Cameras in pursuit of the unfilmable: Hollywood's impossible dreams

Some of our greatest stories have always defied movie directors – but a few are finally being realised on screen.

Stanley Kubrick described it as the "most chilling and believable account of a warped mind" he'd ever read. And yet The Killer Inside Me, a crime novel published in 1952, has defied Hollywood film-makers for more than half a century.

The British director Michael Winterbottom has now finally brought a shockingly violent version to the screen. Starring Casey Affleck and Kate Hudson, it has received mixed reviews, mainly due to its gruesome portrayal of murder.

It is the latest of a small number of literary works – long considered "unfilmable" – that are making it to the screen. Shooting for Salman Rushdie's Midnight's Children, a sprawling magical-realist take on the birth of India, will begin in September. In December, Jack Black's modern-day revision of Gulliver's Travels – a novel that has long defied serious film-makers because of its arcane political satire – will be released. Life of Pi, Yann Martel's tale of a boy stranded in a lifeboat with a tiger, was also due to be turned into a CGI epic, but was shelved last week after Brokeback Mountain director Ang Lee presented his $70m (£48m) script.

For film producers, adapting best-selling books guarantees instant recognition which, it is hoped, translates to box-office sales. But for screenwriters, the best-seller is a potential nightmare. There are fans who expect films to be accurate translations of their favourite novel. Other books, such as The Lord of the Rings, have flummoxed Hollywood because of their length.

Other problems include translating tone, metaphor and subtlety – not something at which Hollywood always excels. And then there are books, such as William Burroughs's Naked Lunch, so devoid of narrative structure that there is little for a screenwriter to get to grips with.

William Boyd, the British author and screenwriter who was berated for excising chunks from his adaptation of Evelyn Waugh's Scoop in 1987, said films should be judged on their own merit. "To judge a film by the book it's based on is very harsh," he said. "Nobody goes to see Verdi's Falstaff and goes home and reads The Merry Wives of Windsor. Nobody berates Verdi for leaving out so much of the play. And that should apply to film as well. When you adapt a book for film, you lose 60 or 70 per cent of it."

Claire Monk, a senior lecturer in film studies at De Montfort University and a member of its International Centre for Adaptations, pointed out that most films are adaptations of other source material rather than original scripts – but these often come with barriers to the film-maker.

"Obviously you can't film a book verbatim, unless your film is going to be seven hours long," she said. "And the film industry tends to assume that audiences want straightforward narratives. Nothing is intrinsically unfilmable, however. The issue is more how we go about filming particular books. Technology is also important – as in The Lord of the Rings. Martin Amis's Money is a good example of a book that has a level of satire and tone that didn't come across in the adaptation."

Don Quixote

Cervantes' rambling 1605 tale about a misguided knight errant has seen many attempts at filming it, including failed productions by Orson Welles and Terry Gilliam.

Unfilmability factor: 4/5

Life of Pi

Yann Martel's 2001 Booker Prize winner has defied all comers. Ang Lee tried but, when he showed his $70m script last week, the film was shelved.

Unfilmability factor: 4/5

The Catcher in the Rye

There has never been a film version of one of the 20th century's landmark books because the author J D Salinger refused to sell the rights.

Unfilmability factor: 5/5

A Confederacy of Dunces

John Candy, John Belushi, Will Ferrell and Steven Soderbergh have all tried to film John Kennedy Toole's novel.

Unfilmability factor: 5/5

Cat's Cradle

Richard Kelly, the man behind Donnie Darko, adapted Kurt Vonnegut's book in 2005, but it was dropped. Another version is due next year.

Unfilmability factor: 4/5

The Killer Inside Me

Jim Thompson's cult novel is told from the point of view of a psychotic deputy sheriff. It had defied many attempts to film it, though one did appear in 1976 with Stacy Keach. Michael Winterbottom's new version is about to open.

Unfilmability factor: 3/5

Critics: 3/5

Watchmen

Alan Moore's groundbreaking graphic novel about superheroes on the run spent 15 years in development hell until Zack Snyder came along and made a visually stunning but confusing film last year.

Box Office Mojo: 3/5

Unfilmability factor: 4/5

Critics: 2/5

The Lord of the Rings

Some would say Tolkien's dense three-volume epic, published in 1954-55, is unreadable, never mind unfilmable. Peter Jackson turned it into the fourth highest-grossing franchise of all time.

Box Office Mojo: 5/5

Unfilmability factor: 3/5

Critics: 5/5

Where the Wild Things Are

Producers wondered for 40-odd years how to make a film out of Maurice Sendak's 1963 children's book that had only 338 words. Spike Jonze and Dave Eggers had a go last year, but boy, it was depressing.

Box Office Mojo: 5/5

Unfilmability factor: 5/5

Critics: 5/5

Revolutionary Road

Richard Yates's novel was picked up by Hollywood almost immediately after its publication in 1961, but it wasn't considered commercial. Eventually, in 2008, Sam Mendes brought it to the screen with Leonardo DiCaprio and Kate Winslet.

Box Office Mojo: 4/5

Unfilmability factor: 2/5

Critics: 3/5

Gulliver's Travels

Previous adaptations turned Jonathan Swift's 1726 parody of politics and human vanity into a children's story. Later this year, Jack Black, Emily Blunt and Catherine Tate will have a go.

Unfilmability factor: 1/5

Money

Martin Amis's sharp satire of 1980s greed is not just complex but also admired for its subtlety of tone and language, which many have thought wouldn't translate to the screen. The BBC had a go last month with Nick Frost as John Self – to somewhat mixed reviews.

Box Office Mojo: 2/5

Unfilmability factor: 2/5

Critics: 2/5

Perfume

For years, Patrick Süskind refused to sell the rights to his 1985 book about smell and identity, arguing that only Stanley Kubrick could do the material justice. He relented and in 2006 the most expensive German film ever made opened to mixed reviews.

Box Office Mojo: 3/5

Unfilmability factor: 4/5

Critics: 3/5

Catch-22

Joseph Heller's anti-war satire was a hit on publication in 1961. It proved difficult to translate to screen due to its multi-character viewpoints and non-chronological style. A 1970 adaptation was a flop.

Box Office Mojo: 1/5

Unfilmability factor: 4/5

Critics: 1/5

LA Confidential

James Ellroy's crime novels rarely find their way on to the big screen because of their complexity. There were doubts about LA Confidential, but two years of scriptwriting and eye-catching performances from relative unknowns Guy Pearce and Russell Crowe made the 1997 film a hit of the decade.

Box Office Mojo: 4/5

Unfilmability factor: 3/5

Critics: 4/5