Books and films have been joined at the hip ever since the earliest days of cinema, and adaptations of novels have regularly provided audiences with the classier end of the film spectrum. Here, the Guardian and Observer's critics pick the 10 best

Class act ... a scene from the 1968 film version of Planet of the Apes, starring Charlton Heston. Photograph: Ronald Grant Archive

Although the source novel, La Planète des Singes, was written by Frenchman Pierre Boule and originally reached its futureshock climax in Paris, this enduring sci-fi fantasy is profoundly American, putting Charlton Heston's steel-jawed patriotism to incredible use. It also holds up surprisingly well as a jarring allegory for the population's fears over escalating cold war tensions.

Beginning with a spaceship crash-landing on an unknown planet after years of cryogenic sleep, Franklin J Schaffner's film soon gets into gear as Heston's upstanding astronaut Taylor is chased and seized by a troop of gorillas on horseback. Saved for "research" purposes, Heston is taken to a city ruled by apes. Luckily for us, producer Arthur P Jacobs resisted Boulle's epic, futuristic vision of the future for budgetary reasons, and his penny-pinching surely saved the film from dating instantly. There are still some hippyish Age-of-Aquarius flourishes in the ape costumes, but the primitive architecture, somewhere between Greek and Roman, ominously anticipates the film's killer twist, which sprang not so from Boulle but the Twilight Zone's Rod Serling, who refined the shooting script.

Interestingly, for a film based on a single idea, it is the sum of its parts that make it so timeless – principally Jerry Goldsmith's eerie, organic score – while the cast makes easy work of ensuring the apes are simultaneously terrifying and, in the case of in Kim Hunter and Roddy McDowall as Zira and Cornelius, incredibly sympathetic. Crucial to this is the film's staggering make-up, so ahead of its time that prosthetics artist John Chambers had to make do with an honorary award at that year's Oscars since special effects had yet to be deemed worthy of a category. Luckily, his handiwork was so good, he didn't have to wait long for another job, and he was swiftly tapped up by a grateful new employer: the CIA. (Yes, that's him as impersonated by John Goodman in Argo.) Damon Wise

RALPH RICHARDSON AND BOBBY HENREY IN A STILL FROM THE FILM THE FALLEN IDOL (UK 1948) BRITISH LION FILM CORP Photograph: Ronald Grant Archive

Graham Greene went to his grave justifiably disappointed in the many movie adaptations derived from his novels. The Comedians, The Honorary Consul, The Human Factor, the first adaptations of The Quiet American and The End of the Affair: all of these fell short, or actively betrayed their source-novels. One of the fascinating conundrums of Greene's career is that this highly perceptive former film critic, fitfully brilliant screenwriter and author of so many novels dubbed "cinematic" should have suffered so badly at the hands of filmmakers, particularly in Hollywood.

The few successful films of his work tended to be adapted by Greene himself and/or made in Britain: John Boulting's Brighton Rock, Alberto Cavalcanti's Went the Day Well? and the long-unseen The Fallen Idol, which Greene and director Carol Reed made in 1948, a couple of years before they embarked on the worldwide hit that was The Third Man. Freely adapted from Greene's 1935 story The Basement Room, The Fallen Idol follows Philippe (Bobby Henrey), the 7-year-old son of the French ambassador in London, who stumbles onto the adulterous affair between his father's valet Baines (Ralph Richardson) — the eponymous object of his worship — and Julie, an embassy secretary (Michele Morgan).

As pregnant with secrets and lies as any of Greene's spy stories, The Fallen Idol is also one of the great movies about childhood innocence accidentally violated by adults, harking back to Greene's literary idol Henry James' What Maisie Knew, and forward to LP Hartley's The Go-Between (whose 1970 adaptation by Joseph Losey is one of the great movies of its period). Reed, an often inconsistent film-maker, handles the brutal mechanics of the plot superbly, with the marbled interiors of the embassy contrasting sharply with his almost neo-realist outdoor shots of postwar London. John Patterson

Elliott Gould in The Long Goodbye. Photo: Sportsphoto Ltd/Allstar

Robert Altman developed his version of The Long Goodbye as the story of "Rip van Marlowe" – what happens when the 1940s private dick is dropped into a 1970s Los Angeles he would barely recognize as home. Instead of Humphrey Bogart of The Big Sleep, he's now the unbuttoned, floppy-haired Elliott Gould. Instead of dealing with sharp-tongued women in pin curls and shoulder pads, he's working for a Malibu housewife in a big sun-dress and bare feet. By updating Marlowe's environment but not his personality, Altman reinvents the man for the 1970s, a detective whose wit and skills can't be diminished by a world far more corrupt than he.

