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A founding member of the Monty Python crew, Terry Gilliam’s fantasy creations were often the most bonkers of the utterly bonkers comedy troupe, and would later evolve into a far-out, surreal filmography like no other. 

Born in Minnesota, Gilliam moved to London in the late 60s, defecting from America as a fuck you to the rising tide of authoritarianism in the US and police brutality, and naturalised to British citizenship in 1968. It’s here, in swingin’ London that Gilliam began working with the Python crew, creating brilliantly absurdist comedy. Beginning as the Python’s animator and illustrator for LPs and book covers, Gilliam’s responsibility soon evolved to full membership with co-writing credits, while his wacky animations would become a defining aspect of the group’s aesthetic.

Gilliam’s cinematic breakthrough came via Monty Python and the Holy Grail. Co-directed by Gilliam with fellow Python Terry Jones, the flick was an irreverent take on the King Arthur legend that included classic scenes like the Knights who say Nee, the Rabbit of Caerbannog and the never-beaten Black Knight. Blending historical and societal accuracy with visionary surrealism and sharp humour, this experience became a fundamental stepping stone in Gilliam’s M.O.

Via his world-building imagination, some of Gilliam’s finest works have come in the realm of science fiction, taking place in futuristic, dystopian landscapes – affording him the opportunity to forge bizarre, fantastic and horrifying worlds that reflect our own through a warped angle.

You can’t see the dystopian metropolis that populates Gilliam’s 1985 classic Brazil without considering the vast, ever-encompassing cityscapes of the world’s cities and the bureaucratic coldness that follows. Or the film’s portrayal of a society dominated by censorship and bureaucracy that presses on the wound of our own. Or even better, watch Gilliam’s time-travel sci-fi flick, Twelve Monkeys now –set around a devastating pandemic – and fresh poignancy is clear. Let’s all hope that prisoner James Cole (Bruce Willis) is currently racing through time to try and solve things like in the film – also starring Brad Pitt as a patient and animal rights activist locked in an insane asylum. Through these sci-fi worlds, Gilliam was able to confront and dissect societal topics of totalitarianism, machinery, and conformity (refer back to the reasons he left America mentioned earlier).

Speaking of surreal characters, now we come to Hunter S. Thompson’s role in Gilliam’s story, and the filmmaker’s cult adaption of the writer’s 1971 novel, Fear and Loathing in Las Vegas. A stream-of-altered-consciousness report of journalist Raoul Duke (read: Thompson) and his attorney Dr Gonzo on a trip to Las Vegas armed with an arsenal of hallucinatory drugs. Bringing the story to the big screen with help from stunning performances by Johnny Depp as Duke and Benicio Del Toro as Dr Gonzo, Gilliam shaped a world of psychedelic hedonism and danger that perfectly captured the madness of Thompson’s story.

Dealing with concepts of time, madness, technology and societal breakdown, 12 Monkeys was one of only several films Gilliam made on American soil – shot on location in Philadelphia and Baltimore in early 1995.

The plot centres around convict, James Cole (Bruce Willis), who is sent back in time from 2035 to discover the origin of a deadly virus which has wiped out most of the planet’s population and left the survivors taking refuge underground (above ground, the planet has been reclaimed by animals). Accidentally arriving in 1990 instead of 1996, Cole lands in an asylum where he meets inmate Jeffrey Goines (Brad Pitt), whose story intertwines with Goines’ mission.

With signature Gilliam plot twists and a future world that doesn’t look so foreign today, the work remains a crucial watch on the way to understanding Gilliam’s encompassing vision.

Bringing to life Hunter S. Thompson’s counterculture epic of the same name about his ‘true’ road trip story to Vegas with his psychotic lawyer and their mind-altering escapades that ensued, is no mean feat. Previous to Gilliam’s adaptation, both Martin Scorsese and Oliver Stone had tried to get the film off the ground with no luck, and it was only after many extensions that the production company finally landed on Gilliam.

With Johnny Depp playing Thompson’s alter-ego, Raoul Duke, (the two became close friends following this film and Thompson was the one who shaved Depp’s hair in his own image) and Benicio del Toro as his attorney Dr Gonzo, the madcap pair are brought to life in a tripped-out story riddled with nightmarish trips, surreal confusion and vivid lizard hallucinations. A master of the abstract, Gilliam perfectly captured that disorientating feeling of being uncomfortably high in a situation you shouldn’t be in, with camera shots vibrating between awkward angles, close-ups and transient swipes.

The film initially received mixed reviews from critics and was a financial failure, however, that was never the point: in ode to Thompson, here was a piece of work that stuck a middle finger up at commercial approval. Gonzo journalism had hit the big screen, and it was wild.

What to watch by Terry Gilliam:

• Fear and Loathing in Las Vegas, 1998
• Brazil, 1985
• 12 Monkeys, 1995
• Monty Python and the Holy Grail, 1975
• Jabberwocky, 1997