Best Terry Gilliam Movies, Ranked for Filmmakers - Featured

There’s no denying that Terry Gilliam’s films have left an indelible imprint on the landscape of cinema. Gilliam got his start as a cartoonist in L.A. before joining the Monty Python. While with the Pythons, Gilliam worked as an animator, writer, director, and actor. After the group went their separate ways in the early 1980s, Gilliam began directing his own films. We’re going to rank the best Terry Gilliam movies from both his time with the Pythons and on his own. Each film on this list is a feature either written or directed by Terry Gilliam.

Surrealism Meets Trauma

15. Tideland

Tideland  •  Trailer

Tideland is the most contentious film Gilliam’s made. Most critics are in agreement that the film is lacking in purpose, refinement, and visual tone but some have lauded Gilliam’s direction and the film’s production design. There’s a bit of gold hidden in the plot of Tideland, but for most, excavating it from a near-obsidian exterior isn’t worth the effort.

Terry Gilliam Films

Conclusion

Tideland tries to visually articulate childhood trauma, but struggles with poor cinematography and an uneven plot.

Too Good to be True

14. The Brothers Grimm

The Brothers Grimm  •  Trailer

Terry Gilliam adds his signature visual flair to this fictitious story based on the Brothers Grimm. The marriage between Gilliam and the brothers Grimm fairy tales seems too good to be true — and sadly, it was.

Gilliam’s The Brothers Grimm is not about the fairytales we all know, such as Snow White and Hansel and Gretel, it’s about a fictional time period where the brothers were con-artists not writers. The whole plot is muddled to the point of confusion and never quite gets off the ground.   

Full Terry Gilliam Filmography

Conclusion

The Brothers Grimm does little to satisfy fairytale fans or fans of Gilliam — ultimately making poor use of a marriage that had so much potential.

Existential Sci-Fi

13. The Zero Theorem

The Zero Theorem  •  Behind the Scenes Special

The Zero Theorem is widely believed to be a spiritual successor to Brazil. Both are nightmares of absurdist dystopias, and both involve men on the outside, hoping to break free of them. And it did make our list of the best cyberpunk movies of all time.

But whereas Brazil is rich in subtext, detail, and sharp comedy, The Zero Theorem is lacking. It’s a disappointment that the story in The Zero Theorem is delivered in such a heavy-handed way because there are nuggets of greatness within it.

Terry Gilliam Films

Conclusion

With a script expanded seemingly just to make it feature length, The Zero Theorem was arguably doomed before it ever began.

Homage to Imagination

12. The Imaginarium of Dr. Parnassus

The Imaginarium of Dr. Parnassus  •  Behind the Scenes

Featuring an all-star cast of Johnny Depp, Jude Law, Colin Farrell, Christopher Plummer, Tom Waits, and the late, great Heath Ledger who died during filming, The Imaginarium of Dr. Parnassus is a complex story of fantasy across worlds.

The story of making the film may be more interesting than the film itself, but fans of Gilliam are sure to find some things to like in The Imaginarium of Dr. Parnassus’ two-hour runtime.

Best Terry Gilliam Movies

Conclusion

It’s impossible to know how the original The Imaginarium of Dr. Parnassus would’ve turned out, but in the end, it’s almost become more of a love letter to Ledger than anything else.

Absurdist Period Piece

11. Jabberwocky

Jabberwocky  •  Restoration Clip

For anyone familiar with Lewis Carrol’s nonsense poem of the same name, Jabberwocky is sure to rile up some good laughs and even a quick thrill. Although Gilliam had directed films before, Jabberwocky was his first solo feature.

Jabberwocky doesn’t quite live up to the standard of Gilliam’s best period piece comedies with the Pythons, but it’s not half-bad either.

Terry Gilliam Filmography

Conclusion

As the genre it’s based on implies, Jabberwocky is near complete and utter nonsense — albeit often in a good way.

Lost in La Mancha

10. The Man Who Killed Don Quixote

Terry Gilliam on  •  The Man Who Killed Don Quixote

Billed in its own credits as a film 25 years in the making, The Man Who Killed Don Quixote’s backstory is both a blessing and a curse. Few films other than Apocalypse Now had such a nightmarish production. Gilliam tried to make The Man Who Killed Don Quixote three separate times, but was thwarted by various technical, personal, and environmental issues. Johnny Depp, Ewan McGregor, John Hurt, Robert Duvall were all once attached to the project, but none returned to act in its final shoot. Instead, Adam Driver and Jonathan Pryce took the leading roles.

Before release, plenty of people were saying “Okay the story of this film is crazy, but is it any good?” I’d say the answer to that question is “it’s okay.” There’s no doubt about it, The Man Who Killed Don Quixote is a visual treat, but the same can’t be said for its story — which is mumbled, jumbled, and fumbled throughout.

Best Terry Gilliam Movies

Conclusion

In the end, many wanted to see something great in The Man Who Killed Don Quixote that simply wasn’t there.

Fear and Loathing in Las Vegas  •  Video Essay

Based on the renowned novel of the same name by Hunter S. Thompson, Fear and Loathing in Las Vegas is a hallucinogenic fever-dream of two men’s journey into the infamous casino city.

Fear and Loathing in Las Vegas is weird. I mean real weird. It’s not for the faint of heart, nor those who are uncomfortable with gratuitous drug use. But if you look past its hedonistic exterior, you’ll find one of the best dark comedies and a deep commentary on the trials and travails of the American dream. 

Terry Gilliam Films

Conclusion

Fear and Loathing in Las Vegas may not be one of the best Terry Gilliam movies but it’s surely one of the most iconic.

What’s the Purpose?

