For better or worse, Terry Gilliam is obsessed with the past. It’s not exactly clear where these thematic fixations came from — the man was born in Minnesota and spent his teenage years in Los Angeles, far from Europe and the history of its land — but it’s clear to see when they might’ve formed. Gilliam moved to England in the 60s, where he soon met his Monty Python collaborators Terry Jones, Michael Palin, and Eric Idle. He might be most well-known for his comedies made with his three co-creators, but Gilliam never restricted himself to sketch comedy. In fact, Gilliam has touched on almost every genre imaginable in the years since Monty Python’s heyday. One thing remains constant, though: When he touches on another genre, he almost always combines it with his one true love—fantasy. It’s the best word to describe Gilliam’s best work. Fantastic, or imaginative in the truest sense.
Brazil
Terry Gilliam’s 1985 science fiction dystopia features some great performances by Robert De Niro and Jonathan Pryce, but the thing that’s the most effective about Brazil is its biting satire of consumerism and man’s reliance on technology. Gilliam might be slightly obsessed with the history of the past, but he seems to have a keen eye for what the future might look like, as well. Brazil is Gilliam at his most competent.
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Time Bandits
What a gem Time Bandits is — wholly original while also managing to remain rooted in history, the film features a cast of little people and a young boy as they try to maneuver their way through history with a stolen map of time and space. They’re in search of time’s greatest treasures, and they refuse to be confined by the constraints of the present. It’s both highbrow and lowbrow, both lighthearted and dark, a fairytale and an original creation all at the same time.
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12 Monkeys
Starring Bruce Willis, Madeleine Stowe, and Brad Pitt, Gilliam’s 12 Monkeys is based on Chris Marker’s classic short film La Jetée. Like that original short, 12 Monkeys is a creepy and unsettling look at the world after being ravished by war and disease. Gilliam manages to keep things tense and unexpected, utilizing each cast member to the best of their abilities and resisting science fiction tropes with relative ease.
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Monty Python and the Holy Grail
What more can be said about Monty Python and the Holy Grail that hasn’t already been said? It’s so hard to place on a list, so hard to think of critically, so hard to analyze in any real way because of its timeless nature and its brilliant comedy. Whether this movie is actually any “good” doesn’t matter — Monty Python and the Holy Grail is as influential and as seminal as a 20th-century comedy can be.
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The Fisher King
Starring Robin Williams and Jeff Bridges at the top of each of their respective games, Gilliam’s The Fisher King is a modern day fairy tale about love, life, and the consequences of our actions. It’s a compelling story, one that isn’t afraid to face brutally honest truths about reality and what it means to be human. The movie managed to score five Oscar nominations and one win, cementing the film’s status as one of Gilliam’s best.
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Fear and Loathing in Las Vegas
Hunter S. Thompson is one of the most controversial writers of the 20th century. Who better to capture the eccentricity of Thompson’s most iconic work than Terry Gilliam, someone who could be described as just as controversial and eccentric? The movie was initially met with mixed reviews, but it has since received plenty of praise as viewers revisit the film decades after its release. Benicio Del Toro has always been captivating in any role, and his character Dr. Gonzo is no exception.
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Monty Python’s Meaning of Life
The third film that the Monty Python crew collaborated on, Meaning of Life explores human existence from birth to death to the afterlife in search of an answer to life’s most pertinent question. Gilliam shares directorial duties here with Terry Jones, director of the second Monty Python film Life of Brian, and the two prove to be excellent collaborators off-screen as well as in front of the camera. It’s the last moviegoers saw of the Monty Python crew for a while, but it proves to be a worthy sendoff.
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The Adventures of Baron Munchausen
Based on the many German fables revolving around 18th-century nobleman Baron Munchausen and his escapades throughout the Ottoman Empire, Terry Gilliam’s 1988 film reunites some of the Monty Python gang with other A-list actors to create something wholly original. The movie was an absolute bomb at the box office, grossing less than a fifth of its nearly 50 million dollar budget, but it’s no matter — the movie is thoroughly enjoyable for any fan of Gilliam’s work.
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Jabberwocky
Gilliam’s family-friendly fantasy-adventure Jabberwocky is something classically his own. It’s almost as if someone put a bunch of Gilliam tropes into a generator and this is what it came up with. Jabberwocky isn’t for everyone, but Gilliam’s first directorial effort is certainly deserving of recognition for its daring and unique take on a classic poem by Lewis Carroll.
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The Imaginarium of Doctor Parnassus
An important aspect of Gilliam’s career is the fact that he is hopelessly devoted to his own passion projects. Recently, for example, he’s battled court case after court case in an attempt to make The Man Who Killed Don Quixote. Back in 2009, he faced similar roadblocks with The Imaginarium of Doctor Parnassus. After the death of Heath Ledger, the original lead in the film, Gilliam was forced to get creative. He ended up casting three actors in Ledger’s place in order to finish the film, which was only one-third of the way complete at the time. The end result is probably not what Gilliam had in mind, but it’s impressive nonetheless.
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