8. Jabberwocky (1977)
In a classic but unglamorous hero’s journey, an ordinary peasant (Michael Palin) is accidentally entrusted with ridding his homeland from of a terrible monster so frightening it turns any witness’s teeth white.
Perhaps inevitably, given Michael Palin’s prominence in the lead role and the film’s placement between Python movies, Jabberwocky feels the most similar of Gilliam’s solo efforts to the surrealist comedy troupe’s work.
Jabberwocky gives us a grim, absurdist farce set in an appropriately muddy, bloody and scatological facsimile of Medieval England ruled over by King Bruno the Questionable (Max Wall, so memorably barking “kill that man!” and wiping viscera from his face as he watches a jousting tournament) and plagued by a legendary beast they could (perhaps mercifully) only afford to actually show once. It’s economical, but pretty funny and effective as these things go.
7. Monty Python and the Holy Grail (1975)
King Arthur (Graham Chapman) and his Knights of the Round Table are given a quest by God and undertake a search for the Holy Grail.
Monty Python and the Holy Grail was co-directed with Terry Jones and therefore reflects a mixed creative vision so it would be unfair to put this any higher than midway through this list, but it’s impossible to not acknowledge this always-hilarious work in any discussion of Terry Gilliam’s career.
There was a perhaps apocryphal adage at the time that Terry Jones was good at corralling the actors but Terry G was the one who made it all “look like a real movie”. However, the artistic labour was divvied up, and the Pythons ended up making one of the most iconic, endlessly quotable, and very silly British comedies of all time. Essentially a series of loosely connected Arthurian sketches with a self-aware, budget-saving master stroke of a finale, every lover of surrealist antics remembers the Witch-Weighing, the Bridge of Death, the Killer Rabbit and of course the Black Knight for a reason: the Pythons really were the best there was.
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6. Fear and Loathing in Las Vegas (1998)
A journalist (Johnny Depp) and a lawyer (Benicio Del Toro) go on a road trip to Vegas and proceed to lose their minds on a variety of psychoactive substances.
To properly adapt Hunter S Thompson’s anarchic and transcendental work, you probably have to be a little bit mad yourself. And, for a project that looked a little like director-for-hire work for a studio at first, this ended up being one of Terry Gilliam’s most vividly memorable films.
Fear and Loathing has Johnny Depp and Benicio Del Toro both on fine form in a madcap psychedelic road trip that, along with Requiem for a Dream stands as one of the best ecstasy to agony drug movies. Don’t try to understand everything, just go with the addled dream/nightmare logic and enjoy the bewildering sensation.