Altman and screenwriter Leigh Brackett take immense liberties with Raymond Chandler's source novel, inventing entire characters (like the vicious Marty Augustine) and eliminating major ones, like Sylvia Lennox's billionaire father. Though Altman and Brackett borrow the basic structure of the novel, The Long Goodbye is essentially a riff on Chandler's entire work and his influence on film. It's a revisionist noir that manages to bring one of the genre's biggest icons in on its scheme, both thumbing its nose at and revering the beloved private detective.

Marlowe is hilariously out of step with his surroundings here, shuffling around his space-age apartment building and muttering at the hippie chicks doing yoga next door. But he's still the hero, the only man who cares enough to give Terry Lennox the justice he deserves, the guy who shrugs off a violent gangster to keep looking for his missing cat. The world has gone madder than Chandler ever imagined, but Marlowe proves he can stand the most difficult test of time – and he never has to give up his cigarettes or his 1948 Lincoln Continental to do it. Katey Rich

James Mason and Sue Lyon in Stanley Kubrick's film of Lolita (1962). Photograph: Ronald Grant Archive

Stanley Kubrick once said that if he'd known how much trouble it was going to get him into, with various censor bodies and religious pressure groups, he would never have made Lolita. It says something about our changing world that even though censorship has relaxed a lot in the last 51 years, Vladimir Nabokov's hot-button novel would now be thought even further beyond the pale than ever. Indeed, it's quite incredible that one of the few compromises the exacting Kubrick had to make was to raise the age of his young heroine from Nabokov's 12-and-a-half to a somehow more permissible 14.

But if it seems surprising that the thought police have left Kubrick's film alone in this jittery post-Yewtree world, in retrospect Lolita seems surprisingly future-proof. Although primarily identified as a director of cool, detached spectacle movies, Kubrick also had a rich sense of dark, sardonic wit, and the dry comic elements of Lolita ensure that the film cannot be misinterpreted. Hinting at the broad humour that would spill out in Dr Strangelove and A Clockwork Orange, Kubrick's Lolita is best read as a satire of male desire, with Sue Lyon's title character becoming the focus of the pitiful Humbert Humbert's midlife crisis.

As Humbert, James Mason's musical, gentrified tones go a long way to ensuring that the film retains some decorum, even while the infatuated professor goes through with a sham marriage to the girl's widowed mother (a nicely contrasting camp performance by Shelley Winters). But the standout is perhaps a small but pivotal role by Peter Sellers as Humbert's nemesis, the chameleonic Quilty – a sleazy playwright who also vies for Lolita's affections. Although it is often seen as a precursor to the multiple parts played in Dr Strangelove, Sellers' turn here is a reminder of his true potential, soon to be swallowed up by a stream of ever more awful Pink Panther films. DW

'Courageously uningratiating': Tilda Swinton and Jasper Newell in We Need to Talk About Kevin.

In Lynne Ramsay's meticulously controlled adaptation of Lionel Shriver's novel, we only glimpse the odd drop of blood. That's quite an achievement given that the pivotal event is a high-school massacre. Having resolved not to show what happens when 15-year-old Kevin (Ezra Miller) begins picking off his schoolmates with a crossbow, Ramsay crams her film instead with proxy horrors and surrogate scares. Red paint is used in revenge attacks against Kevin's mother Eva (Tilda Swinton). Revellers caked in tomato pulp at Spain's La Tomatina festival stand in for the victims of the massacre. Red is everywhere. One shot even shows Eva sipping claret while a red teddy bear lies face-down in exasperated despair.

