Uma Thurman Baron Munchausen naked clamshell

Terry Gilliam was always the odd man out in Monty Python — he was the only American, he wasn’t Oxbridge educated, and he was an animator, not a comedy writer. He did, however, find his directing feet with the troupe, co-directing "Monty Python and the Holy Grail." He would also go on to cast Michael Palin and Eric Idle in many of his projects.

In Gilliam’s first "solo" film, "Jabberwocky," the Python influence was clear, but it would become less so as he branched further into flights of fancy and dystopian sci-fi. Gilliam has always worked at his own pace, and being a controlling and demanding perfectionist means that he has not churned movies out regularly, and that each film that he makes is a passion project. As a director, Gilliam is notorious for going over-schedule and over-budget, and for having some disastrous productions, as well as a number of box office bombs.

But almost every Gilliam film bursts with creativity and originality, and is risky, visually rich, and exciting. Sure, his movies are often messy and chaotic, but they’re rarely dull. Terry Gilliam’s films are to be cherished for their practical sets, props, and effects — there is a high chance we will not see their like again.

13. Tideland

Jodelle Ferland Doll Head on Finger in Tideland

"Tideland" is the story of a nine-year-old girl, Jeliza-Rose (Jodelle Ferland), whose drug-addicted parents (played by Jennifer Tilly and Jeff Bridges) die, resulting in her living alone in a rural shack. She befriends two strange neighbors — Dell (Janet McTeer), and her childlike son Dickens (Brendan Fletcher) — and copes by creating a fantasy world.

It is perhaps no coincidence that Gilliam’s two worst films were both released in 2005, while he was preoccupied attempts to make "The Man Who Killed Don Quixote" with Johnny Depp. The issues with "Tideland" are too complex to go into here, but let’s just say that dealing with real-world problems like drug and child abuse are not Gilliam’s forte. Attempting to combine these serious subjects with the kind of fantastical landscapes that he is known for does not work. Jodelle Ferland is extraordinary, even if the experience of watching what she goes through is deeply uncomfortable to watch.

12. The Brothers Grimm

Heath Ledger and Matt Damon in The Brothers Grimm

"The Brothers Grimm" saw Gilliam return to the kind of high fantasy he is best known for, recalling the likes of "Time Bandits" and "Baron Munchausen." The Grimm brothers are charlatans who extort money from villages against the backdrop of French-occupied Germany in the 18th century. They are then dispatched to take on a real haunted forest, with the help of Angelika (Lena Headey).

Unfortunately, one of the main issues here is the hugely miscast Matt Damon as one half of the titular brothers, with the much better-suited Heath Ledger as the other. In addition, the plot is confusing, the film is messy, and it’s hard to care about anything that happens. The best aspect — Monica Bellucci as the wicked Mirror Queen, adorned in fabulous costumes — does not appear nearly enough. "The Brothers Grimm" doesn’t have the scope or scale of Gilliam’s best fantasy work, it’s confined to one forest for too much of its runtime, and although there are a couple of interesting creatures who appear towards the end, we have checked out by the time they arrive.

11. Jabberwocky

Michael Palin in Jabberwocky wearing chainmail

A Terry Gilliam adaptation of Lewis Carroll’s famously weird and wonderful poem starring Michael Palin sounds like the ingredients for a good time. However, apart from a brief bit of narration at the beginning and the appearance of the "monster" at the end, "Jabberwocky" has very little to do with Carroll’s work. Very much a continuation of the style established in "Monty Python and the Holy Grail" and "Life of Brian," but without the whole Python ensemble and, crucially, the writing team behind them, "Jabberwocky" ends up being quite dull.

As a huge Michael Palin fan, it pains me to say this, but he can only work with what he’s given. Naming the film "Jabberwocky" sets up certain expectations — you will spend the entire runtime waiting for them to filled, but by the time the creature finally appears, it’s too little, too late. Palin plays a typically naïve and optimistic character who struggles to survive in a hostile medieval world, but it’s all very grim and not quite funny enough.

10. Fear and Loathing in Las Vegas

Benicio Del Toro, Johnny Depp in Fear and Loathing in La Vegas driving stoned

I will admit to being very into "Fear and Loathing in Las Vegas" (both the book and film) during my college years, but upon re-watch, the movie doesn’t exactly hold up. In a feature-length drug trip that could serve as a cautionary tale, Benicio Del Toro and Johnny Depp both brilliantly convey the relentless paranoia, mania, and physical side effects that comes with a suitcase full of narcotics. This is definitely an outlier on Gilliam’s filmography — it feels more like a direct line into the mind of Hunter S. Thompson, and less the product of Gilliam’s imagination.

However, some of the drugged out visual effects are Gilliam-esque, such as the carpet melting up someone’s legs and the faces that stretch as they ominously lean towards our two "heroes." Christina Ricci and Ellen Barkin both cameo in uncomfortable scenes that reveal Gonzo’s (Del Toro) misogyny. The scene in which the duo attend a DA convention does hold up, and an almost unrecognizable Tobey Maguire as a nervous hitchhiker is another highlight. Ultimately, this is a valiant attempt to adapt an unfilmable book, which is perhaps what gave Gilliam the hubris to think he could take on "Don Quixote."

