f you were to just look at the beginning of their careers, Terry Gilliam and Johnny Depp seemingly had completely opposite trajectories. Gilliam started out crafting wacky animations for the British comedy troupe Monty Python in the late ’60s, while Depp got his big break as an ’80s heartthrob thanks to 21 Jump Street. However, a study of their later work clearly shows how the two creative minds were ultimately destined to intersect.

Gilliam went on to become a director of feature films, and made a name for himself in Hollywood by creating surreal, visually captivating sci-fi and fantasy films like Time Bandits, Brazil, The Adventures of Baron Munchausen, and 12 Monkeys.

When Johnny Depp completely transformed for Tim Burton’s Edward Scissorhands in 1990, it showed his willingness to challenge himself creatively and foreshadowed the oddball roles that he would take on later in his career.

Johnny Depp and Terry Gilliam: Exploring Their Creative Partnership

While they haven’t worked with each other often, Gilliam’s imaginative mind and Depp’s ability to be right at home in strange cinematic worlds have helped the two resonate as an impactful collaborative duo. Here’s a brief look at the creative partnership between Terry Gilliam and Johnny Depp.

Fear and Loathing in Las Vegas and The Imaginarium of Doctor Parnassus

Terry Gilliam and Johnny Depp first teamed up in 1998 for Gilliam’s adaptation of the Hunter S. Thompson 1971 novel Fear and Loathing in Las Vegas.

Written in gonzo journalism style, the story follows the drug-induced hijinks of Raoul Duke (a fictionalized version of Thompson himself) and Dr. Gonzo (based on Oscar Zeta Acosta, an attorney and activist who became friends with Thompson) as they make their way through Sin City.

Depp wasn’t the first choice to play Duke, but after he met with Thompson, the author became convinced that Depp was the only actor who could best encapsulate the role. Benicio del Toro was ultimately cast as Dr. Gonzo, and the rest is history.

Related video: Johnny Depp Made $650 Million During His Heyday In Hollywood, But His Biggest Payout Was Not A ‘Pirates Of The Caribbean’ Movie (Dailymotion)

While Fear and Loathing in Las Vegas was a box office disaster that received mixed critical reviews, Depp’s performance earned him a Best Foreign Actor award from the Russian Guild of Film Critics, and Gilliam received a Palme d’Or nomination at the Cannes Film Festival for his skilled directing.

The movie went on to become a cult classic, and launched a lasting friendship between Gilliam and Depp.

The next feature-film collaboration between the actor and director to see the light of day (we’ll get into the failed collaboration that happened in between in a little bit) came in 2009 with The Imaginarium of Doctor Parnassus.

The fantasy film, which tells the story of a theater troupe leader who makes a bet with The Devil, takes him on a journey through a bizarre dream world, starred Heath Ledger in the lead role of Tony Shepard.

Sadly, Ledger died from a drug overdose halfway through filming, leading Gilliam to cast Depp, Colin Farrell, and Jude Law as different transformations of Shepard.

As it turns out, Depp was Gilliam’s first call, not only because of Depp and Ledger’s friendship and the physical similarities between the two, but also because Ledger had actually channeled Depp for his initial performance, which Gilliam touched on during a 2009 interview with CBS News.

“That’s what’s funny, when Johnny appears so many people think it’s Heath! And it’s a trick: Johnny’s not doing anything. He looks like Johnny. […] [During the initial shoot] Heath was on stage and the Russians are appearing, and he was behaving in a very funny way, he was moving around, and I said, ‘Heath, I know what you’re doing.’ He said,

‘What are you talking about?’ ‘You’re doing Johnny Depp, aren’t you?’ And can you believe, that helps this transition [when Ledger enters the mirror and becomes Depp]. This was not intended!”

The Imaginarium of Doctor Parnassus was better received both commercially and critically than Gilliam and Depp’s first outing, as it grossed $64.4 million on a $30 million budget and earned two Academy Award nominations (Best Costume Design and Best Art Direction).

The Failed Don Quixote Movie

Terry Gilliam’s Don Quixote movie took nearly 30 years to make, and it was such a developmental disaster that it spawned not one, but two making-of documentaries: Lost in La Mancha and He Dreams of Giants.

Gilliam first started work on his adaptation of the Miguel de Cervantes epic in 1989, though the film didn’t start pre-production until 1998.

Fresh off his performance in Fear and Loathing in Las Vegas, Depp was cast as Toby Grummett, a marketing executive who travels back in time to 17th-century Spain, where he meets Don Quixote, initially played by French actor Jean Rochefort.

On-set issues and Rochefort’s mounting health problems led to production being canceled.

Gilliam’s attempts to revive the project began in 2003, and while Depp stayed loosely attached through the mid-2000s, his busy schedule kept him from fully committing to the project, and he was officially replaced by Ewan McGregor in 2010.

Several re-castings, controversies, and a new producer later, The Man Who Killed Don Quixote finally came out in 2018, with Adam Driver as film director Toby and Jonathan Pryce as Javier Sanchez, a Spanish cobbler who thinks he’s Don Quixote.

Despite Depp and Gilliam’s failure to successfully launch their planned Don Quixote vehicle, a third creative endeavor between the two may soon be in the works.

Another Project in the Works?

In early December, Gilliam teased another potential collaboration with Depp on his new apocalyptic comedy film. Attending the Red Sea Film Festival in Saudi Arabia for a double screening of Lost in La Mancha and He Dreams of Giants, Gilliam briefly summarized the plot for Carnival at the End of Days during an interview with Variety, during which he made clear that he’s gunning for Depp to be the main attraction.

“God wipes out humanity and the only character who wants to save them is Satan, and Johnny Depp plays Satan.”

Production on the film is still in its early stages, though Gilliam seems pretty confident that Depp will sign on.

Judging from Gilliam’s description of the film, it seems like a project right up the three-time Academy Award nominee’s alley.

“This is a simple tale of God wiping out humanity for f****** up his beautiful garden Earth,” Gilliam said. “There’s only one character who’s trying to save humanity and that’s Satan, because without humanity he’s lost his job and he’s an eternal character and so to live without a job is terrible. So he finds some young people, and he tries to convince God that these young people are the new Adam and Eve. God still gets to wipe out humanity. It’s a comedy.”