8. Monty Python’s The Meaning of Life

The Meaning of Life  •  Galaxy Song

The Meaning of Life is, as the title implies, a commentary on the meaning of life. For fans of the Python’s other works, much of their signature wit and humor can be found here.

However, without the narrative focus that binds together Holy Grail and Life of Brian, things never quite come completely together.

Did You Know?

Although Gilliam only directed small portions of the film, he’s widely credited as a co-director for Monty Python’s The Meaning of Life.

Python’s/Best Terry Gilliam Movies 

Conclusion

Although not the Pythons best work, The Meaning of Life often finds them at their most unrestrained.

Sweeping Fantasy Adventure

7. Adventures of Baron Munchausen

The Adventures of Baron Munchausen  •  Making of

Often cited as one of the best Terry Gilliam movies, The Adventures of Baron Munchausen is a big, bold, adventure through time and space. The film stars John Neville in the title role and features Uma Thurman, Eric Idle, Jonathan Pryce, and more in supporting roles.

Stories of the film’s arduous production have become infamous in cinema circles. The Adventures of Baron Munchausen went way over budget, which drew considerable ire from studio execs. As a result, very few copies were circulated for release.

Terry Gilliam Filmography

Conclusion

In the end, The Adventures of Baron Munchausen overcame its own commercial failure to garner a massive cult-following.

Around the World

6. Time Bandits

Time Bandits  •  Trailer

Terry Gilliam’s first hit as a solo director Time Bandits is full of action, adventure, and most importantly, spirit. Gilliam collaborated with various Python alums (Palin and Cleese) for the film.

Time Bandits sees Gilliam at his fantastical best, mixing whimsy and morals to create a type of fairytale unlike any other.

Best Terry Gilliam Movies Ranked

Conclusion

Time Bandits isn’t perfect but it’s a great fantasy film for audiences of all ages.

In Pursuit of an Artifact

5. Monty Python and the Holy Grail

What the Holy Grail Teaches us About Filmmaking

There’s low budget filmmaking and then there’s no budget filmmaking. It could certainly be said that Monty Python and the Holy Grail falls into the latter camp. Although the Holy Grail had a budget in excess of $200,000 ($1 million adjusted for inflation), film-stock and location shooting was much more expensive then than it is today.

As such, each day of shooting threatened to push the production over budget. This led to one of the more surprising, yet unforgettable endings in cinema history and one of the best comedies ever.

Terry Gilliam Movies List

Conclusion

Co-directed by Terry Jones, Monty Python and the Holy Grail is the film that put the Pythons on the map internationally, and it also labeled Gilliam as an up-and-coming director.

Another Pursuit of the Holy Grail

4. The Fisher King

Making of  •  The Fisher King

The Fisher King, although certainly sensational, finds director Terry Gilliam at his most grounded. Perhaps one reason for this groundedness is the subject of the film, which follows an alcoholic former radio host dealing with the phantom guilt of indirectly inspiring a mass-shooting.

Jeff Bridges stars in the film alongside Robin Williams and Mercedes Ruehl, the latter of which won an Academy Award for her performance.

Terry Gilliam Movies Ranked

Conclusion

The Fisher King is one of the best Terry Gilliam movies and stands out against most of his other work.

Time Travel Done Right

3. Twelve Monkeys

12 Monkeys  •  Trailer

One of the best sci-fi movies of all time, Twelve Monkeys makes great use of some stellar performances from Bruce Willis, Brad Pitt, and Madeleine Stowe.

This is one of Brad Pitt's best, and his performance as wacko Jeffrey Goines landed him a nomination for Best Supporting Actor. Gilliam directs Twelve Monkeys with his signature blend of the fantastical and the grounded. But with this film, Gilliam found a rare balance between the two which resulted in one of his very best works.

Best Terry Gilliam Movies

Conclusion

Twelve Monkeys is a nuanced tale of time travel and fate across a virus-stricken America.

Dystopia Like None Other

2. Brazil

What is Brazil?  •  Making of Documentary

How does one begin to understand Brazil? The fourth directorial feature from Gilliam, widely referred to as his magnum opus, is bold, brash, intimate, expansive, and every which, where, when in between.

Perhaps the best way to understand Brazil is to look at its inspiration, George Orwell’s 1984. But whereas Orwell’s story is uber-dramatic, Gilliam’s is much more farcical. Both stories share considerable similarities though, such as a focus on totalitarianism, the death of individuality, and an unfair sense of consequentialism.

Greatest Terry Gilliam Films

Conclusion

Brazil sees Gilliam at his filmmaking best, using production design to mix whimsical fantasy with the horrors of corruption.

Always Look on the Bright Side

1. Monty Python’s Life of Brian

Dogma and Theology  •  Life of Brian

Few films are more irreverent than Monty Python’s Life of Brian. Python member Graham Chapman stars in the picture as Brian, a man born the same night as Jesus in the stable next door. Through comedic escapades and religious fanaticism, the people of Judea start to think of Brian as the true Messiah.

As far as comedies go, Life of Brian is as good as it gets. The film is even better than Holy Grail due to sharper writing, more refined focus, and better production design. Although Life of Brian has its detractors, particularly higher-ups in the Catholic church. But anyone who knows that cinema is meant to push, pull, and satirize will find a lot to love.

Best Terry Gilliam Movies

Conclusion

Gilliam relinquished his co-directing duties but still served as a co-writer, set designer, and animator for the all-time masterpiece Life of Brian.

UP NEXT

The best Tim Burton movies

Fans of Terry Gilliam know his works for their distinct, instantly recognizable style. Fans of Tim Burton know his works for the same reason. In this next article, we look at Tim Burton’s entire filmography and rank them top to bottom. You may be surprised to see which film gets the top honor!

Up Next: Burton's Best →
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