Readers of Shriver's novel will have been divided between those who saw the character as an uncomplicated monster, and those who distrusted his mother's control of the narrative. It's this tension which the picture exploits skilfully: Ramsay's screenplay dispenses with the format of the book, which was structured as a series of letters from Eva to her husband Franklin, and with chronology itself. Plus the movie is expertly cast. Swinton is physically sharp and snappy, moving as though she has scissor blades rather than bones under the skin. This lends her a kinship not with the doughy John C Reilly, as Franklin, but with Miller as Kevin. Both actors have forks of black hair and angular, androgynous profiles; at least one sequence intercuts their faces to suggest that the characters are interchangeable.

Ramsay has made a surprisingly playful adaptation invoking horror-movie mannerisms one moment, then socking it to us the next with bravura sequences. Among them is the Diane Arbus-esque highpoint: a nocturnal drive through the suburbs on Hallowe'en where masked trick-or-treaters lurch at the car windows. Ryan Gilbey

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Moviestore Collection/REX (1578516a) Ivansxtc, Danny Huston Film and Television FILM TELEVISION IVANSXTC DANNY HUSTON Film Stills Personality 12234543 Photograph: Moviestore Collection/REX

Leo Tolstoy and Bernard Rose go way back. The British director was once barred from the editing suite where his adaptation of Anna Karenina was being butchered. Perhaps it is a kind of revenge that Rose then took another Tolstoy work — The Death of Ivan Ilyich — and did it resolutely his own way. Ivansxtc (pronounced "Ivan's Ecstasy"), the first of four low-budget Tolstoy adaptations which Rose shot on high-definition digital video, tells of hedonistic Hollywood agent Ivan Beckman (Danny Huston), a know-it-all who doesn't even know himself. "I draw the line at smack," he says solemnly when discussing his habit. A moment later he changes his mind. "Maybe I'll try it. Smack is great!" One inspiration was Rose's own former agent, the wheeler-dealing Jay Moloney, who hanged himself three years after being sacked from the mighty CAA.

Ivan's eventual death is from lung cancer. But as befits a film inspired by Tolstoy, Ivan's true malaise is not physical but spiritual. This is a world of stretch limousines longer than the California coast, and lines of cocaine longer than stretch limousines. The characters, including a film-maker who attends Ivan's funeral because it is the only way he can corner the agent who has been dodging his calls, are fully formed and keenly observed. As Don West, an A-list superstar with a vampiric sexual appetite, Peter Weller gives the sleaziness a focus. He is more chillingly robotic than he ever was in RoboCop: at least in that movie you could sense the humanity behind the metal husk. Rose does not push the point, but West could be a metaphor for Hollywood itself—West as in West Coast, perhaps? There is nothing behind this demon's carnivorous desire but more carnivorous desire. In Rose's film, on the other hand, you can feel pity, disgust and compassion. RG

Screenwriter Charlie Kaufman (Nicolas Cage) develops a serious case of writer's block in the comedy Adaptation. Photograph: AP

In the late 1990s Charlie Kaufman was commissioned to write an adaptation of The Orchard Thief, a non-fiction book by Susan Orlean. But Kaufman was blocked, he couldn't find a way through, and so he tore up his draft and wrote Adaptation instead. He wrote himself as the star, concocted a fictional brother called Donald and then, magnanimously, found a supporting role for Orlean as a kind of lusty Lady Macbeth who snorts narcotics, sleeps with her subjects and plots the bloody death of her enemies. Orlean leafed through the script in a state of mounting confusion. "The idea of being portrayed as a drug-snorting mess just didn't square with me," she would later admit.

Adaptation doesn't particularly square with anything and that's what makes it great. It's a Houdini act, a feat of escapology; a freestyle theory on the creative process in which the avoidance and the struggle becomes the story itself. It helps, of course, that the film is as funny as it is self-referential. Kaufman shrewdly elects to puncture the angsty posturing of Charlie by having Donald beavering away on a trash thriller called The Three in which a serial killer suffering from multiple personality disorder effectively winds up in pursuit of himself. Naturally Charlie is disgusted; he wants to take the high road. But his own script's going nowhere and he gets lost in the swamp. Does Adaptation lose its way in these frantic final moments, when the cars flip over, the alligators gather and the body count mounts? Emphatically not - it is all of a piece, the last magic trick. When Charlie is unable to bring his tale to a close, it is left to Donald to throw himself into the mix and send us out with a bang. Xan Brooks

Brokeback Mountain

Ennis Del Mar and Jack Twist are a pair of straight arrow cowboys who take a job herding sheep and have sex on the hillside when the sun goes down. Jack and Ennis love each other and want to be together, but they can't bring themselves to admit this because their love is unthinkable. Later they will both marry and have children and lead conventional lives that feel somehow straitened and false. Brokeback mountain was a dream, although it shines more bright than the reality which follows.

