The Essentials: The Best Films Of Terry Gilliam Ranked

Terry Gilliam is a visionary —no, Terry Gilliam is a has-been. Terry Gilliam is a grouch… but wait, Terry Gilliam is a delight. Terry Gilliam is a Python. But hang on, didn’t he “just” draw the pictures? There’s almost no declarative statement you can make about Terry Gilliam without someone offering a direct contradiction, and without that contradiction containing at least the seeds of some truth. So let’s start with something easier: Terry Gilliam is an American director who … except he’s not, he’s British.

Bugger it.

The facts are these. A 73 year-old American-born director, screenwriter, actor, animator and founding member of the Monty Python comedy troupe, Terry Gilliam has had one of the most fascinating on- and off-screen careers of recent years, and can inspire equal parts antipathy and adulation, often in the very same individual and often at the very same moment. A political science major who became an advertising cartoonist, illustrator and animator after college, by his own account he defected from America because he was worried he’d become a “full-time, bomb-throwing terrorist” in response to what he saw as the rising tide of authoritarianism in the U.S., especially with respect to police brutality.

Naturalizing to British citizenship in 1968, Gilliam first met John Cleese, and then the other members of what would become Monty Python, and graduated from duties as the troupe’s animator and illustrator for LPs and book covers to full membership with co-writing credits on all of their works (and certainly you can see the sensibility of his early solo animations having a direct effect on the troupe’s live action TV shows and movies). The astoundingly influential Pythons gradually dissolved during the early 80s (though recently reformed for a run of stage shows), but Gilliam’s solo directorial career was already in its fledgling stages with 1977’s “Jabberwocky” and 1981’s “Time Bandits” taking place outside the Monty Python banner.

Since then he has attained dizzying heights and bends-inducing lows in terms of the quality of his output. His career always had its ups and downs, but latterly has seen more downs, as Gilliam’s hireability took a knock following some box-office disappointments and a string of high-profile setbacks, notably around the mounting of his Don Quixote movie. And it’s probably fair to say that as a filmmaker whose extensive imaginative reach will often exceed his grasp, perhaps the worst impediment to hit Gilliam’s career recently has been the availability of cheap CG, which makes it seem possible to deliver the kind of fantastical productions he wants to make within budget constraints. Possible yes, but advisable maybe not so much, as the plasticky, unconvincing CG that has marred some of his recent efforts is a million miles from the charming, inventive, in-camera visual style with which he made his name.

But whatever mix of conflicting emotions we feel toward Gilliam’s output at any one moment, he remains a character (and a terrific interviewee) who fascinates us, not least for the tumultuous nature of his career, and the endearingly outspoken way that he assesses it. With the release of his latest film “The Zero Theorem” (original review here), we thought we’d take a look back at Gilliam’s directorial career in full, so here’s our take on each of his films, ranked from worst to best.

One title that does not appear, as he did not direct it, is the very great documentary “Lost In La Mancha,” but it’s a vital watch for anyone with even a passing interest in the craft of moviemaking, or in Gilliam himself. The doc, perhaps more than any of his own films, captures brilliantly what we love so much about Gilliam (even when we hate him) —endlessly tilting at the windmills of his imagination, deaf to the doubts of those around him, with a stubbornness so profound it becomes noble, he is cinema’s own Don Quixote.

17. “The Wholly Family” (2011, short)
Well, if you’re going to hit a nadir, better to do it with a 20-minute short film financed by a pasta company that few are ever going to see on the big screen —this was rejected from at least one film festival on the grounds of being “an advertisement.” In fact, having an overtly commercial agenda is not a problem here: there are occasional platefuls of spaghetti featured, but they’re no more shoehorned in than any other element of this trite, badly acted and frankly ugly little film. Along with “The Legend Of Hallowdega,” a product of one of Gilliam’s wilderness periods in which he was happy to take commercial sponsorship for short projects provided the sponsors more or less left him alone, “The Wholly Family” was financed by pasta brand Garofolo who mandated it be shot in Naples, but other than that it’s all Gilliam. And it is unmistakably Gilliam, though at his worst: a thin, rather obvious fairytale that amounts to very little except a series of grotesque dreamscape scenarios in which a little boy learns not to be bad. Based around a Pulcinella figurine (a masked Neapolitan puppet related to the “Punch” of English “Punch and Judy” shows) who comes to life, even its modest scope seems to overstretch the budget —the miniaturization effect is almost as unconvincing as the title’s labored pun, and the mostly non-professional cast deliver self conscious and uncomfortable performances. Worst of all, there’s nothing of the gleeful anarchy of Gilliam’s early shorts here, just muddy, off-putting visuals in service of a strangely conservative agenda, wrapped up in a silly dream-within-a-dream structure.

