Terry Gilliam is one of only a handful of directors who truly understands how to craft a great fantasy movie. His films combine a genuine sense of strangeness with a grand visual style, often with an added dose of surreal humour left over from his Python days. However, Gilliam has also had his fair share of production problems and box office bombs, while his new movie, the upcoming The Imaginarium of Doctor Parnassus, has been overshadowed by the tragic death of star Heath Ledger. Matt McAllister takes a look at 10 of Gilliam’s most interesting endeavours…

1) Brazil (1985)
Gilliam’s dystopian masterpiece was a flop on its initial US release back in 1985, but is now regarded as one of the most seminal SF movies ever made. Jonathan Pryce plays the hapless office administrator who unwittingly becomes an enemy of the authoritarian state, and there are memorable offbeat performances from Bob Hoskins, Robert De Niro and Michael Palin. Gorgeous to look it and frequently very funny.

2) Time Bandits (1981)
The much-loved Time Bandits sees an 11-year-old embark on a journey through space and time with a gang of seven dwarves. The adventures that follow include run-ins with Robin Hood (John Cleese) and Napoleon (Ian Holm) and a visit to the sinking Titanic. But this is no simple whimsical adventure, with the movie boasting one of Gilliam’s most disturbing endings. We’d kill to see the long talked about sequel…

3) Monty Python and the Holy Grail (1975)
Debate rages over whether the Holy Grail or Life of Brian is the better movie, but there’s no doubting the Holy Grail’s status as a comedy great. Containing thousands of quotable lines (“We are the Knights who say... NI!”, “She’s a witch, burn her!” etc etc) and a freewheeling narrative, the film has recently been adapted into the hit stage musical Spamalot. Gilliam co-directed the movie with Terry Jones, along with providing some of his unmistakable animation and appearing as King Arthur’s servant Patsy.

4) Twelve Monkeys (1996)
Gilliam held back on the Python-esque humour for this gripping reworking of Chris Marker’s La Jetée. Bruce Willis plays James Cole, a future convict who is sent back in time to retrieve information about a virus that will wipe out much of humanity. Brad Pitt slightly overdoes the tics as a mental patient that Cole is locked up with, but Willis gives one of his most intense performances as mankind’s last hope.

5) The Crimson Permanent Assurance (1983)
The Gilliam-helmed short film that precedes Monty Python’s The Meaning of Life is a funny, breathlessly inventive satire that turns its wonderfully odd premise into a mini-epic. An old-fashioned insurance firm rebels against its ruthless new corporate management by turning to piracy, transforming their office into a ship that sails down the Thames. Should be watched daily for the duration of the Credit Crunch.

6) Fear and Loathing in Las Vegas (1998)
Hunter S Thompson’s loosely plotted account of drugs, insanity and lounge lizards is the very definition of an “unfilmable” novel, but Gilliam manages to faithfully capture both the book’s events (we can’t quite use the word “plot”) and atmosphere. Johnny Depp and Benicio Del Toro are perfect in the roles of the perma-stoned Raoul Duke and Dr Gonzo, while Gilliam brilliantly recreates the fantastical, frightening world of their drug-induced, reality-warped state. It’s definitely a film of the love-it-or-hate-it variety (and many critics hated it on its initial release), but it’s also a true one-off.

7) The Fisher King (1991)
Another very different kind of fantasy from Gilliam, The Fisher King fuses the Grail legend with the story of an unusual friendship between Robin Williams’ homeless “knight” and tortured shock-jock Jeff Bridges. The film earned Mercedes Ruehl an Oscar for Best Supporting Actress, and proved Gilliam was able to create a more downbeat human drama, albeit in his own distinct way.

8) Jabberwocky (1977)
The first movie that Gilliam directed on his own is a quite brilliant mixture of Pythonesque comedy and ambitious fantasy. The film recreates the Middle Ages in all its squalid glory, while Michael Palin is charming as the clumsy unlikely hero, Dennis Cooper. On the DVD commentary, Gilliam is open about the movie’s faults - including the lack of funds to properly realise the Jabberwocky (though the effects still retain a certain lo-fi charm) - but the film remains an underappreciated gem.

9) The Adventures of Baron Munchausen (1988) (pictured)
A famously expensive bomb (even by Gilliam’s standards), Baron Munchausen has been reassessed as something of a cult classic in recent years. It’s not Gilliam’s best work, but contains numerous unforgettable, inventive sequences including Robin William popping up as the King of the Moon’s jealous flying head!

10) The Man Who Killed Don Quixote (1999/2010) / Lost in La Mancha (2002)
Gilliam’s biggest disaster to date was probably his attempt to film Cervantes’ Don Quixote in 1999. The film was beset by difficulties including devastating flash floods and its lead actor, Jean Rochefort, pulling out due to a double herniated disc. The film was eventually abandoned, but at least the crushing failure resulted in the hugely entertaining documentary Lost in La Mancha. Not one to admit defeat, Gilliam is now having another attempt at filming the novel, and is engaged in pre-prep on version 2.0. Let’s hope he actually gets to finish it this time…