Ang Lee's 2005 romance stars Heath Ledger and Jake Gyllenhaal, while the Oscar-winning script was penned by Diana Ossana and Larry McMurtry. It is based on a short story by E Annie Proulx, slender and heartfelt, a tale that covers the ground with the lightest of steps. The film has the same spirit, the same yearning, the same beautiful breadth of vision. It sketches the life-spans of two men, lived largely in the shadows. On its theatrical release, Brokeback Mountain found itself billed as "the gay cowboy movie", although debate has since ranged on its true orientation. Some critics argued that the characters would be better described as being bisexual, on the borderline, with Ennis shading right and Jack Twist leaning left. But I'm not sure that it matters. Brokeback Mountain is able to rise above such labels, even as its characters twitch and struggle and feel imprisoned by them. It is a film about the love that liberates and the fear that inhibits - and about that one golden summer that gallops into the past. XB

Jean-Louis Trintignant (as a fascist assassin) and Stefania Sandrelli in The Conformist. Photograph: Allstar/Cinetext/MARAN FILM

His reputation has receded over the horizon somewhat since his death in 1990, but in his day Alberto Moravia was a quintessential intellectual European novelist, patrolling the moral lines along which politics, which for him meant fascism, class, particularly the idle bourgeoisie he came from, religion, and transgressive sexual behaviour all intersected, at great cost to his characters. Many of his novels were international bestsellers, and several were adapted by big-name directors. These included Two Women by Vittorio da Sica, Contempt by Godard, and Boredom, adapted by Damiano Damiani in 1962, and remade by Cedric Kahn in 1998.

But Bernardo Bertolucci's adaptation of Moravia's 1951 novel Il Conformista stands above them all as a lasting achievement in international cinema, and as the pinnacle of Bertolucci's career. Its account of the neuroses and self-loathing of a sexually confused would-be fascist (Jean-Louis Trintignant) aching to fit in in 1938 Rome, who is despatched to Paris to murder his anti-fascist former college professor, was deemed an instant classic on release.

It was, and is, a highly self-conscious and stylistically venturesome pinnacle of late modernism, drawing from the full range of recent Italian movie history: a little neo-neorealism, a lot of stark and blinding Antonioni-style mise-en-scène, some moments redolent of Fellini. And it was all framed within an evocation of the frivolous fascist-era film-making style derided by Bertolucci's generation as "white telephone" cinema. Add a dose of unhealthy sexual confusion and nudity aplenty, and it's hardly surprising that it was one of the international hits of the year.

Certain sequences linger long in the memory: the brutal murder of the professor in a snowbound forest; the all-white lunatic asylum where Clerici meets his mad father; and an astonishing dance sequence with Domininque Sanda and Stefania Sandrelli in (and out of, and back into) a glass dancehall (a foretaste of Last Tango) It also offered the blueprint for the new wave of Hollywood film-makers to a different kind of cinema and a roadmap of new formal possibilities. JP

Jack Nicholson as Randle McMurphy in One Flew Over the Cuckoo’s Nest (1975). Photograph: Roland Grant Archive

Grinning and jeering, movie history's most troublesome psychiatric patient Randle "Mac" MacMurphy grabs the shower head in the Tub Room and sprays it like an anarchic water cannon. He's not attacking the nurses or the doctors – but his fellow patients, the ones who need waking up, the ones who consent to being docile prisoner-patients and who've made their own jail.