9. The Zero Theorem

Christoph Waltz in The Zero Theorem pads on head

Like "Brazil" and "12 Monkeys" before it, "The Zero Theorem" is at the dystopian end of Gilliam’s fantasies, forming the third part of the director’s "Orwellian triptych" (although, really, these films feel more influenced by J. G. Ballard). Set in a bureaucratic nightmare, "The Zero Theorem" stars Christoph Waltz as Qohen, a depressed computer programmer who refers to himself as "we." There are several stars in small supporting roles, including as Matt Damon as Management, Tilda Swinton as an AI therapist, and Ben Whishaw as a doctor. David Thewlis plays Qohen’s boss, and Lucas Hedges plays Management’s teenage son Bob, who is assigned to help him.

The title of "The Zero Theorem" refers to Qohen’s work — he tries to prove a mathematical formula that shows that life, the universe, and everything will end in a meaningless void. Despite slipping under the radar and receiving middling-to-negative reviews, "The Zero Theorem" holds up with some of the best and most inventively creative of Gilliam’s work, offering the same absurd comedy and exceedingly bleak outlook as "Brazil."

8. The Adventures of Baron Munchausen

John Neville in The Adventures of Baron Munchausen

"The Adventures of Baron Munchausen" is probably the movie I would tell someone to watch if they’d never seen a Gilliam film and wanted to get a sense of who he is as a director. It’s a fantasy epic stuffed to the gills with the gorgeously intricate practical props and sets that define Gilliam’s aesthetic. It stars John Neville, an actor who had not appeared in a film for 18 years, as the Baron, and future director Sarah Polley as little Sally Salt, a stowaway on the Baron’s adventures.

Said adventures include a trip to the moon, where the heroes encounter the head of the Moon King (Robin Williams) and a former ally of the Baron’s, Berthold (Eric Idle), a supernaturally fast runner. Oliver Reed and Uma Thurman have very small supporting roles, although Thurman’s Venus making her entrance in a giant clamshell is one of the film’s more memorable images. Like almost all of Gilliam’s work, "The Adventures of Baron Munchausen" is funny, completely chaotic, and full of visual wonder.

7. 12 Monkeys

Bruce Willis, Brad Pitt in 12 Monkeys

"12 Monkeys" may make for uncomfortable viewing at the moment, as it is set in the near-future, where almost the entire population of the planet has been wiped out by a virus. James Cole (Bruce Willis) is sent back in time, but accidentally ends up in 1990 and is placed in a psychiatric institution (which appears to be from 1890) due to no one believing he is from the future. There, he meets Jeffrey Goines (an Oscar-nominated Brad Pitt) and Dr. Kathryn Railly (Madeleine Stowe), who will both prove important later on.

The futuristic scenes, in which Cole is strapped to a chair and a team of scientists probe him for information, are the best and most typically Gilliam-esque sections. Although this was Gilliam’s biggest box office hit and his most widely-seen film, it’s not the movie that’s most indicative of his style. It features the usual time travel tropes, such as paradoxes and the butterfly effect. Between this and 1997’s "The Fifth Element," Bruce Willis starred in two of the best sci-fi films of the ’90s.

6. The Imaginarium of Doctor Parnassus

Heath Ledger in The Imaginarium of Doctor Parnassus

While still reeling from his many futile attempts to get "Don Quixote" off the ground, Gilliam started another project that would also face a huge challenge during production: the tragic death of its star, Heath Ledger. This led to a uniquely creative solution. Ledger was replaced with three other actors — Johnny Depp, Jude Law, and Colin Farrell. It’s a move that works surprisingly well, and one that only Gilliam could get away with.

"The Imaginarium of Doctor Parnassus" also stars Andrew Garfield, Lily Cole, Verne Troyer, and Christopher Plummer as Doctor Parnassus himself, who form a travelling troupe of players who lure audience members through a magic mirror into the "imaginarium." Garfield in particular is brilliant as Anton, who becomes jealous of Ledger’s Tony, a man with amnesia who the performers find dangling under a bridge.

When Tony transforms into the other actors in the imaginarium, it all forms a seamless part of the weird and wonderful world that Gilliam creates. Juxtaposing the present day setting with fantasy elements worked well in "The Fisher King," and is successful here, too. Gilliam’s productions are notoriously chaotic, but in this case a triumph was pulled from the jaws of tragedy.

5. Time Bandits

Time Bandits dwarves drink from cups

"Time Bandits" joins "Labyrinth," "Willow," and "The NeverEnding Story" in the pantheon of great family-friendly fantasy films from the ’80s. It concerns a band of dwarves, including Fidgit (Kenny Baker), who have a map that identifies holes in the fabric of space-time that they use to steal treasures from different points in history. An 11-year-old boy, Kevin, gets inadvertently swept along on their adventures, plucked from his mundane suburban life and whisked away from his parents, who are obsessed with consumerism (those Ballard influences again).

