What to make of director Terry Gilliam, the director behind films like Monty Python and the Holy Grail, Brazil, The Fisher King, 12 Monkeys *and the just-released *Zero Theorem? He is a singular visual stylist — and beloved by actors who’ve worked with him, like Johnny Depp, Sean Connery and Jeff Bridges — who chases his own muses into obscurity and disaster? Was there ever a chance for him, or was he destined to simply be the Least Likely to Succeed?

Everyone loves an underdog.

Johnny Depp, Matt Damon, Heath Ledger, Robert De Niro, and Sean Connery gave him their stamp of approval. Geek auteur Zack Snyder calls him “a genius.” J.K. Rowling dreamed he would be the one to first shepherd Harry Potter into cinematic existence. Director Bong Joon-ho paid him a not-so-subtle tribute in 2014’s critically acclaimed sci-fi film, Snowpiercer; John Hurt’s character name is “Gilliam.”

When handed the opportunity to jump from sketch comedy animator to full-fledged director, Terry Gilliam planted a flag on the fringes of the mainstream and never looked back. At once rebellious and classical, vicious and airy, imaginative yet ready to snap his audience back to harsh realities whenever he damn well pleases, Gilliam is a singular stylist who speaks the blockbuster language with a hallucinogenic cadence. Each of his films — including his latest, The Zero Theorem — feels like the pinnacle of his Gilliamness: oppressed commonfolk fighting “the man” in alternate universes filled with doohickies and creepy ideologies. And settled against Hollywood product, each film feels like a revelation. Idiosyncrasy means box office bombs outweigh the successes — yet he’s never really failed. Not at concertizing dreams, the director’s modus operandi. The movie business doesn’t have room for Terry Gilliam. Like the characters he’s wrangled in the last 40 years, that’s only made him fight harder.

Gilliam was born in Minneapolis, not England (despite going on to define humor for an entire generation of Brits). The political science major jumped the Atlantic in his 20s to work with Mad Magazine comic artist Harvey Kurtzman on his latest publication, Help!. Some might classify young Terry Gilliam as a hippie: long hair, trippy art, and a anti-establishment agenda. Explaining his relocation to Salman Rushdie in 2003, “I became terrified that I was going to be a full-time, bomb-throwing terrorist if I stayed [in the U.S.] because it was the beginning of really bad times in America.”

Initially, Gilliam joined Monty Python as a graphic comedian, lending his animation skills to Flying Circus’ sketch breaks. His work contextualized the troupe’s off-the-wall antics; Bubbly cartoons, Victorian era cutouts, erratic motion paired with sophisticated dialogue — audiences understood “Pythonesque” because of its deranged, illustrative shell. When Gilliam transitioned to live-action, he took his comic framing and the off-kilter behavior with him. Monty Python and the Holy Grail’s killer rabbits are the obvious extension, but even The Adventures of Baron Munchausen’s transplants actors into fantastical dioramas — like the layers of cel animation — while 12 Monkeys invading-your-personal-space close-ups mimic the talking heads of his early animated creations.

Gilliam’s affection for substantive absurdism made his promotion to full Python member natural. Terry Jones, Michael Palin, John Cleese, Eric Idle and Graham Chapman didn’t tell jokes, they roasted culture. Gilliam’s eye made the comedy transcendent. Holy Grail is every bit a sketch movie as Kentucky Fried Movie and Tunnel Vision, but Gilliam and Jones’ (they co-directed Python’s first big screen venture) give it the grit and gravity of an epic like El Cid. If it weren’t for clopping coconuts replacing the horses, King Arthur and his squire traversing the misty fields of England would look like a legitimate adaptation of Le Morte d'Arthur. Python’s comedy — and all of Gilliam’s films — tuck comedy inside familiar drama.

Once a Python, always a Python. After the comedy troupe dissolved in the ‘80s and Gilliam went off on his own, the animator-turned-auteur veered into magical realism where his dreamy, frantic, tomfool sensibilities prospered. Riffing on Lewis Carroll for 1977’s Jabberwocky was even more fitting than Arthurian lore; Alice doesn’t appear in the fantasy-skewing monster movie, but Gilliam’s career is full of characters falling down rabbit holes. The accidental hero of Jabberwocky; an 11-year-old fourth-dimensional traveler from Time Bandits; the lowly worker bee of Brazil’s dystopian bureaucracy, and more literally, the imaginative girl who distracts herself from a drug addict father through fantasy in 2005’s Tideland.



As Gilliam’s characters yearn for escape, the director has fled anything resembling convention. After Time Bandits’ success, the producers of 20th Century Fox’s Enemy Mine offered Gilliam the directing gig. He turned it down (the job went to Wolfgang Petersen) in favor of Brazil, a sci-fi film bottling up his long-standing fear of government and suppressive practicality. Brazil remains Gilliam’s masterwork, a biting outlook combined with iconic images (see: Jonathan Pryce soaring with angel wings) and Michael Kamen’s earworm score. It’s also the quintessential Gilliam behind-the-scenes disaster tale. Before releasing the film, Universal recut the director’s darker, preferred version. Gilliam fought producers over the release of his version, which eventually found its way to theaters in 1985 (yet another version that played European theaters ran an additional 10 minutes).

As studio priorities shifted, so did Gilliam’s standing with them. The Fisher King swapped alternate dimensions with bustling New York City, Robin Williams and Jeff Bridges channeling Gilliam’s heightened archetypes for an emotional tragedy. It earned Oscar love. It made sense. The mind-bending 12 Monkeys attracted Bruce Willis, hit theaters after the third Die Hard, and costarred up-and-comer Brad Pitt. It made sense. Production companies involved with Fear and Loathing in Las Vegas had worked tirelessly to get an adaptation of Hunter S. Thompson’s gonzo journalism novel off the ground. Gilliam and Johnny Depp gave it a bump. It made sense.

Between the successes were failed projects mucked up in budget and casting disputes. The world will never see Gilliam’s versions of Watchmen and A Tale of Two Cities, but they almost did. The one-two punch of The Man Who Killed Don Quixote and The Brothers Grimm sent Gilliam retreating to indie film, but it’s hard to imagine a filmmaker with manic energy, aggressive styling, and a resistance to beginning-middle-happy-ending plotting making it in the blockbuster-heavy studio system.

Don Quixote notoriously blew up in Gilliam’s face, after lead actor Jean Rochefort’s health took a turn, flooding, and insurance problems crippled the active production (for the full story, catch up with the 2002 making-of doc Lost in La Mancha). A rebound project, the Matt Damon/Heath Ledger fantasy Brothers Grimm pitted Gilliam against Bob and Harvey Weinstein, mega-producers who insisted on budget constraints, design changes, and final edits. Taking two years after production to finally get released, Gilliam found time to slip away and make Tideland.

Films like 2009’s The Imaginarium of Doctor Parnassus and this month’s Zero Theorem reflect a filmmaker unchanged by the evolving movie business. Disaster continues to strike Gilliam — Ledger passed away in the middle of shooting Doctor Parnassus, forcing the director to rewrite the script on the fly — but his approach acts as a lightning rod. His free-form, dream-to-screen adaptations feel more like the circus, indulging in imagery rather than establishing rhythm. He returns to a well time and time again; Zero Theorem updates the Brazil humans-as-cogs for the iPad addicted age, Christoph (“That’s a bingo!”) Waltz sparking as he downward spirals into hyper-florescent hell.

Gilliam’s as angry, mesmerized, gleeful as ever. It’s hard to call him an underdog when he doesn’t care for overdogs.

Disaster suits him.