1. Tristram Shandy: A Cock And Bull Story (2006) Many books’ reputations as being “unadaptable” for the big screen stem from structural or voice idiosyncrasies that don’t translate to film’s more straightforward narrative style—though that hasn’t kept ambitious/foolhardy filmmakers from giving it the old college try, with varying degrees of success. Laurence Stern’s The Life And Opinions Of Tristram Shandy, Gentleman, published in nine volumes over the course of nearly a decade in the mid-1700s, was long upheld as the epitome of an unadaptable novel, not just for its length, but for its non-linear, digression-filled structure and 18th-century-specific cultural and textual reflexiveness. The lone big-screen adaptation of Stern’s novel, Michael Winterbottom’s 2006 Tristram Shandy: A Cock And Bull Story, gets around the novel’s problematic reputation by building a movie around that reputation, a film that’s an adaptation only in the most meta sense. A sorta-mockumentary centered on the modern-day filming of a Tristram Shandy period adaptation starring Steve Coogan as both himself and the titular gentleman in the film-within-a-film, A Cock And Bull Story takes great pains to both tell and show its audience, numerous times, how and why its source material is a terrible choice for an adaptation. (“He wants realism? I’m a grown man, talking to a camera, in a fucking womb.”) As the fake Tristram unravels onscreen, A Cock And Bull Story succeeds in expressing the novel’s essence, if not its content, which is appropriate for, as Coogan puts it, “a post-modern classic written before there was any modernism to be post about.”
2. Slaughterhouse-Five (1972) Kurt Vonnegut’s Slaughterhouse-Five throws together a special set of challenges that make it seem impossible to successfully adapt. Vonnegut spends much of the novel watching the quieter parts of World War II alongside Billy Pilgrim, who’s truly an antiwar hero in his childish, bumbling naïveté. Moreover, Pilgrim has become “unstuck in time,” experiencing his life out of order, sometimes repeatedly; structurally, the novel is a nonlinear narrative presented linearly. He also spends time in a zoo on the planet Tralfamadore. The biggest challenge, though, is what to do with the narrator, set up as Vonnegut himself: His beautifully plain language throws inevitable death against everyday banality, injecting a sad peacefulness into the novel’s tone. In keeping remarkably close to the source material, though, screenwriter Stephen Geller and director George Roy Hill succeed where many Vonnegut adaptations fail. They eliminate the narrator and put the camera in his place, exposing Billy’s point of view and creating a quick shorthand for his time-traveling by cutting to similar shapes, settings, or objects. The film stumbles between times as deftly as Pilgrim does in the novel, and by the time Pilgrim is abducted to outer space, it feels obvious, inevitable, and hopeful.
3. Naked Lunch (1991) Anyone who’s read Naked Lunch would have a hard time describing what, if anything, happens in William S. Burroughs’ most famous novel. There’s the Interzone. And Dr. Benway. And more than a few references to jism. But action of the sort that could be translated into a film? That’s harder to come by. It is, however, an unforgettable book, filled with incomprehensible passages—some of them created by cutting up sentences and pasting them together—but also dazzling setpieces and impressionistic details taken from Burroughs’ life as a world-traveling junkie in the years after he accidentally killed his wife in a drunken reenactment of the William Tell legend in Mexico. A longtime fan of the author, David Cronenberg emphasized the biographical connections in his adaptation, casting Peter Weller as a Burroughs stand-in and letting fact, fiction, and fantasy mix freely in a film set both in the post-war New York that gave birth to the Beat movement, and the dark, Mugwump-haunted reaches of the author’s psyche. It makes only a little more literal sense than the source material, but as a lyrical fantasia on Burroughs’ life and obsessions, it does right by its inspiration.
4. Fast Food Nation (2006) A straightforward adaptation of Eric Schlosser’s investigation into how dependent we’ve become on the not-so-nutritious food of McDonald’s and other franchises would probably leave its audiences too disgusted to stay in the theater, between the depictions of obesity and unsanitary food-production conditions. Instead, director Richard Linklater opted for a sprawling, multi-character, Robert Altman-inspired depiction of the web of connections behind each “Do you want fries with that?” This spans from the top, where the marketing director (Greg Kinnear) of a McDonald’s-like chain investigates possible contamination, down to the illegal immigrants who make up the chain’s work force. The film has its share of shocking moments, including an inevitable trip to the slaughterhouse, but it’s more memorable for its depiction of the effects of corporate homogenization on the fictional Colorado town at its center, where residents eat what’s available without much thinking about where their food comes from, where their money goes, or what the consequences of it all might be.
