1. From Hell (2001)

There are plenty of reasons to consider a book unadaptable for the big screen: Too long, too niche-y, too divisive, too internal, difficult content, and so on. Successful adaptations generally find unique, innovative ways of tackling difficult material. Unsuccessful ones, on the other hand, often just throw out everything idiosyncratic or complicated and sandwich a few of the book’s signifiers into a more familiar plot and structure. For instance, Alan Moore and Eddie Campbell’s From Hell, a 550-page-plus graphic novel exploring the Jack The Ripper murders in depth, is impossible to summarize neatly. [Spoilers ahead.] Moore lays out the theory that royal physician William Gull performed the killings to silence a group of women attempting to blackmail the crown with information about an illegitimate royal baby. But he also stretches into an occult history of London landmarks, a series of psychic visions, and a vast network of mystical ideas about Victorian society and the past and future, covering everything from attempts to quash feminism via ritual sacrifice to the conception of Adolf Hitler. The book is a gigantic bird’s-nest of heady concepts, many of them laid out in vast, research-augmented detail by a character who’s demonstrably insane—and by an author who styles himself as insane. The Hughes brothers dumped virtually all of this content for their adaptation, turning the story into a frustratingly familiar murder mystery being solved by psychic detective Johnny Depp. For a little extra touch of conventionality, Depp naturally falls in love with the Ripper’s final victim-to-be, Mary Kelly (played by Heather Graham).

2. Slapstick (Of Another Kind) (1982)

The tricky tragicomic tone Kurt Vonnegut mastered has proven hellishly difficult to recapture cinematically. In print, Vonnegut’s 1976 novel Slapstick, which he described as “the closest I will ever come to writing an autobiography,” is a surreal, absurdist science-fiction tragedy about deformed twins who together form a genius intellect, but pretend to be mentally challenged. Vonnegut uses that story to poignantly explore the nature of partnerships and love. None of that translates to the awful 1982 adaptation of the film, however. The miscalculations begin with changing the twins into space aliens, and extend to casting a long-in-the-tooth Jerry Lewis in a hammy dual role as one of the twins (Madeline Kahn is wasted as the other) and the twin’s ostensible earth “father,” regarded as the most beautiful man on earth. Slapstick (Of Another Kind) reduces the personal, delicate combination of comedy and tragedy at the novel’s core into a grotesque, broad comedy that’s an embarrassing vehicle for Lewis at his most over-the-top. This may be the single worst Vonnegut adaptation in film, and considering how badly filmmakers have botched other adaptations, that’s saying an awful lot. And speaking of Vonnegut…

3. Breakfast Of Champions (1999)

Vonnegut’s 1973 novel Breakfast Of Champions is a metafictional jamboree populated with characters from his other books and decorated with his own drawings, written in the hope that it would help him “clear my head of all the junk in there.” Alan Rudolph, a gifted, one-of-a-kind filmmaker who didn’t need an excuse to overdose on his taste for fanciful imagery and overblown whimsy, tried to adapt the book by putting all the junk up on the screen, replacing Vonnegut’s gentle shrug with a sledgehammer touch. Dwayne Hoover (Bruce Willis), the symbolic representative of what used to be called Middle America, makes his entrance hiding in the bathroom with a gun in his mouth, trying to work up the nerve to pull the trigger—and that’s the least hysterical he or the movie ever get. Recognizing the project as a labor of love, Vonnegut agreed to appear in a cameo as a commercial director, which didn’t stop him from later offering his opinion that the movie is “painful to watch.”

4. Bartleby (2001)

Herman Melville’s 1853 novella “Bartleby, The Scrivener: A Story Of Wall Street” depicts the breakdown of a lowly Wall Street employee who slowly starts refusing to perform his duties, responding with an unchanging phrase: “I would prefer not to.” It’s a rich, mysterious piece that’s lent itself to many different interpretations over the years, some focusing on Bartleby’s psyche, and others on its commentary on capitalism. As to what director Jonathan Parker was up to with his adaptation, Bartleby, who knows? Parker updates the action to a garishly decorated modern office and lets Crispin Glover chew the scenery on his way to a meltdown interrupted by some wacky office antics, some of which involve Joe Piscopo.

