Every Terry Gilliam Movie Ranked Worst To Best

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.

"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.

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."

"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.

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.

"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.

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.