5. Lolita (1962) “How did they ever make a movie of Lolita?” asked the tagline for Stanley Kubrick’s scandalous 1962 adaptation of Lolita, echoing the concerns of anyone who’d ever read Vladimir Nabokov’s controversial novel, or even heard it spoken about in hushed whispers. It wasn’t just the taboo content—a sordid sexual affair between pedophile intellectual Humbert Humbert and a sexually precocious 12-year-old named Dolores Haze after her mother’s death—that made the book seemingly impossible to legally adapt for film in the early ’60s. It was also the book’s tricky, innately literary tone and structure: Much of Lolita’s enduring appeal is rooted in the brutally witty literary voice of the self-serving, patently unreliable narrator, a bitchily brilliant teacher and writer fond of multi-lingual puns, and convinced he’s a victim of fate, not a monstrous child molester. That didn’t stop Stanley Kubrick from attempting the impossible with a film adaptation that stressed the pitch-black comedy at the book’s nasty core while understandably downplaying its forbidden sexuality and underlying romanticism. Kubrick’s Lolita is a different beast than the book that inspired it. Kubrick dramatically expanded the role of Humbert’s arch-nemesis Clare Quilty (largely to provide a rich showcase for the chameleon-like Peter Sellers), changed the chronology of events by beginning with the ending of the book, and made the title nymphet much more an adult than in the novel. But his film is nevertheless brilliant, deeply sad, and graced with some remarkable performances—most notably, James Mason as Humbert Humbert, Sellers as Quilty, and Shelley Winters as Dolores’ self-deluded mother—in spite of the restrictions under which Kubrick worked. Kubrick’s achievement is even more remarkable when compared to Adrian Lyne’s more sexually explicit, dopily maudlin 1997 adaptation.
6. Orlando (1992) Virginia Woolf’s 1928 novel Orlando: A Biography isn’t as dependent on the stream-of-consciousness prose that makes her other books so difficult to adapt, but that doesn’t make an easy project out of Woolf’s centuries-spanning tale of an undying young man who becomes a woman about a century into his life. Writer/director Sally Potter took a lot of liberties with Woolf’s plot, but her adaptation offers a thematically similar tour of several centuries of British history, and how the roles of women and men have changed over the years. It’s visually gorgeous and anchored by a star-making performance from Tilda Swinton, who’s convincing and sexy on both sides of the gender divide. Bonus sexually ambiguous points: Memoirist and queer icon Quentin Crisp does a neat turn as Queen Elizabeth.
7. American Psycho (2000) There are those who regard Bret Easton Ellis’ 1991 novel as a modern classic of ferocious, deadpan satire, and those who adhere to the general view that greeted its original publication: that it’s an affectless hash of brand names, record reviews, and torture-porn. Either way, its dulled-out first-person narration, combined with the extreme violent and sexual content, made it seem like a non-starter as a movie property. Then director Mary Harron and screenwriter Guinevere Turner made the material their own by turning it into a period piece set in the mid-1980s. With a central performance by Christian Bale that wraps an atomic core of pulsating rage inside a sleek, polished yuppie surface, this icy black comedy apotheosizes Ellis’ splatter satire of careerist consumerism, even as it folds the book itself in as one of its targets.
8. “The Dead” (1987) Over the course of his career, John Huston earned a reputation as a specialist in movies based on “classic literature,” but most of his triumphs came from a certain kind of literature: Whether it was the hard-boiled detective fiction of Dashiell Hammett (The Maltese Falcon), the war stories of Stephen Crane (The Red Badge Of Courage), or Rudyard Kipling’s boy’s-adventure yarns (The Man Who Would Be King), they were simple stories long on action and colorful language, ready for exploitation by good actors. For his last film, though, Huston stretched himself by taking on the final story in James Joyce’s debut collection, Dubliners. It’s a small story, mostly set at an Epiphany party in a few crowded rooms, with a final meditation set inside the hero’s head. But Huston, working with an expert cast headed by Donal McCann and Huston’s own daughter Anjelica Huston, staged the party scenes so they feel as big as life itself. Then, having shown what he could do with the framework of Joyce’s characters and dialogue, he backs off and conveys the hero’s epiphany by having McCann read the passage over images of winter landscapes. Part of knowing how to adapt the unadaptable is knowing when to let the original author tow you to the finish line.
