No matter what their abundance might tell you, adaptations of classic novels can be tricky. What works best in one medium and what works best in another are seldom the same thing. The two are so different, their strengths and weaknesses so unique and specific, that perhaps the old adage is true: some novels are simply unfilmable. (For example, Cormac McCarthy’s Blood Meridian, which, until recently, James Franco has been threatening to adapt.) There are no rules to writing literary fiction and, of course, no ratings boards to sneak sex, drugs, and violence past. Yet, every now and then, a film comes along, defying logic and common sense to transform the impossible novel into the miraculous film.

Director Ben Wheatley‘s acclaimed adaptation of J.G. Ballard‘s classic entry in the catalog of the un-filmable, High-Rise, is now available on-demand and in select theaters this week. In the film, Dr. Laing (Tom Hiddleston) moves into a swank London high-rise apartment complex, which gradually devolves into class warfare and violent insanity as the occupants of various floors battle for control of the building. We recently spoke with Wheatley about the book’s so-called unfilmable nature, a description which he believes could be unwarranted.

“It just depends how you define unfilmable,” Wheatley says. “When you actually look at the book, it has quite a linear storyline to it, and it’s quite strong visually. The difficulty comes in the way the characters act. It doesn’t have a traditional happy ending, and the characters don’t act like traditional Hollywood movie characters do. But I think High-Rise has unfairly had this unfilmable tag just because it’s been in development for a long time. It doesn’t necessarily always mean the same thing. With High-Rise, it just means there’s not been an appetite for it up until now, not that it’s been impossible to film.”

Our review confirms High-Rise as “a masterpiece,” which inspired us to look back through the annals of cinema for the finest examples of films based on supposedly unfilmable novels. Check it out below, and suggest your own favorites in the comments.

Adaptation and Where the Wild Things Are (Spike Jonze)

A film that defies the notion of unfilmability, Spike Jonze‘s Adaptation offers a perfect window into the difficulties screenwriters encounter when attempting to turn a great book into an equally great movie. Adapted from The Orchid Thief, Susan Orlean‘s sprawling work of non-fiction by screenwriter Charlie Kaufman, it employs the novel’s themes and real-life characters in an utterly unexpected fashion, spinning them into a brilliantly blurry web of fact and fiction. Instead of merely focusing on Orlean’s characters, Kaufman writes himself into the screenplay as a screenwriter confounded at the prospect of adapting this unfilmable novel. Orlean herself initially balked at the film’s premise, which relegates her story to the B-plot as Kaufman’s own downwardly spiraling life takes center stage. Orlean expanded in an interview with GQ: “They told me that everybody else had agreed and I somehow got emboldened,” Orlean said. “It was certainly scary to see the movie for the first time. It took a while for me to get over the idea that I had been insane to agree to it, but I love the movie now.”

In The Child That Books Built, British author Francis Spufford described Maurice Sendak‘s Where The Wild Things Are as “one of the very few picture books to make an entirely deliberate and beautiful use of the psychoanalytic story of anger.” Indeed, that same sense of anger and adolescent frustration found its way into Spike Jonze‘s film, a painterly adaptation of Sendak’s already visually unforgettable work. It was considered unfilmable — perhaps due to its picture-book origins, in which a mere 338 words accompany Sendak’s haunting illustrations — yet Jonze and screenwriter-author Dave Eggers were inspired to craft this savage story a bit differently. Jonze’s film is a unique and often disturbing look at the loneliness and emotional growing pains of adolescence, told through the eyes of a kid with a robust imagination. It’s easy to forget that this charming children’s classic inspired a film that opens with that same kid chasing his dog down the stairs, brandishing a metal fork. If there was anything unfilmable about Where the Wild Things Are, Jonze and Eggers not only embraced these unsettling elements, but pushed them as far as they could.

American Psycho (Mary Harron)

Adapting Bret Easton Ellis‘ controversial novel to the screen presents more than a few problems for a hopeful screenwriter. For one, the novel’s liberal employment of graphic sex and shocking violence places any potential adaptation on the precipice of an NC-17 rating, which Mary Harron‘s film was indeed slapped with until a threesome was trimmed down. Ellis himself had initially been tasked to adapt his work, receiving notes from director David Cronenberg, who was, for a time, also attached, requesting that the book’s violence and restaurant scenes be excised from the narrative. This would have been like trying to adapt Harry Potter without including any magic or scenes at Hogwarts. Harron’s script, co-written with actress Guinevere Turner, brings the novel to hilarious life, portraying this animal in his natural environment — including much of Ellis’ violence and fancy restaurants lacking “good bathrooms to do cocaine in.” Perhaps American Psycho was deemed unfilmable because the book’s wry comedy of manners could have so easily been lost among the severed heads and endless sex scenes.

