Terry Gilliam is the type of director who makes the impossible happen. A harmless-looking rabbit can turn out to be a vicious, man-eating monster able to beat the Knights of the Round Table. 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.
It's this spirit of surrealism that defines Gilliam and his films, emboldening them with a spirit that anything and everything is possible. His movies are filled with imagination, bursting with creative ideas, characters, dialogue, and imagery the likes of which audiences had rarely seen before or since.
Best Terry Gilliam Movies and Where to Stream Them
Initially, a cartoonist and animator, Gilliam’s success came later in the 1960s’, when he joined the now-iconic comedy troupe, Monty Python, as their lead animator. As a member of Python, Gilliam's animation helped define the troupe's absurd comedic style, bridging sketches and blending animation into a live-action sketch (something that would later carry over into many of Gilliam’s most famous films).
After Python's unofficial disbandment, Gilliam combined the absurdist sense of humor he'd developed from the troupe with his love for strange imagery and social criticism into his directorial career, creating some of the most unique, innovative films of his day.
With Gilliam set to turn 80 on November 22, we thought we'd take a look back at some of his most groundbreaking feature-length films, ranking his 10 best movies, and providing information about where they are currently streaming.
In many ways, 12 Monkeys feels like the movie that has the least amount of Gilliam's signature style. It's easy to see something like Brazil or Time Bandits and go “Oh, yeah, that's a Gilliam film, all right,” but with 12 Monkeys it could have been just as easily directed by any director from the '90s.
Set in the near future, the world has been 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, eventually tracing it back to an unstable environmental terrorist (Brad Pitt).
Far and away Gilliam's highest grossest film of his career, it's the movie that 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 with some scenes—the entire post-apocalyptic future is dripping with Gilliam's artistic design and penchant for strange, dystopian imagery—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.
Don't get us wrong, it’s certainly not a bad or unremarkable movie by any means. But it lacks the same charm and distinct vision as Gilliam's other projects, hence it's low rating on his list.
Streaming on HBO Max
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 finds himself the unwitting hero of the people, sent to battle a fearsome monster plaguing the countryside.
In its subject matter and tone, Jabberwocky feels more as much 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 notably less nonsense sense of humor as Holy Grail. (There's no ending where our heroes are suddenly arrested by modern-day bobbies, but when a character is hit, they literally go flying across the room, with the fate of the kingdom decided on a game of hide and seek.)
Additionally, while Holy Grail does a good job satirizing Arthurian legend, Jabberwocky 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 completely 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 and the more satirical themes of his later films. Many of the elements Gilliam would later explore more fully in later films are all there—the social criticism of class and power, where idiots are still in charge—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.
Streaming on Prime Video
The Imaginarium of Doctor Parnassus
From the onset of the 2000s', Gilliam hit a slight career slump. In 1998, after nine years of setbacks,he finally secured funding for his dream project, The Man Who Killed Don Quixote, only to see the movie fall apart due to numerous production issues.
From 2003 to 2016, Gilliam made several attempts to relaunch the project, with each one ending in failure. His ambition and enthusiasm for Don Quixote may have unfortunately stalled Gilliam artistically during those years, 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 was likely his 2009 project, The Imaginarium of Doctor Parnassus, a return to form of sorts for Gilliam to the surreal ventures he had built his career making.
A struggling traveling theatrical troupe led by the magician, Doctor Parnassus (Christopher Plummer), finds a disgraced philanthropist named Tony (Heath Ledger) hanging under a bridge by his neck. After rescuing him, 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 a remarkably entertaining story, with plenty of clever twists, mystery, and fantastic visuals (a highlight of any of Gilliam's films). Unfortunately, the film marked the death of Ledger halfway through filming, but the director ingeniously managed to film around this by casting Johnny Depp, Jude Law, and Colin Farrell as an alternative, “transformed” versions of Tony, who changes when he steps inside Doctor Parnassus’s otherworldly Imaginarium.
