Director Terry Gilliam makes the impossible happen. A harmless-looking rabbit can turn into a vicious, man-eating monster. A group of time-traveling dwarves could burst out of a child's bedroom closet while being pursued by a God-like Supreme Being. An 18th-century folkloric German nobleman could waltz with the goddess Venus through the clouds.
That spirit of surrealism defines Gilliam and his films, emboldening them with a feeling that anything and everything is possible. His movies explode with imagination, bursting with creative ideas, characters, dialogue, and imagery the likes of which audiences have seldom seen before or since.
With how many fantastic films Gilliam has made over the years, we thought it only fitting to explore his dense filmography, ranking every Terry Gilliam movie from best to worst.
In a dystopian future, Sam Lowry (Jonathan Pryce) is a low-ranking, unambitious office drone prone to daydreaming as a form of escape. After seeing a woman in his dreams (Kim Greist), Sam wades through his oppressive world in an effort to locate her.
Harking back to the dystopian works of Huxley, Kafka, and Orwell, and the absurdist style of Monty Python, Vonnegut, and Fellini, Gilliam put everything he had into this film, a triumphant feat of creativity, as seen with the surreal setting, costumes, characters, and story.
In this film, Gilliam takes aim at everything from technology, capitalism, and the corporate workplace to fascism and hyper-surveillance. It's a brilliant example of a satirical work, and though it may have underperformed upon its release in 1985, it has since gone on to achieve extreme acclaim in subsequent years, with critics rightfully praising Brazil as the best Terry Gilliam movie.
2. Monty Python and the Holy Grail
Perhaps the most quoted movie in existence, there's a reason people still talk about Holy Grail 50 years after its release. It's clever, sharp, sarcastic, and provides non-stop laughs throughout — all traits you would expect to find in a Monty Python project, and certainly on display here.
Set in the Middle Ages, King Arthur (Graham Chapman) recruits his Knights of the Round Table to embark on a long, epic quest to find the Holy Grail, encountering numerous obstacles in the form of man-eating rabbits, socialist peasants, insult-hurling French rivals, and the unrelenting, overconfident Black Knight.
In a movie that feels like several Python sketches stitched together through several overarching plot threads, Holy Grail is Monty Python at their peak, full of side-splitting meta-humor and surreal set pieces.
Co-directed by Gilliam with Python member Terry Jones, the movie may feel more like a Python or Jones film than it does a Gilliam project (perhaps it's fitting that Jones assumed solo directorial duties in the two subsequent Python films, Life of Brian and The Meaning of Life). However subtle Gilliam's directorial touch is, his stylistic influence is unmistakable, including scenes that feature his distinct animation carried over from Flying Circus.
Despite his co-directorial status, Holy Grail incidentally remains perhaps Gilliam's most popular work, and one you can't help but enjoy for his light-hearted humor and satirization of Arthurian legend.
3. The Adventures of Baron Munchausen
In the 18th century, an unnamed European city faces unending bombardment while under siege by the Ottoman Empire. Their only hope of survival rests with the titular Baron Munchausen (John Neville), who joins a young girl (Sarah Polley) in an effort to reform his old band of former comrades that takes them on a fantastic odyssey across seas, through mountains, and literally to the moon and back.
Like other Gilliam protagonists (Robin Williams in The Fisher King, Jonathan Pryce in The Man Who Killed Don Quixote), Gilliam manages to portray the otherwise larger-than-life, overly-imaginative Baron as profoundly human — an elderly man a bygone era of fantasy that has no place in this new “Age of Reason” he finds himself in.
For a family-friendly movie, it has its share of sadness and sentimentality but also explodes with Gilliam's signature artistic absurdity, bolstered by a fantastic cast (including the talents of Neville, Pryce, Oliver Reed, Uma Thurman, Robin Williams, and Eric Idle) and impressive visuals that make each scene feel like an 1800s political cartoon.
4. The Man Who Killed Don Quixote
Despite his fame and fortune, advertising director Toby Grummett (Adam Driver) still isn't satisfied from an artistic or personal standpoint. Exploring a nearby village where he filmed his student project — an adaptation of Don Quixote using locals as cast members — Toby meets the old man he cast in the leading role (Jonathan Pryce), who believes he is Don Quixote and mistakes Toby for his loyal squire, Sauncho Paza.
Looking at Gilliam's past filmography, it seems like his passion for The Man Who Killed Don Quixote leaked into his other projects, given the thematic similarities between Quixote and Gilliam's numerous other films throughout the '90s and 2000s' (The Fisher King, Tideland, and Doctor Parnassus). You could also see a strong resemblance between Quixote and Gilliam's beloved “Imagination” trilogy, featuring a character (Pryce's Quixote) who escapes into his own fantasies in order to escape from a sobering, depressing reality.
All in all, Gilliam's Quixote may not be the best Terry Gilliam movie, but it is gratifying to know that Gilliam managed to fulfill his longtime dream of finishing his project — something he'd been working towards for over 30 years.