16. “The Legend of Hallowdega” (2010, short)
The first of Gilliam’s two brand-sponsored shorts which came in between his features ‘Parnassus’ and “The Zero Theorem,” ‘Hallowdega’ is marginally more successful than “The Wholly Family” if only due to a slicker presentation. However, it suffers from the same issue that a lot of latter day Gilliam projects labor under: why was it made? What is its reason for existing? There’s nothing particularly urgent about its story —a load of hokum about the Talladega Superspeedway and how the racetrack was built on an Indian burial ground which accounts for all sorts of mysterious goings-on— and if the advertiser’s brand (AMP Energy Juice) is laudably absent from the film overall, it leaves a hole where the point of this whole endeavor should be. Of all things in the universe, why is Gilliam making a faux-documentary investigating manufactured crackpot theories about Talladega? There are occasional flashes of the old Python wit, such as the opening credits of a fake supernatural investigation show presented by Justin Kirk listing other wonders that he has apparently debunked, such as “The Pyramids,” “Atlantis” and “The Midwest,” and there’s nicely characterful casting of the “interviewees” and some nice inside-baseball cameos, but the central thrust, which concerns a crackpot conspiracy theorist played by David Arquette is just plain silly, and the film overall never displays the sort of teeth it would need to work as even a mild satire —on reality TV, on ghost myths, on racecar culture and its adherents—on anything, really. An uncomfortable-at-best marriage of Gilliam’s fascination with fantasy with a world that doesn’t organically suit such an approach, it’s one for completists only, and probably not even for them.

15. “Tideland” (2005)
Made as a sort of palate-cleanser after the tumultuous production and endless delays on “The Brothers Grimm,” which it ended up premiering almost simultaneously with, “Tideland” was much closer to unfiltered Gilliam than the former. Unfortunately, that didn’t turn out to be for the better. An adaptation of Mitch Cullin‘s coming-of-age novel, the film follows Texan girl Jeliza-Rose (Jodelle Ferland), who’s left to fend for herself after the death of her obese mother (Jennifer Tilly) and heroin-addict father (Jeff Bridges), with the usual cast of eccentrics (most notably Janet McTeer) popping up along the way. Southern gothic might be an interesting genre for Gilliam, but one for which he’s ultimately unsuited on this evidence, as the film feels like pastiche rather than something more deeply felt and authentic. It doesn’t help that the director’s stylistic tics are dialed up all the way, to the extent that you worry that the dutch angles are down to a wonky tripod that no one could afford to replace, rather than any kind of actual choice. And though the cast, particularly Ferland (who should have gone on to bigger things) are fine, most are wasted. If anyone was sold on the idea of a reunion between Gilliam and Bridges, they’ll be disappeared to learn that “The Fisher King” star is a corpse rotting in a chair for 80% of the running time. It’s misjudged on a number of levels, but most important of all is the tone. Arguably the darkest of all the director’s movies, the film comes across as an unpleasant wallow, a Lars Von Trier-style piling-on on a young girl, particularly in the thoroughly icky scenes between Ferland and Brendan Fletcher‘s local man-child. Perhaps there was initially meant to be a point, but in finished form, none is apparent.

14.“The Imaginarium of Dr Parnassus” (2009)
There are films that can recover from disaster-beset shoots, films that emerge as a triumph of creative vision and teamwork over adversity, films that stand as testament to the powers of persistence over the forces of dumb luck and unforeseeable tragedy. But as much as we all hoped all of the preceding would be true, ‘Parnassus’ was not one of those films, with the finished product wearing all the troubles of its conception on its sleeve and then some, feeling stunted, hurried, and shoddy when it finally stumbled onto screens. The most dramatic of those issues was of course the untimely death of the film’s star, Heath Ledger, who had filmed roughly a third of his scenes when he died, forcing a major retooling of the production. However the solution as such was actually pretty inspired. As Ledger’s role required him to change as he progresses through various dream states, Gilliam elected to recast the role three time over, so that ultimately Ledger, Johnny Depp, Jude Law and Colin Farrell all portrayed the same character at different times. The increase in star wattage alone seemed to suggest this might in fact enhance the film. And indeed, none of the stars are to blame for the film’s failures, and the readiness with which they stepped up remains a touching tribute to their departed friend. For better or worse, Gilliam is the author of his films, and here the incomprehensible storytelling (he co-wrote the script with Charles McKeown) and the flat-lit cheap CG aesthetic that is employed as soon as the film proceeds into the characters’ imaginations (ie pretty much all of the time) and which hardly looks like something released the same year as “Avatar,” speaks for itself. It’s a real shame, as the non-CG practical sets used early on are quite lovely, and the cast is rich in character from the central quartet to the supporting roles filled by Christopher Plummer, Andrew Garfield, Lily Cole and Tom Waits, perfectly cast as the Devil. But no amount of window dressing can distract from the convoluted, stakes-free narrative that ‘Parnassus’ delivers —less the wild, wondrous journey into the imagination that it should be, and more a tiresome parade of disconnected, half-baked vignettes that taken together amount to a great deal less than the sum of their parts.