Milos Foreman's One Flew Over The Cuckoo's Nest (1975) is adapted by Bo Goldman and Lawrence Hauben from the 1962 novel by Ken Kesey, via a Broadway version by Dale Wasserman staged one year after the book's publication starring Kirk Douglas, whose son Michael produced the subsequent movie version and had the difficult task of explaining to Kirk that he now wanted someone younger for the film. It is a counter-cultural nightmare which retains its power to shock. Who hasn't had the nightmare or masochistic fantasy of somehow wrongly ending up in a psychiatric hospital and realising that every panicky thing you would then do — scream, plead, rage, desperately mimic the mannerisms of sanity that would otherwise come naturally — would of course be interpreted as madness? And would, in time, become madness? Jack Nicholson plays Mac, a natural born troublemaker and backtalker doing time for statutory rape. ("She was 15, going on 35.") He has been handed over to the psychiatric authorities under suspicion of faking madness to get out of jail and into a cushy mental facility. But this sinister place, with its drugs, muzak, electro-convulsive shock therapy and surgical intervention, is like jail but worse. One of the women Mac later sneaks in points out another depressing resemblance: "This looks like my high school!" Only a crazy person would pretend to be crazy to come here. Far too late, Mac realises the Catch-22. As Mac gets to know his fellow patients, including Martini, played by a young Danny DeVito and Chief Bromden (Will Sampson) a huge Native American who never speaks, it becomes his burden to symbolise pure craziness and wildly defiant opposition to the label of craziness. Cuckoo's Nest is very similar to prison-break movies like The Great Escape and Cool Hand Luke, or even military movies like Full Metal Jacket; but Mac has not been drafted or imprisoned as such. He is astonished to realise that he is one of the very few people actually forced to be there: the rest are voluntary in-patients who have become institutionalised. Prison or war movies take place in a sweaty male world, but these disturbed guys are surrounded by delicate women: nurses, particularly the cool and headmistressy Nurse Ratched, played by Louise Fletcher: a sharp-tongued high priestess dispensing tranquilliser drugs in a sort of holy communion ceremony. In fact, she is not the two-dimensional sadist of repute. In a medical conference, Ratched is shown discussing Mac's case with what appears to be interest and compassion. It is she who fatefully tells the hospital director he should be kept in the hospital and not returned to prison as a faker. But is that simply due to her insidious clinical urge to subdue and suppress? From the first, Mac flirts with and needles Nurse Ratched; he challenges her authority. He organises basketball sessions, demands time away from group-therapy to watch TV sports; it is cheerful Mac who improves the patients' morale and he even (briefly) cures the stammer of a gentle, vulnerable kid by getting him laid. It's not simply that Mac is the only sane person in a world of madness. He is the only functioning doctor. But was Mac pretending to be crazy in any case? Cuckoo's Nest emerged at a time when RD Laing's anti-psychiatry theories were current. Mac points to a patient and shouts: "You're no crazier than the average asshole walking around in the street!" to which Nurse Ratched icily replies: "A very challenging observation." Anglo-American academe was absorbing the works of Michel Foucault who argued that prisons, asylums and hospitals were all constructed by the west's punitive need for surveillance and control — all in the name of rationalism. In fact, Foucault contrasted the prison-hospitals of the Enlightenment with a medieval world in which mad people roamed as free as in Sebastian Brant's 15th-century satire Ship of Fools. It's very like the jolly fishing expedition Mac organises for his new friends by stealing a boat and sailing around in a carnival spirit with his crazy crew, and even triumphantly catching a few fish, before they are all caught and herded back inside. Before that, Mac had pinched a bus, and driven his disciples around in that — very like Ken Kesey himself and his merry pranksters in the 60s Magic Bus, immortalised in Tom Wolfe's The Electric Kool-Aid Acid Test. In Foreman's later movie Amadeus, the lunatic asylum was a wretched place of despair, presided over by the self-hating Salieri, crooning from his wheelchair: "Mediocrities everywhere … I absolve you … I absolve you …" But that isn't exactly how Foreman sees the hospital here. The guilty parties are not the patients but the malign dullards of the courts and the medical establishment, more culpable even than poor Nurse Ratched himself whose own spite is a simple and rather human failure to exert control after Mac organises a chaotic party. This film is not a horror film or a Gothic fantasy, although with its creepy whitewalled colour scheme and sinister affectless calm it has the look of a futurist sci-fi. Despite its occasional stagey and verbose tendencies, it is compelling and absorbing — and it has a factual base. After all, Rose Kennedy, sister of John F Kennedy, had a lobotomy performed on her at the age of 23 because her father Joe decided her behaviour was unstable. Was she just spirited? Rebellious? Who knows? One Flew Over the Cuckoo's Nest is a mordant, painful and intensely subversive film. Peter Bradshaw

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