The film can be upsetting knowing it's Ledger's final posthumous release, but Doctor Parnassus still remains one of the best, most original films in Gilliam's entire career, and certainly one of his best since the turn of the century.
Streaming on Tubi
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 in his 2018 film—yet he'd never fully 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 equally unstable attorney, Dr. Gonzo (Benicio del Toro). Together, the two embark on a series of drug-fueled misadventures as they explore their chaotic Sin City setting.
On the surface, you wouldn't necessarily think such a drug-centric book about two oddball characters prone to fits of violence would be up Gilliam's wheelhouse—given the subject, setting, and his past filmography, someone like Martin Scorsese may have been a more ideal choice for director)
However, with how off-the-walls 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. Gilliam was perfectly able to translate the hellish landscape and already off-kilter nature of both Las Vegas and Thompson's original book onto the screen, managing to retain Thompson’s already chaotic scenes, characters, and setting and blend it with his signature unusual style of filmmaking.
A box office bomb upon release, Fear and Loathing has since gone on to achieve cult status among more contemporary moviegoing audiences today.
Streaming on Peacock
The Fisher King
Following his career-high in the 1980s, Gilliam began the '90s with an equally fantastical work that saw him return to Arthurian legend with the comedic drama film, 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 making Quixote, the similarities may not be so incidental.)
Both films feature a narcissistic but successful character (Bridges in this film, Adam Driver in Quixote) in show business who face a crisis that halts their career, and who eventually 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 makes 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 wonderfully humane and heartfelt depiction of New York City's homeless, with the rich, successful Yuppies frequently appearing unhappy or capable of incredible cruelty in their treatment of the homeless, and the homeless themselves being their moral and ethical superiors in every way.
Not currently streaming, but available to rent online
Critically, commercially, and artistically, Gilliam hit his ultimate career-high throughout the 1980s', producing some of his best and most warmly-received films. The first film that began this newfound period of success for Gilliam was his 1981 adventure fantasy film, Time Bandits.
Imaginative eleven-year-old Kevin (Craig Warnock) is frequently 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 find themselves on an adventure across numerous time periods and encounter numerous historical and mythical figures, including the height-obsessed Napoleon (Ian Holm), an airheaded 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 endlessly enjoyable characters and humor. 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—all of which feature characters who use their imagination to free themselves from repressive authority figures—Time Bandits was critically praised upon its release, earning favorable comparisons to the work of Roald Dahl for its humor, originality, and offbeat, dark ending.
Streaming on HBO Max
The Man Who Killed Don Quixote
Gilliam's passion project that he'd been trying to make since 1989, the road Gilliam took to make this film a reality was one filled with numerous setbacks and challenges. (To learn more about the specifics, we recommend watching the documentaries Lost in La Mancha and He Dreams of Giants).
In 2018, after nearly 30 years of production that saw cast and crew members come and go—including Johnny Depp, Ewan McGregor, Robin Williams, Robert Duvall, Michael Palin, and John Hurt—Gilliam finally got his dream project off the ground, intending it to be his long-awaited, ultimate masterpiece.
Toby Grummett (Adam Driver) is a brilliant but extremely vain director filming a commercial in Spain. Once an idealistic, aspiring young filmmaker, he has achieved success, wealth, and acclaim, but finds he still isn't creatively or emotionally satisfied. 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 actually Don Quixote and mistakes Toby for his loyal squire, Sauncho Paza.
Looking at Gilliam's past filmography, you almost get the sense 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, especially). 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 (not wanting to resume his life as a lowly, lonely shoemaker after Toby's film, he takes up the mantle as the legendary Don).
All in all, Gilliam's Quixote may not be the finest film he's ever released, but it is gratifying knowing Gilliam managed to finally fulfill his dream of finishing his project—something he's been building towards for 30 years—and still manages to be incredibly entertaining in its own right.