5. Time Bandits
Imaginative eleven-year-old Kevin (Craig Warnock) lives a life ignored by his idiotic, technology-obsessed parents. Longing for adventure, Kevin joins a band of time-traveling dwarves who stumble out of his closet. Together, the group embarks on an adventure across numerous time periods, encountering numerous figures like the height-obsessed Napoleon (Ian Holm), an air-headed Robin Hood (John Cleese), and the personification of Evil (David Warner).
Written by fellow Python member and frequent collaborator Michael Palin (who also appears in this movie), Time Bandits is Gilliam at his finest — a movie brimming with ingenuity, nonstop action, impressive animation and special effects, and agreeable characters. It has wit, heart, and a story that draws in viewers of every age, as well as containing social critiques touching upon technology and bureaucracy (frequent targets in any Gilliam movie).
The first film in Gilliam's “Imagination” trilogy that would later include Brazil and The Adventures of Munchausen, Time Bandits earned praise upon its release, drawing favorable comparisons to the work of Roald Dahl for its humor, originality, and offbeat, dark ending.
6. The Fisher King
Following his career-high in the 1980s, Gilliam kicked the '90s off with his Arthurian fantasy drama, The Fisher King.
Jack Lucas (Jeff Bridges) is a once-promising, Howard Stern-esque disc jockey who faces a personal and professional crisis when he indirectly causes a tragedy in New York. Years later, as Jack struggles to rebuild his life, he meets a homeless man (Robin Williams) who believes he is a knight on a quest to find the Holy Grail.
With several overarching themes and similarities, The Fisher King feels like a dramatic precursor to Gilliam's later The Man Who Killed Don Quixote. (Since Fisher King is the project Gilliam worked on as he struggled to make Quixote, the similarities may not be so incidental.)
Both films feature a narcissistic but successful character (Bridges in this film, Adam Driver in Quixote) facing a crisis that halts their career, and who encounters someone they influenced in some way to live out medieval fantasies to escape from a somber reality. However similar the two plots are, Gilliam still takes pains to make each film unique in their own way, with The Fisher King blending elements of magical realism, a romantic comedy, and a heist movie all in one, as well as providing social commentary on New York’s class structure.
The movie also offers a humane and heartfelt depiction of New York City's homeless, with the rich, successful Yuppies appearing unhappy or capable of incredible cruelty towards the homeless, the homeless themselves being their moral and ethical superiors in every way.
7. Fear and Loathing in Las Vegas
Gilliam has taken elements and inspiration from several pre-existing sources before — the most obvious being Cervantes's Don Quixote — yet he never adapted a pre-existing work before until his 1998 psychedelic comedy, Fear and Loathing in Las Vegas.
Taken more or less faithfully from Hunter S. Thompson's famous book of the same name, eccentric sports journalist and Thompson stand-in, Raoul Duke (Johnny Depp), travels to Las Vegas to cover an assignment. Joined by his unstable attorney, Dr. Gonzo (Benicio del Toro), the two embark on a series of drug-fueled misadventures as they explore their surroundings.
On the surface, you wouldn't think such a drug-centric book about two oddball characters prone to fits of violence is suitable to Gilliam's talents — given the subject, setting, and his past filmography, someone like Martin Scorsese may have been a more ideal choice for director.
However, given how off-the-wall insane Thompson's two main leads are, Gilliam may have been the perfect choice for adapting such a strange, psychedelic novel for a film adaptation. Translating the hellish landscape and already off-kilter nature of both Las Vegas and Thompson's original book onto the screen, Gilliam managed to to retain Thompson’s chaotic scenes, characters, and setting and blend them with his signature unusual style of filmmaking.
8. The Imaginarium of Doctor Parnassus
From 2003 to 2016, Gilliam made several attempts to launch his dream project, The Man Who Killed Don Quixote, with each effort ending in failure. His ambition and enthusiasm for Don Quixote may have blunted Gilliam's artistic sensibilities during this period, resulting in films (The Brothers Grimm, Tideland, The Zero Theorem) that failed to live up to the esteem of his earlier work.
The best movie from that period remains Gilliam's 2009 project, The Imaginarium of Doctor Parnassus, a return to form and the surreal ventures Gilliam had built his reputation making.
A struggling traveling theatrical troupe led by the magician Doctor Parnassus (Christopher Plummer), rescues a disgraced philanthropist named Tony (Heath Ledger) hanging under a bridge by his neck. Taking him in, Tony joins the troupe in their efforts to collect five souls to save Parnassus's daughter (Lily Cole) from the Devil (a suave, pencil-mustachioed Tom Waits).
The movie itself offers an entertaining enough story, with plenty of clever twists, mystery, and fantastic visuals (a highlight of any of Gilliam's films). It can be upsetting knowing the film contains Ledger's final performance, but Doctor Parnassus still remains one of the best, most original films in Gilliam's entire career, and ranks among his strongest efforts since the turn of the century.
