The Essentials: The Best Films Of Terry Gilliam Ranked

6. “Fear And Loathing In Las Vegas” (1998)
Terry Gilliam‘s version of “Fear And Loathing In Las Vegas” was almost not made at all —”Repo Man” helmer Alex Cox had been developing Hunter S. Thompson‘s gonzo classic (after the likes of Ralph Bakshi, Martin Scorsese and others failed to get it over the line), but fell out with producers only a few months before it was due to go before cameras, with stars Johnny Depp and Benicio Del Toro already in place. Gilliam was brought in, wrote a new script with Tony Grisoni in ten days, and within a year, the film was premiering at the Cannes Film Festival. It’s an appropriate origin story for a film of Thompsons’ manic, drug-fuelled memoir of a long weekend in Vegas with his attorney, and one that explains why, for all the film’s inventiveness and faithfulness to the original source material, it’s not successful. But given that the book was considered unfilmable for many, it’s a damn good effort, and it’s hard to imagine anyone but Gilliam coming close. It helps that his cast are so game. Depp (a close friend of Thompson) has rarely been better, Del Toro is his perfect foil, and cameos including Tobey Maguire, Ellen Barkin and Christina Ricci are all satisfying. Gilliam’s trademark techniques are starting to reach a kind of fever pitch, but it works here because of the heightened, nightmarish, drug-addled tone, and he captures Americana here in a way that “Tideland” doesn’t come close to, perhaps because he’s most interested in Thompson’s story as a sort of farewell to the 1960s. The director and the author are clearly kindred spirits, and no attempt to film his work before or since has felt so close to getting the essence of the writer, even if it means that the film creeps towards tedium in places. That said, for the most part, it’s funny, a little melancholic, and occasionally even dazzling.

5. “Twelve Monkeys” (1995)

Famously based on the utterly brilliant Chris Marker photomontage film “La Jetee,” perhaps “Twelve Monkeys” was always going to seem a little like a bloated version of that film’s lean, evocative storytelling to anyone who has seen both. But if we’re going to go bloated, then this is a terrifically fun way to do it, with even more unnecessary additions, like the subplot about the titular shady organisation, yielding some enjoyable elements, such as Brad Pitt’s memorably manic, twitchy performance. Mostly, though this is a clever exercise in expanding an airtight sci-fi premise into a brainier-than-usual blockbuster, with room for two major Hollywood stars to play against type —hunky Pitt as the squinty mental patient and action megastar Bruce Willis as the confused, usually frightened time traveler who can only negotiate his fraying mental state with the help of Madeleine Stowe’s doctor. There are the very “Brazil”-esque future sequences, and the mental institution is similar to that featured briefly in “The Fisher King,” so Gilliam is well within his wheelhouse. But “Twelve Monkeys” really shows what he could do when working off a cleverly constructed script (David and Janet Peoples did the adaptation), and with such compelling structure to anchor Gilliam’s more fanciful tendencies, the film manages to dazzle but also to impress emotionally and logically. So it’s an exciting adventure, a thought-provoking science fiction yarn, a surprisingly effective love story and a post-apocalyptic tragedy all at the same time. Most impressively, even for those of us expecting the magnificent twist ending preserved from “La Jetee,” the film still manages to make that element work all over again, giving us that same wonderfully doomy sense of the unbreakable cycle of destiny.

4. “Time Bandits” (1981)
The film that made Gilliam’s name as a solo filmmaker, and still probably his most unqualified commercial success (it was the tenth top-grossing movie of 1981, grossing $42 million), “Time Bandits” might also be Gilliam’s most purely enjoyable fantasy. As you might imagine for a script co-written with Michael Palin, the story —which involves an eleven-year old boy, Kevin (Craig Warnock) accompanying six dwarves (David Rappaport, Kenny Baker, Malcolm Dixon, Mike Edmonds, Jack Purvis and Tiny Ross) on a time-hopping quest for treasure in which they are pursued by the personification of Evil (David Warner, in one of the all-time great turns of comic villainy)— has a decidedly Pythonesque sense of humor. That’s not least in the excellent selection of starry cameos, including John Cleese as Robin Hood, Ian Holm as Napoleon and Sean Connery as Agamemnon. But unlike “Jabberwocky,” the Python influence isn’t overwhelming here. Gilliam has found his own voice as a filmmaker, and it’s capable of scaring you, exciting you, awing you, and even making you choke up a little bit. For all of the script’s cleverness, Gilliam keeps it just this side of arch, with a real story to tell, distinctive fantasy worlds, and a sense of classic children’s literature throughout, not least in that hilariously bleak Hilaire Belloc-ish conclusion. It’s almost impossible to imagine these days that a film as idiosyncratic, strange and brilliant as “Time Bandits” could have been a blockbuster hit. Let’s just hope we see more like this from Gilliam again at some point.