In 1989, Gilliam began working on the film after reading Cervantes' novel, but was unable to secure funding. In 1990, Phoenix Pictures and Gilliam agreed to make the film with Sean Connery. However, Gilliam ultimately decided that the budget the studio offered him was too low and dropped out to focus on The Defective Detective, another film he ultimately failed to make. In 1989, after the UK premiere of Fear and Loathing Las Vegas, Gilliam officially started working on the film with a budget of US$32.1 million from European financiers with Jean Rochefort as Quixote, and Johnny Depp as Grisoni. In September 2000, principal photography commenced in Navarre, Spain. However, in November, the production was ultimately shut down and cancelled due to sets and equipment destroyed by flooding, the departure of Rochefort due to illness, problems obtaining insurance for the production, and other financial difficulties. The original production became the subject of the 2002 documentary film Lost in La Mancha. Afterwards, 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.
Between 2003 and 2016, Gilliam made repeated attempts to relaunch production, with various actors attached as Grisoni and Quixote. However, all ended up being cancelled for various reasons, such as failing to secure funds, busy schedules and eventual loss of interest in the project, and John Hurt's cancer diagnosis and eventual death. Unexpectedly, in early June 2015, Gilliam secured a deal with Amazon Studios to release the film theatrically, followed by a streaming debut. In 2016, the film entered production once again with Adam Driver as Grisoni, and Jonathan Pryce as Quixote. By March 2017, Stellan Skarsgård, Olga Kurylenko, Joana Ribeiro, and Sergi López rounded out the film's cast. At the same time, principal photography commenced, and finally wrapped in early June. Filming took place throughout Spain. However, problems such as Amazon dropping out the film and legal disputes with producer Paulo Branco continued to plague the film. However, the film ultimately premiered on 19 May 2018 as the closing film of the 2018 Cannes Film Festival, where it received a fifteen-minute standing ovation.
The carnivalesque chaos is anchored in the cast's, especially Driver and Pryce's, charismatic performances.
Simon says The Man Who Killed Don Quixote receives:
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