Apocalypse Now (Francis Ford Coppola)

Surely an entire book could be written detailing the various ways in which Joseph Conrad‘s Heart of Darkness proves an insurmountable feat for any screenwriter. There’s a brilliantly crafted full-length documentary (Eleanor Coppola, George Hickenlooper and Fax Bahr‘s Hearts of Darkness: A Filmmaker’s Apocalypse) that explores the hellish insanity burdening the production of Francis Ford Coppola‘s Apocalypse Now. Shot in the Philippines from an ever-evolving screenplay by John Milius (with narration provided by Full Metal Jacket co-scribe Michael Herr), the film’s finale was perhaps the Academy Award-winning director’s biggest struggle, as an early draft climaxed in what Coppola described disappointingly as “a macho comic book ending.” In the documentary, Coppola admits, and with the benefit of hindsight, “I knew when I arrived there that I was going to take John’s script and mate it with Heart of Darkness and whatever happened to me in the jungle.” To film the unfilmable, Coppola incorporated the very insanity that plagued the production, turning crippling disasters into unexpected opportunities. Look no further than Dennis Hopper‘s fiendishly poetic rantings, which are ceased by Col. Kurtz (Marlon Brando) angrily throwing a melon at him. Why do I get the feeling that Coppola wished he could be the one hurling that melon at the mischievous Hopper?

Catch 22 (Mike Nichols)

Every now and then, a supposedly unfilmable novel becomes such a fantastic film that the book’s author bestows the movie with his or her seal of approval. Such is the case with Mike Nichols‘ film of Joseph Heller‘s Catch 22, an absurd story of World War II bomber pilots drifting into desperation and surreality under the sweltering Mediterranean sun. According to the film’s DVD commentary (a must-listen as Nichols sits down with filmmaker Steven Soderbergh), Heller was so delighted with screenwriter Buck Henry‘s dialogue additions that he wished they could have been included in the book. A fine example comes when Milo (Jon Voight) informs Yossarian (Alan Arkin) that fellow pilot Nately (Art Garfunkle) died a wealthy man as a result of his sixty shares in the syndicate. Stunned, Yossarian barks, “What difference does that make? He’s dead.” Milo shrugs, “Then his parents will get the money.” In the novel, the exchange ends there, but Henry added two more eerily evocative lines of dialogue. Yossarian retorts: “They don’t need it. They’re rich.” To which Milo replies, “Then they’ll understand.”

Cloud Atlas (Tom Tykwer, Lana and Lilly Wachowski)

Even a cursory glance at the book’s description will offer a good indication of how difficult a task it would be to adapt David Mitchell‘s Cloud Atlas. Consisting of six nested stories that unfurl across a span of thousands of years with a top-notch ensemble cast each playing several different roles, it’s a story blending mystery, comedy, sci-fi, and action filmmaking into one towering tale. Directed by Tom Tykwer, Lana Wachowski, and Lilly Wachowski, it’s a project that sounds as if it should be the basis for a Jowdorowsky’s Dune-like documentary about a failure to attain funding. Thankfully, Cloud Atlas was made into a rip-roaring adventure story of the highest caliber, keeping us thrilled and engaged with each plot strand, no matter how bizarre. Tykwer and the Wachowskis may be painting with broad strokes, but they’re immaculately placed, enveloping their audience in the sweeping scope of this grand tale.

Life of Pi (Ang Lee)

Sometimes the word “unfilmable” gets tossed around too freely, which is the case with Yan Martel‘s Life of Pi. There’s nothing unadaptable about the narrative — as long as you have access to the greatest tiger-actor in the world. Perhaps I should explain: Life of Pi centers on Pi (Suraj Sharma), the lone survivor of a south Pacific shipwreck who finds himself confined to a lifeboat with only an adult Bengal tiger to keep him company. For years, the notion of filming this story seemed impossible due to the limits of CGI technology, a process often more adept at rendering life-like monsters than photo-realistic animals from our own world. But that was then. Ang Lee‘s Academy Award-winning film captured every tragic nuance of Pi’s Job-like ordeal, sentenced to drift alone into the vastness of the Pacific ocean. The novel’s twist in its third section, revealing the true nature of Pi’s time on the lifeboat, is never depicted onscreen, saving us the pain of witnessing such ugliness and sorrow. The reveal, that this is less a story about animals than it is a story about storytelling, hits like a devastating emotional sucker-punch. This lovely lie miraculously transforms the worst aspects of existence into a life-affirming 3D triumph.

Lolita and A Clockwork Orange (Stanley Kubrick)

Perhaps it was the censorial influence of the times that prevented Stanley Kubrick from fully exploring the unsettling depths of Vladamir Nabokov‘s Lolita. (In the film, Lolita is portrayed as being in her mid-to-late teens. In the novel, she’s barely twelve years of age.) In fact, Lolita is one of the rare examples of a great novel that may have definitively been proven unfilmable, as even a second attempt by filmmaker Adrian Lyne proved less-than-stellar. This is not to say Kubrick’s film is without its charms, as cast members James Mason, Sue Lyon, Shelley Winters, and Peter Sellers bring humor to their roles. However, Kubrick’s screenplay (although credited to Nabokov) throws out much of the novel’s darkness (a black comedy about a shameless pedophile) in favor of a cheekily mannered satire of gender relations. How did they ever make a film of Lolita? By intentionally not doing so.