Streaming on Hulu
The Adventures of Baron Munchausen
The third and final film in Gilliam's “Imagination” trilogy, The Adventures of Munchausen was also Gilliam's last film of the '80s, a decade he appeared to be at the top of his game. Like the two prior entries in the trilogy, it's a movie packed with overwhelming creativity, focusing on an individual who escapes from an oppressive, rule-based society and flees on an incredible journey populated by numerous odd characters and settings.
Loosely based on the stories of Baron Munchausen (a fictional 18th-century nobleman in German folklore), an unnamed European city faces unending bombardment while under siege by the Ottoman Empire. Their only hope of survival rests with the titular Baron (John Neville)—now an old man—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.
In style and tone, Baron Munchausen bears a serious resemblance to Time Bandits, Gilliam's earlier “Imagination” film, especially in its more light-hearted, whimsical story.
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 stalked by the Angel of the Death, from a bygone era of fantasy that has no place in this “Age of Reason” he finds himself in.
For a family-friendly movie, it has its share of sadness and sentimentality, but is also rich in 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.
Gilliam's final film of the '80s marked the end of a peak phase in Gilliam's career, concluding the decade on an otherwise extremely high note.
Not currently streaming, but available to rent online
Monty Python and the Holy Grail
Perhaps the most frequently quoted movie in existence, there's a reason people still talk about Holy Grail nearly 50 years after its release. It remains an indigenously made, ceaselessly entertaining movie that audiences worldwide have enjoyed from generation to generation. 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 best. It's a movie full of side-splitting meta-humor that has managed to stay as fresh and funny today as it did over four decades ago on its release, as well as remaining one of the most well-known, iconic comedy films of all time.
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 would assume 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 work carried over from Flying Circus predominantly featured in Holy Grail.
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, as well as its numerous iconic punchlines and jokes.
Streaming on Netflix
If you've seen every one of Gilliam's movies, you know without a definitive doubt that Brazil is easily his crowning achievement. Smart, funny, innovative, and equally dreamlike and nightmarish, it's Gilliam's quintessential masterpiece, a film that illustrates all of his artistics interests and stylistic sensibilities, serving as the ultimate film that is most fully and distinctly his own and that literally no one else could've made.
In a vaguely defined 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 who frequently appears in his dreams (Kim Greist), Sam wades through his oppressive world in an effort to find her.
Harking back to the dystopian works of Huxley, Kafka, and Orwell (Gilliam originally wanted the title to be 1984 ½), 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—not to mention any one of Sam's wondrously-designed dream sequences.
In this film, Gilliam takes aim at everything from technology, capitalism, and the corporate workplace to fascism and hyper-surveillance, and does so effectively and successfully in every aspect. Not to mention he works with his most skilled cast yet, all of whom play some of the most interesting characters of their careers, including Pryce’s dreamy Sam, Robert de Niro’s mysterious renegade plumber/freedom fighter, and Michael Palin’s charming family man/sociopathic government torturer.
It's a brilliant example of a satirical work, and though it may have underperformed initially upon its release in 1985, it has since gone on to achieve extreme acclaim in subsequent years, with critics rightfully praising Brazil as Gilliam's greatest film to date.
Streaming on Tubi
For over 50 years, Gilliam's films have managed to impress and awe inspire audiences across the globe, focusing on heroes young at heart and struggling to live in near dystopian settings. His movies explore the importance of imagination, as well as frequently satirizing bureaucracy and authoritarian-based figures, a prevalent theme throughout his body of work.
Since his start as an animator and member of Monty Python, Gilliam has continued to impress and inspire a whole generation of moviegoers, influencing the work of South Park co-creators Trey Parker and Matt Stone, Rian Johnson, Edgar Wright, Guillermo del Toro, and many, many others.
Given Gilliam's most recent films, it's doubtful that either he or his highly unique artistic vision will slow down even as the director approaches 80, and like everyone, we look forward to seeing what new heights the great director will climb to next.
Richard Chachowski is a freelance writer based in New Jersey. He loves reading, his dog Tootsie, and pretty much every movie to ever exist (especially Star Wars).