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The Essentials: The Best Films Of Terry Gilliam Ranked

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3. “Monty Python and the Holy Grail” (1975)
So where does the genius of Monty Python end and where does the genius that is Gilliam at his best begin? It’s appropriately difficult, given the anarchic and inexplicable nature of the troupe, to tell how much they fed into/fed off one another, so let’s not even bother trying. Suffice it to say that co-director Terry Jones is largely credited here with directing the actors while Gilliam was in charge of the photography and of course the animation. His tendency to take smaller acting roles within the troupe’s output can mistakenly give the impression that he was somewhat peripheral, yet Gilliam, the sole American in a very British bunch, was entirely a Python, and his animation style provided the Pythons with their most recognizable iconography. Those unmistakable photo collage-style jerky animations set against Victorian/Baroque backdrops that can at any moment be summarily squashed by a giant foot or puked up by a giant beanstalk/vine. And in ‘Holy Grail,’ an unassailable comedy touchpoint that regularly tops comedy polls, Gilliam’s animations often take center stage, not just as interstitial moments but as self-contained chapters, and, most memorably, when Gilliam appears onscreen as the animator dying of a heart attack halfway through drawing the Legendary Black Beast of Arrgh! thereby allowing the Arthurian knights to escape its ravenous clutches. One of the elements that made Monty Python so irresistible was this meta-fuckery, messing with form as well as content to truly bizarre and eternally surprising effect, and the outsider perspective that Gilliam brought as both an animator and an American is a vital component. This is silliness raised to the level of an art form.

FIsher King

2. “The Fisher King” (1991)
Brazil” may be Gilliam’s undisputed masterpiece, but if there is such thing as a disputed masterpiece in his catalogue, it may just be “The Fisher King,” which has never, perhaps until recently, received the adulation we’d say it deserves. This isn’t just revisionism in the wake of Robin Williams’ death, as the film has been one of our favorite Gilliam works ever since it was made. It’s remarkable for expertly walking the line between sentiment and horror, so that all its colors of light and darkness have meaning, and all are supremely well-earned. But of course it is hard to think of the film now without added melancholy resonance. Williams’ performance here was always terrific: the character of Parry allowed him off the leash at times (all dutch angles, manic renditions of “I Like New York In June,” and stories about little fat fairies), but it also let him embody a real man who had suffered unthinkable trauma and whose mind had transmuted that terror into literal dragons and demons. Playing off a similarly mid-career-high role from Jeff Bridges (along with “Fearless” perhaps his most underrated turn), Williams owns this role —it’s impossible to imagine anyone else who could have sold its dizzying turns from joy to despair to mischief to abject fear, and as an analogy for depression (here trauma-induced, but a mental disease nonetheless) it’s now almost unbearably prescient. Parry’s lovable, generous, clownish persona masks darkness and pain within, and the devils he suppresses can return to do battle with him without warning. As a film it’s anything but serious, yet its shining humanism reaches almost philosophical levels, and while we’ve always held the Grand Central waltz moment to be one of the most transcendent in the history of filmmaking, recently we’ve come to consider Parry’s soliloquy where he tells the story of the titular King in a similar light; “I only knew that you were thirsty.” Here Gilliam’s bizarro folkloric vision (featuring wonderful turns too from its supporting females Amanda Plummer and the Oscar-winning Mercedes Ruehl) is cut with real-world implications and emotions, leading to one of his most satisfying films, and one that has now and forever been lent an extra layer of heart-slicing poignancy for earning the happy ending for Robin Williams’ Parry that the actor was denied in life. See it and be nicer to everyone as a result.

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1. “Brazil” (1985)
Still the most complete, influential and perfectly realized of all of his features, and the high watermark that his fans are most likely thinking of when they wish he’d make movies like he used to, “Brazil” is Gilliam’s masterpiece. A dystopian fantasy of such heartfelt despair and peculiar beauty —but always undercut by that impish Python humor— it’s in “Brazil” that Gilliam most convincingly married his animator’s eye for set design, photography, and even costuming with his political philosophy and personal storytelling sensibilities. Elements of “Brazil,” such as his very droll eye for the absurdities of petty bureaucracy, were foreshadowed in previous works; other elements would recur often thereafter, such as the thin line between imagination and insanity that is arguably the characterizing concern of every subsequent Gilliam movie. But while he’d return to this theme time and again, he’d never subsequently attain quite such thrilling and persuasive heights, nor achieve such a dense, textured sense of a lived-in world. Gilliam can always be relied upon for oddball side details and characters, and here those abound, from Robert De Niro’s molelike terrorist/air conditioning repairman (De Niro was so high on this script he agreed to take this smaller role despite being originally interested in the larger Michael Palin part), to Jim Broadbent’s plastic surgeon, but the film is anchored by a terrifically sympathetic and underplayed everyman turn from the perenially undervalued Jonathan Pryce, who somehow allows us to constantly access the humanity underneath all the immensely enjoyable tricksiness. And it simply has one of the most compelling storylines of any Gilliam film —it’s a dark, Orwellian cautionary tale about the dangers of complacency and unquestioning submission to authority. Gilliam’s work with Monty Python feels like little proto-anarchist tracts and essays, a naughty schoolboy taking pot shots at the headmaster with his slingshot. But “Brazil” is his manifesto, and here he has graduated from catapult to cannonade —it’s a fantastically angry, funny, deliriously imaginative film, a flight of fancy that somehow delivers a real gut punch.

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Energetic polymath that he is, Gilliam has been involved with many other projects over the years —stage shows, television commercials, the recent Python stage show reunion, collaborations with bands like Arcade Fire and Gorillaz, and even opera. And as an actor he pops up pretty frequently too —we’ll next see him in a tip-of-the-hat cameo performance in the Wachowskis’ “Jupiter Ascending.” And the list of films he nearly made or was attached to at one time or another is long and storied: he was famously JK Rowling’s first choice to direct ‘Harry Potter’; his adaptation of Neil Gaiman and Terry Pratchett’s comic apocalypse novel “Good Omens” flares to life every few years; same goes for “The Defective Detective,” a script co-written with “Fisher King” collaborator Richard LaGravenese; not to mention a screenplay ready to go called “Mr. Vertigo” that was co-authored by Paul Auster.

But his longest-running on-again off-again saga, one seeming such a perfect encapsulation of the brilliant, maddening, magnificent folly that is Gilliam’s filmmaking career is of course “The Man Who Killed Don Quixote” which is, and I can’t believe we’re actually reporting this again, apparently back on track now for the zillionth time. We really, really hope it comes together for Gilliam this time, because of all his unmade projects, we can’t imagine one better suited to his peculiar, eccentric talent. At his best there is no one more wondrous, at his worst no one more disappointing. But at either extreme and all points in between, Terry Gilliam is utterly unique; a precious resource for whom we couldn’t be more thankful. — Jessica Kiang with Oliver Lyttelton

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