Some movies feel somewhat generic and could have been directed by anyone, but you always know when you’re watching a film directed by Terry Gilliam. His work has a distinct style and a dedicated following. It’s sometimes funny, occasionally disturbing, but always quirky.

Maybe you’re a Monty Python fan looking for movies in a similar genre or a curious movie buff looking for something new. Either way, other fans have visited the IMDb and rated their favorite Tery Gilliam movies, creating a handy list to get you started.

10 Tideland – 6.5

A twisted tale that blurs the line between reality, fantasy, comedy and tragedy, Tideland is the story of an abandoned child.

The story reserves any judgment or moral lessons and instead focuses on the experience of Jeliza-Rose, the main character. It’s a version of Alice in Wonderland that some find fascinating and others, deeply disturbing.

9 The Imaginarium Of Doctor Parnassus – 6.8

This is more than a quirky story of a group of traveling performers who also seem to have supernatural powers. The Imaginarium of Doctor Parnassus is a classic retelling of the story of a man, the Devil, and a battle of wits.

For those who are fans of Heath Ledger, this was his last film, and the end credits are entitled, “A Film from Heath Ledger & Friends.”

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8 Time Bandits – 6.5

Time Bandits is one of those classic 1980s favorites that stood out with other sci-fi comedy crossovers of the same era, like Back to the Future and Star Trek IV: The Voyage Home. It’s fondly remembered for its brilliant storytelling and star-studded cast.

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Both John Cleese and Sean Connery make appearances in this fight against Evil disguised as a botched robbery and a few accidental trips through space and time. The lesson learned here is that maybe it’s better to listen to your kids and stop romanticizing history.

7 The Adventures Of Baron Munchausen – 7.2

Dreams, fairytales, reality, and fantasy all gel together in this collection of wacky adventures starring Baron Munchausen and some of his closest friends.

The movie seems to focus on defending a city from an invasion of Turks, but things are never as they appear when the Baron is telling the story. But is it only a story? Or did all of this really happen?

6 The Fisher King – 7.5

Like other Terry Gilliam movies, this one blurs the line between reality and fantasy in ways that are both funny and tragic. The Fisher King has some poignant things to say about how society handles mental illness, poverty, celebrity, and media portrayals of all of the above.

The medieval segway in the setting of modern New York is a unique juxtaposition and stars Robin Williams and Jeff Bridges are at the peak of their careers.

5 The Meaning Of Life – 7.6

A fan favorite that’s also a highly-rated Monty Python film, The Meaning of Life is a series of skits held together by a central theme, the meaning of life. Terry Gilliam works with his original crew, Monty Python, and they literally go from birth to death looking for an answer.

The tone goes from satirical to nihilistic to absurd, toying with everything from organ donation to the plight of workers in the service industry and the dangers of salmon mousse. In the end, Mr. Death comes by about the reaping, because doesn’t he always?

4 Fear And Loathing In Las Vegas – 7.6

This could be Gilliam’s most notorious and well-known film. An adaptation of the Hunter S. Thompson novel of the same name, Fear and Loathing in Las vegas chronicles a time in America that no longer exists and never will again.

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Johnny Depp is amazing as Hunter S., so much so that even the famous author complimented him, and Benicio del Toro steals every scene in which he appears.

3 Brazil – 7.9

Brazil is one of Gilliam’s more chilling films, exploring the banality of evil and the lack of humanity inherent in any authoritarian state.

Paperwork turns society into a dystopian nightmare, and all it takes is a typo to destroy several innocent lives. Unlike other Terry Gilliam movies, this one blurs reality and fantasy only to a point, revealing a stark and horrific reality at the very end.

2 12 Monkeys – 8.0

Most movie fans today know Terry Gilliam through 12 Monkeys. It had a higher budget and better publicity than his other movies, and it features big names like Brad Pitt and Bruce Willis.

The story is about a plague and time travel, and instead of a dream or fantasy, it’s all real. The movie creeping and unsettling, but it’s more coherent than a typical Gilliam flick, with plenty of Dutch angles to put the viewer off balance.

1 Monty Python And The Holy Grail – 8.2

It’s not a surprise that the most highly rated Gilliam movie would also be one of the best-loved Monty Python and John Cleese movies. The low budget of Monty Python and the Holy Grail actually adds to the surreal charm and prompted some of the movie’s more iconic jokes.

For example, there aren’t any horses in the movie because it would have been too expensive to hire them. The substitute is Patsy the Squire following King Arthur while banging two coconut husks together.

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Kristy Ambrose
(159 Articles Published)

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Kristy Ambrose has been writing professionally since 2010. She dabbles in various genres, including everything from short blog posts to serialized novels. Her inspiration comes from gamers, beachcombers, foodies and of course her fellow travelers. She holds a Bachelor of Arts in English literature from the University of Victoria.

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