooting, with Palin out and Pryce in as Quixote—meaning Gilliam’s decades-long Sisyphean mission may finally be nearing completion. “We are still marching forward. It is not dead. I will be dead before the film is,” the director told BBC Radio 2’s Jonathan Ross last September. And while one hopes that isn’t the case, it’s a sentiment that perfectly sums up a filmmaker who, like Quixote, can’t stand the thought of living in a world that doesn’t have room for his outsized imagination.

If Quixote makes it to the screen, it’ll be not only an against-all-odds miracle, but also a testament to its maker’s indefatigable belief in, and need for, cinematic magic. The windmill-tilting, apparently, never ends.