9. Everything You Always Wanted To Know About Sex* (*But Were Afraid To Ask) (1972) Studios have been known to buy the rights to bestselling books that are unimaginable as films just for the bragging rights, which may be how someone ended up with the rights to Dr. David Reuben’s blockbuster sex manual, written as a series of short answers to questions about sexual matters. Fortunately, Reuben had unknowingly made an enemy of Woody Allen, who saw Reuben plugging his book on The Tonight Show by recycling Allen’s old standup act without attribution. (Johnny Carson: “Is sex dirty?” Reuben: “Only if you’re doing it right.”) Appalled by Reuben’s slick, media-friendly glibness and his dopey book, Allen wrote and directed a movie consisting of seven vignettes that stretch the premises of questions from Reuben’s book as far as they can go. As with most sketch-based movies, the film is uneven—the sight of Lou Jacobi in drag never did anybody any good—but the best segments remain high points of Allen’s early period, including Gene Wilder’s performance as a successful Manhattan doctor destroyed by his passionate affair with a sheep, and the concluding episode, “What Happens During Ejaculation?” featuring Allen as a sperm cell anxious that he’ll “end up on the ceiling.” (An eighth segment, starring Allen as a spider and his ex-wife Louise Lasser as a black widow who mates with him, then kills and consumes him, was filmed but deleted from the finished movie. The title: “What Makes A Man A Homosexual?”)
10. The Lord Of The Rings trilogy (2001-2003) J.R.R. Tolkien himself thought nobody could turn his fantasy epic into a dramatic adaptation that audiences could take seriously, and he might have been right—that is, if special effects hadn’t developed to the point they had by the turn of the century, if there hadn’t been backers willing to foot the bill for a series of epic-length films determined to get the details right on the scale they demanded, and if Peter Jackson and his co-adapters hadn’t been ruthless enough with the material to dump characters like Tom Bombadil overboard. Many other attempts to adapt Tolkien into film and other media suffered from being too faithful, in ways that weren’t essential to the story or spirit of the books, but that did eat up that most precious resource to makers of would-be epics: time. Jackson, coming from a background in horror and fantasy movies, was able to apply what he learned from the cinema of Ray Harryhausen, Merian C. Cooper, and Run Run Shaw to create a massive piece of entertainment that’s both true to the books and a celebration of the pleasures of sword fights and CGI gruesomeness.
11. Mean Girls (2004) Rosalind Wiseman’s 2002 book Queen Bees And Wannabes: Helping Your Daughter Survive Cliques, Gossip, Boyfriends, And Other Realities Of Adolescence caused a stir when it revealed what many young women already knew: Adolescent girls are often the worst, especially toward each other. Half an examination of “girl world,” half an advice book for parents at their wits’ end about what to do with their miserable/unbearable spawn, Wiseman based her nonfiction book on years of research in the field listening to girls discussing how cliques affected their lives. Due to a lack of ongoing narrative, Wiseman’s book didn’t seem like an obvious choice for movie adaptation, but screenwriter Tina Fey not only based 2004’s Mean Girls on the topic of high-school backbiting and hierarchy, but also used Wiseman’s investigative style when introducing Lindsay Lohan’s character Cady, who observes North Shore High as if she were a zoologist examining a new habitat.
12. Brief Interviews With Hideous Men (2009) Like all David Foster Wallace’s work, his 1999 short-story collection Brief Interviews With Hideous Men was deemed unadaptable primarily because of his distinctive hyper-articulate and extensive dialogue, which would balloon to untenable length if filmed without significant alterations. Also, it’s a collection without an obvious overall narrative, which seemed to preclude a movie version. During a staged reading in college of the book’s recurring centerpiece segments—men’s misogynist monologues, articulate confessions, and reminiscences of their dads, delivered in response to an unknown interviewer only represented by a recurring “Q”—John Krasinski thought the cumulative emotional effect created a narrative backbone. His solution to the lack of plot was to fill out “Q” as graduate student Sara Quinn (Julianne Nicholson), whom Krasinski claims Wallace blessed over the phone as exactly how he’d conceived of this unknown interrogator. The movie is hit-and-miss: Some of the monologues flounder badly, but others (like Bobby Cannavale’s one-armed pickup artist) knock it out of the park.