While traveling through time, the thieves try to keep a step ahead of Evil (David Warner); some highlights on their trip include John Cleese as Robin Hood, Sean Connery as Agamemnon, and (especially) Ian Holm as Napoleon. The most memorable sequences are the one in which Kevin and the bandits are on a ship that is revealed to be a giant’s hat, and the one in which they are they held in a cage above a bottomless pit. "Time Bandits" includes some surprisingly sharp satire, while also being a rollicking ride for kids (allegedly, there’s a TV adaptation coming from Apple and Taika Waititi, too).

4. The Fisher King

Mercedes Ruehl lounges on couch Fisher King

"The Fisher King" is a very different take on the Grail myth from Gilliam, away from his fellow Pythons. It stars Jeff Bridges as Jack, a shock jock based on Howard Stern who meets Robin Williams’ kind-hearted homeless man, Parry, while at a low-point in his professional and personal life. After discovering that they are connected, Jack vows to help Parry, which includes giving him the courage to track down and talk to the woman who he believes he loves.

A highlight of the film is Mercedes Ruehl as Jack’s long-suffering girlfriend Anne, in an Oscar-winning performance. Parry is obsessed with finding the Grail, which he believes resides in the home of a New York millionaire, and is tormented by visions of a Red Knight — both of these are manifestations of the trauma he experienced while witnessing his wife’s murder. Williams and Bridges play off one another beautifully, and once again Gilliam successfully combines a modern-day setting (which has smatterings of a classic New York rom-com) with the fantasy elements that we know him for.

3. Monty Python and the Holy Grail

Monty Python and the Holy Grail knights on a quest

"Monty Python and the Holy Grail" was the first Python film to have a plot, instead of just being a connected series of skits. It was the directorial debut of the Python’s two Terrys — Jones and Gilliam — and proved to be a big learning experience for both of them. It is, of course, the writing that proves most memorable, making "Monty Python and the Holy Grail" one of the most-quoted comedies of all time. Between the Knights who say Ni, the Black Knight who refuses to die, the insulting Frenchmen, the murderous bunny, the witch, and Dennis, poor King Arthur’s quest for the Grail is not an easy one.

As in "The Life of Brian," Graham Chapman gives a charming central performance as someone put-upon by a variety of eccentric and hostile obstacles. Gilliam plays Arthur’s loyal servant Patsy, who gallops behind Arthur banging coconuts together. He also appears during the animated cave sequence — the threat is quashed because the animator (Gilliam) suffers a fatal heart attack, meaning the "cartoon peril was no more." Many of the elements that recur in Gilliam’s films first appeared here.

2. The Man Who Killed Don Quixote

Adam Driver, Jonathan Pryce in The Man Who Killed Don Quixote

There aren’t many films that have had such a tumultuous gestation period that they have had no less than two documentaries made about them, but "The Man Who Killed Don Quixote" is no ordinary movie. Production began in 2000, with Johnny Depp and Jean Rochefort in the lead roles, but on-set problems scuttled the project after just a few days of shooting. In the intervening years, a number of actors were attached to the film, including Ewan McGregor, John Hurt, and Michael Palin, but it wasn’t until 2018 that this millstone around Gilliam’s neck finally made it to completion with Adam Driver and Jonathan Pryce (the star of "Brazil") as the stars. To get the full experience, the documentaries "Lost in La Mancha" and "He Dreams of Giants" are essential companions.

So, after two decades, could the finished result possibly live up to the behind-the-scenes drama? The answer is actually yes! The layers involved here are mind-meltingly complex — a film within a film, telling a story in which a man creates his own myth about himself — but it still has all of Gilliam’s surreal comedy and fantastical touches, including giants. Both Driver and Pryce are brilliantly tuned-in to Gilliam’s tone, with Driver bringing hilarious physicality to his role. The only frustration is that nobody saw it. I strongly urge you to rectify that.

1. Brazil

Jonathan Pryce in Brazil strapped in chair baby mask

There can be no denying that "Brazil" is Terry Gilliam’s masterpiece. Its influence can be felt in the Ministry in "Harry Potter," the Commission in "The Umbrella Academy" and the TVA in "Loki." A dystopia that is heavy on analogue bureaucracy, in which ducts, pipes, and tubes rule over a world of blandly gray class of middle managers, pen pushers, and civil servants, "Brazil" creates a terrifying world out of the banal and mundane.

With Robert De Niro as a revolutionary hero, Michael Palin playing against type as a chilling villain, and Jim Broadbent as a plastic surgeon who gets truly transformative results, the supporting cast revolves around an extraordinary central performance from Jonathan Pryce as Sam Lowry. The set and costume design, like in most Gilliam projects, is where the richness of the world is created — Lowry is an Icarus figure in his dreams, there’s a restaurant that serves green dinner-flavored mush, and a horribly scary finale takes place in a cavernous torture chamber. The details in this movie will be unpacked for decades to come; "Brazil" will only become more relevant with age. A breathtaking achievement — and one of the best Christmas movies!