When he later came to adapt A Clockwork Orange, Kubrick once again attempted to sand off the sharper edges from a story that as many readers had deemed unfilmable as other, lazier ones had deemed unreadable. Author Anthony Burgess‘ use of language in A Clockwork Orange remains as groundbreaking as ever, spinning his own vernacular from a mixture of Cockney and Russian, creating Nadsat, an ageless lexicon of teenage slang for his ruthless protagonists. In many ways, the novel’s brutality cuts even deeper than the film, despite the fact that Kubrick’s work has become rightly notorious for its unflinching depiction of rape and violence. As with Lolita, the fifteen-year-old Alex of the novel becomes the eighteen-year-old of the film, a revision altering the dangerously rebellious teen into a criminally insane adult. If you were to remove all of the Nadsat, you would be left with a rather straightforward narrative about the essential importance of free will. Hardly an unfilmable tome. It’s also funny to recall that Kubrick’s film of Burgess’ notorious novel isn’t even the first time the book was adapted for the screen. Legendary artist Andy Warhol made a loopy, unwatchable version (unless you’re a hardcore Warhol devotee) in 1967, which many say inspired Kubrick’s opening close-up shot of Malcolm McDowell‘s Alex.

Naked Lunch (David Cronenberg)

David Cronenberg had his work cut out for him when he agreed to adapt William S. Burroughs‘ Naked Lunch. Throwing out the legendary cut-up novel’s fractured structure in favor of blending real events from the author’s life with the book’s themes and locales, Cronenberg found a wry understanding of the text through an understanding of Burroughs himself. Bill Lee (Peter Weller) is an exterminator-writer who drifts into addiction and sexual ambivalence in the foreign land of Interzone after accidentally killing his wife (Judy Davis) during an intoxicated William Tell routine. As hallucinations overtake Lee’s world, his typewriter morphs into a massive beetle (complete with a flapping, talking anus) and the population slowly becomes hooked on “Mugwump jism.” In so many words, Cronenberg transformed Naked Lunch into a David Cronenberg movie, complete with a beautifully toned jazz score by Howard Shore and Ornette Coleman, which often sounds akin to someone practicing the trumpet in an apartment down the hall, sadly distant and gorgeously haunting. By the film’s finale, we understand all too well what Lee meant when he advised his cohorts to “exterminate all rational thought.”

Never Let Me Go (Mark Romanek)

Perhaps Never Let Me Go was deemed unfilmable in terms of the novel’s devastating emotional impact. Even director Mark Romanek and screenwriter Alex Garland were unable to adapt the book without resorting to long stretches of voiceover narration conveying the interior thoughts and emotions of Kazuo Ishiguro‘s protagonists. Despite this arguable narrative crutch, the resulting film is a tender elegy to innocence lost and never regained, anchored by powerful turns from Carey Mulligan, Keira Knightly, and Andrew Garfield. It’s a heartfelt story of the students of Hailsham boarding school who come to learn they will be tragically robbed of their adulthood. While I’ll avoid revealing the film’s secrets here, to say that these poor kids are not only doomed, but purposefully intended for a life of pain and misery would be a mournful understatement. As heartbreaking as its climax may be, Never Let Me Go proves a moving exploration of the human heart’s resilient endurance even under the most hopeless of conditions.

Tristram Shandy: A Cock and Bull Story (Michael Winterbottom)

I suppose many readers deemed Laurence Sterne‘s The Life and Opinions of Tristram Shandy, Gentleman unfilmable due to its length and seemingly infinite narrative digressions. Understandably so. The novel is, in part, about the creation of its own protagonist, Tristram, whom by the end of the book’s second volume has yet to be born. As well, director Michael Winterbottom adapts the film into a story of its own creation in a half-mockumentary style, weaving a different story about actor Steve Coogan attempting to portray Shandy with his ever-present comedic-foil Rob Brydon playing Uncle Toby. Early on, Shandy wonders aloud: “Am I not the lead character of my own story?” Not necessarily. By the end of shooting, it’s revealed that Brydon will have more screen-time in the film than Coogan, a blow to the arrogant actor’s ego. Indeed, if a novel is truly unfilmable, then why not simply adapt the tone and feel– the sense of whimsical absurdity? Winterbottom’s film is a sheer delight for both fans of the novel and newbies alike, proving that self-indulgence can indeed be an art form.

High-Rise is now on VOD and hits theaters on Friday, May 13.

What are your favorite supposedly “unfilmable” adaptations? Which books would you like to see turned into features?