After Monty Python's Flying Circus ended in 1974, the comedy troupe turned their attention towards their individual careers, reforming every so often to collaborate on a project together. In the interim between their first two films (Holy Grail and Life of Brian), Gilliam — like every Python — set out on his own, pursuing a directorial career after meeting success co-directing Holy Grail with Terry Jones.
In Gilliam's solo debut, Jabberwocky, a clueless, innocent young cooper's assistant (Michael Palin) is shunned by his father and relocates to a medieval city. Once there, he becomes the unwilling hero of the townspeople, forced to battle a fearsome monster plaguing the countryside.
In its subject matter and tone, Jabberwocky feels more as much like a Python film as a Gilliam movie, complete with appearances by Python members and frequent collaborators like Terry Jones, Neil Innes, and of course, Palin. Though the Dark Age setting is reminiscent of Holy Grail, the movie looks different and has a less nonsensical sense of humor as Holy Grail.
While Holy Grail does a good job satirizing Arthurian legend, Jabberwocky also seems more concerned with portraying the more realistic, grimy aspects of living in the Dark Ages — with characters having brown teeth, defecating and urinating out windows, and everyone (including the King) appearing unkempt filthy.
In numerous ways, Jabberwocky feels like an important bridge in Gilliam's career, a stepping stone from the lighthearted humor of his Monty Python days into the more satirical thematic territory of his later films. Many of the elements Gilliam later explored are all there — the social criticism of class and power — and though it may not be as funny or have the same magical realism as Gilliam's later work, it remains an interesting enough debut effort.
10. 12 Monkeys
In the near future, the world will be devastated by a man-made virus that has wiped out most of the human population, forcing the survivors to live underground. As part of his parole, a prisoner (Bruce Willis) is assigned to go back in time to 1996 to collect information about how the virus began, tracing it back to an unstable environmental terrorist (Brad Pitt).
Far and away Gilliam's highest-grossing film of his career, 12 Monkeys feels like it would have the most audience appeal, riffing on the popularity of time travel post-Terminator and combining with it some of Gilliam's favorite themes (authoritarianism, ravaged natural ecosystems, and individuals struggling to live under bureaucratic societies).
Gilliam's imagination shines through in some scenes — the entire post-apocalyptic future is dripping with Gilliam's artistic design — but for the most part, this seems like the kind of movie a director makes that he knows will be a commercial success and that he's able to capitalize on for future projects. It’s not a bad or unremarkable movie by any means, but it lacks the same charm and distinct vision as Gilliam's other projects, hence its low rating on his list.
Say what you will about Terry Gilliam and his work, but even the harshest critics can admit that each of his films burst with creativity. In spite of his film’s imaginative quality and unique direction, however, not all of them result in altogether fantastic films, with Gilliam’s 2005 film, Tideland, being a perfect example of this.
Abandoned by her family, a precocious young girl (Jodelle Ferland) survives on her own in an abandoned Texas mansion, escaping her grim reality by venturing into her vivid imagination.
Though possessing the same vivid artistry and sense of imagination as Gilliam’s other films, Tideland buckles under the weight of Gilliam’s abundant themes (mental health, familial relationships, and substance abuse, among others). Overstuffed and overlong, it’s a film where Gilliam could’ve done more with less, cutting the runtime down to a manageable hour and a half and still retaining the Alice in Wonderland-esque atmosphere he tries so hard to establish.
12. The Brothers Grimm
Gilliam’s most underwhelming film, The Brothers Grimm is little more than a sensationalized monster film bearing little of Gilliam’s signature imagination. Try as he might to establish a magical tone, Gilliam’s lack of charm is apparent in The Brothers Grimm, which is about as hollow and empty a film as Hansel and Gretel: Witch Hunters or 2011’s Red Riding Hood.
Having made their career as supposed “monster hunters,” the sibling con artists known as the Brothers Grimm (Matt Damon and Heath Ledger) must combat a mysterious creature responsible for kidnapping dozens of children.
At first glance, The Brothers Grimm seems like a suitable premise for Gilliam’s strengths as a director. While the movie could’ve been a fantasy epic on par with Guillermo del Toro’s Pan’s Labyrinth, the resulting film relied on too many conventions and cliches, establishing itself as one of Gilliam’s most underwhelming films to date.
13. The Zero Theorem
In 2013, Gilliam concluded his unofficial trilogy of films with The Zero Theorem, completing Gilliam’s dystopian series starting with Brazil and continuing with 12 Monkeys (known as the “Orwellian triptych”). Compared to the trilogy’s earlier installments, however, The Zero Theorem can be seen as a disappointing final chapter in Gilliam’s loosely connected sci-fi saga.
In a dystopian future, a lone computer scientist (Christoph Waltz) attempts to decipher a difficult mathematical formula to determine whether life holds any meaning or not.
Posing a variety of introspective questions, The Zero Theorem retains the same philosophical themes and quirky atmosphere as Gilliam’s earlier films. For all its originality, the movie does little to set itself apart from Gilliam’s much more engaging films from the first half of his career.