13. Moneyball (2011) While Michael Lewis’ 2003 book Moneyball: The Art Of Winning An Unfair Game has been hailed as an insightful look into how Oakland’s Billy Beane revolutionized the way a small-market baseball team could compete with richer organizations, it hardly comes off as an adaptable tome. Unlike Lewis’ other book about statistical analysis in sports, The Blind Side, there’s no easily teased-out narrative thread. And while such an underdog tale would have great appeal, the book’s detailed discussion of sabermetrics—a specialized technique of analyzing statistics—is dense enough to make even the most ardent baseball fan yawn. Yet Steven Zaillian and Aaron Sorkin’s screenplay builds a narrative construct that hews close to the actual story while using creative license to flesh out Beane (Brad Pitt) and his story, which stands at the center of that narrative. Strong acting turns from Pitt, Jonah Hill (as composite character Peter Brand), and Philip Seymour Hoffman (as A’s manager Art Howe) help spark the central conflicts and create the necessary tension to make Bennett Miller’s deftly directed film come to life.
14. Crash (1996) The J.G. Ballard novel Crash concerns itself with the obscure, peculiar fetish symphorophilia, which associates watching or staging accidents with sexual arousal. Naming a narrator after himself, Ballard takes a voyeuristic journey into a subculture of former car-accident victims who have come to confuse and intermingle the sensation of crashes and sexual pleasure. It’s a deadly pursuit: Its members stage collisions, and its deranged leader imagines an ecstatic death in a head-on crash with Elizabeth Taylor. Ballard realizes it with appropriately obsessive detail, to the point where the abstractions of the prose dominate the spare remnants of the plot. Material this singularly odd and disturbing generally isn’t in danger of being adapted into a movie—lest it be slapped with the NC-17 it was slapped with—but director David Cronenberg proved ideal for the task, turning it into another of his ongoing series of films about the horrors of the psyche manifesting themselves on the body. Naturally, it polarized critics and audiences sharply—it won a Special Jury Prize at Cannes over the fervent objection of jury president Francis Ford Coppola—but unlike the 2004 Best Picture winner, it’s a Crash that stands the test of time.
15. Time Regained (1999) How do you go about adapting Marcel Proust’s novel Remembrance Of Things Past, a seven-volume, time-jumping, 1.5-million-word behemoth about the nature of memory? For the late Raúl Ruiz, a Chilean director working with the abundant resources of the French film industry, step one was to lose the first six volumes. In two and a half hours, Ruiz designed his movie as a companion to the seventh volume rather than a fully comprehensible work in its own right, which favors Proustian scholars more than the uninitiated. Still, Ruiz and co-writer Gilles Taurand boldly attempt to translate Proust’s narrative digressions into formal flights of fancy. Rather than straighten out the timeline, the film takes off from a single spark of memory—like the bite from the famous madeleine that brings the past rushing to the fore—and turns those moments out of time into dizzying narrative pirouettes.
16. Where The Wild Things Are (2009) From the moment it was announced that director Spike Jonze and screenwriter Dave Eggers were adapting Maurice Sendak’s Where The Wild Things Are into a film, the Internet bubbled with contempt, wondering how it was possible to expand a 10-sentence picture book into a 100-minute movie without losing its essential emotional directness and simplicity. Turned out that Jonze and Eggers didn’t entirely need to: The film adaptation is richer and more complicated than the book, with more of a sense of the life of angry, frustrated 9-year-old protagonist Max. Eggers and Jonze spend the extra time letting the audience feel Max’s emotions, as expressed through interactions with the “wild things” that represent different parts of his psyche. It’s an adaptation that thoroughly respects its inspiration, both in the gorgeous visuals, taken from Sendak’s art, and in its storyline, but also in its expression of the storms, rages, confusions, and sudden coolings-off of childhood. And yet it isn’t a slavish adaptation; it’s one that draws out the ideas of a simple book for children, and turns it into a tender adult reminder about what childhood was like.
17. Johnny Got His Gun (1971) Statistically speaking, it’s a fair bet that more people know Johnny Got His Gun from the film clips incorporated into the video for Metallica’s “One” than have ever actually seen the film, let alone read Dalton Trumbo’s original 1938 novel. Although it only took two years to inspire a radio adaptation of the book (starring James Cagney, no less), another 31 years passed before it transitioned from printed page to silver screen, and even then only because Trumbo wrote and directed the film himself. The challenge: How to visually represent a novel about a World War I soldier who wakes up in a hospital bed to discover that, although his mind is in perfect working order, he’s now a deaf, blind quadruple amputee without teeth or tongue. Using his advantage as the author of the original source material, Trumbo’s cinematic take on the story of Joe Bonham—played in the film by Timothy Bottoms, with the character’s thoughts and memories presented via flashbacks and fantasy sequences—proved so creatively successful that it won the Special Jury Prize at the 1971 Cannes Film Festival.
Don’t miss our sister list, Why did they ever make a movie of…?: 15 unsuccessful adaptations of “unadaptable” books´