There are not many people working in cinema today that have an imagination as grand as Terry Gilliam. The American born auteur has now been directing films for nearly fifty years. He’s managed, in that time, to give us structured insights into the inner recesses of his mind, and craft some of the most beautifully wacky and hauntingly strange films to be released in mainstream cinema.

His creations are nearly always featuring a dreamlike world, though not like the mad, mad world of Quentin Tarantino, where everyone and everything is slick and cool. It’s a dreamlike world, where if you woke up from experiencing it, you’d be spending the rest of your life trying to figure out exactly what it meant. And you’d probably rack up some pretty hefty therapy sessions along the way.

Here, then, is a quick look at some of his most memorable films through the years.

Brazil

If you want the closest idea of what it must be like living in Gilliam’s head, then Brazil is the film for you. It was released back in 1985 and features Jonathan Pryce as a low-ranking bureaucrat, who is relentlessly searching for a woman who turns up in his dreams. It also has stellar performances by Bob Hoskins and Robert De Niro.

The main star of the show, though, is the dystopian setting that the story takes place in. The world has an unhealthy reliance on near-decrepit machinery, and is a masterful satire of technocracy, which feels like a mash-up of 1984 and a Kafkaesque nightmare. It will leave you thinking long after the credits have rolled.

Fear and Loathing in Las Vegas

Hunter S. Thompson was a writer who lived his life as if it was being watched through a kaleidoscope. So, when Terry Gilliam signed on to write and direct the adaptation of the writer’s magnum opus Fear and Loathing in Las Vegas, many people saw it as the perfect fit. Yet, when the film was released in 1998, it was a commercial failure, and it received extremely mixed reviews by critics. However, thanks to word of mouth and many people watching it first on video and then on DVD, it has now rightly become a cult classic.

The film stars Johnny Depp in the lead role, and he brings just the right level of deranged charisma to the part, bouncing off the equally fanciful, Benico Del Toro. The two cause utter chaos under the pretence of journalism, and ramble round Las Vegas on a debauched weekend. Gilliam sets the tone of the film perfectly, and brings the Strip of Las Vegas bursting out from the screen with its glittering lights and neon signs, that will make you want to visit the city right away.  

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12 Monkeys

This film was, perhaps, the first time that a director showcased the range that a young Brad Pitt was capable of. 12 Monkeys was released in 1995, and is a film about how a deadly virus has wiped out most of humanity and the survivors are forced to reside underground. Bruce Willis stars as the man sent back in time to try to stop the tragedy from ever happening. He meets Pitt on his journey, who plays a schizophrenic patient in a mental hospital, a role that earned him an Oscar nomination for Best Supporting Actor.

The film is a mystical rollercoaster ride that portrays a dripping feeling of dread, as the story twists and turns. Gilliam’s vision perfectly encapsulates the question, is humanity always destined to destroy itself?