5. Mrs. Dalloway (1997)

Virginia Woolf’s landmark 1925 novel is set almost entirely inside the heads of its two main characters—Clarissa Dalloway, the respectable London wife preparing for her big party, and the shattered World War I veteran Septimus Smith—as they make it through a single June day, experiencing thoughts and memories more complex and troubling than anyone looking at them could guess. The movie, directed by Marleen Gorris and adapted by Eileen Atkins, makes the point of how isolated the characters are from the world around them all too well, by applying a conventional Masterpiece Theater approach instead of finding a cinematic equivalent to Woolf’s interior monologues. The actors just walk through their paces, sometimes with their thoughts recited in voiceover; as the movie goes on and the thoughts become darker and more essential, the chunks of voiceover just get longer and longer. Vanessa Redgrave is so good in the title role that much of the movie works anyway when she’s onscreen, but Septimus’ anguish over his estrangement from his own life is almost inseparable from Rupert Graves’ apparent distress over not knowing what’s expected of him.

6. Wanted (2008)

Some might consider Mark Millar and J.G. Jones’ limited-run comics series Wanted unadaptable just for the graphic content: The plot centers on a sad loser who learns his father was a supervillain assassin, and that he, too can develop powers by self-actualizing himself via wholesale rape and murder. In particular, his initiation into a brotherhood of supervillains involves killing anyone who ever annoyed him or hurt his feelings—for instance, “the chick who said no when I asked her to a movie.” It’s a petty, sophomoric rage fantasy that wallows in pointless depravity and nihilism, and ends with the protagonist breaking the fourth wall to tell the reader, “This is my face whilst I’m fucking you in the ass.” But on top of all that, Wanted is also narrowly aimed at a niche-y audience of comics fans who get comics-history visual jokes and can swallow the high-concept plot, which involves supervillains manipulating their universe to retroactively eliminate superheroes. It’s no surprise that none of this made it into the dull, generic 2008 film adaptation, which hung onto the idea of a secret society of assassins embracing the son of a former member, and ditched nearly everything else about the story. Instead of supervillains retroactively recreating the universe in their own image, the movie has “good” assassins who only kill evil folk, thanks to a magical loom that tells them what to do. It’s hard to say which version of this story is more ridiculous.

7. Ulysses (1967)

James Joyce’s Ulysses has mostly proven a boon to theatrical producers, who tend to isolate smallish chunks of the massive work to give actors the chance to revel in the richness of the language. However, an ambitious film adaptation was directed, produced, and co-written by Joseph Strick, who was part of what passed for the American independent film movement in the 1950s and ’60s. His version of Ulysses was congratulated for being “faithful” to its source, which translates to taking all the scenes and dialogue directly from the novel and staging them unimaginatively, without capturing any of the novel’s spirit, humor, energy, imagination, or sensuousness. (Another Ulysses film adaptation, 2003’s Bloom, reportedly attempts to find a cinematic style appropriate to the material, but it’s never been released in the United States.) The movie did get an Academy Award nomination for best adapted screenplay, and Strick’s subsequent movie versions of Joyce’s A Portrait Of The Artist As A Young Man and Henry Miller’s Tropic Of Cancer just go to show that you shouldn’t encourage some people.


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8. Watchmen (2009)

Alan Moore and Dave Gibbons’ landmark graphic novel almost made it to the screen several times before Zack Snyder took a crack at it, taking a sprawling, largely faithful approach to the material. Trouble is, that faithfulness reveals how tough it is to squeeze Moore’s sprawling, multi-threaded story into feature length: It gets most of the details right, but never creates a convincing big picture from them. Then there are the changes and additions that don’t quite sit right, from the new ending to the butt-obvious songs on the soundtrack. Oddly enough, the one scene in which Snyder takes great liberties—an opening-credits sequence that moves the action across several decades—finds a dynamism that the rest of the film lacks. It isn’t a terrible movie, and maybe the best one that could be hoped for from such a straightforward take on the material. But maybe straying wasn’t such a bad idea.

9. Lord Of The Rings (1978)

One reason to be grateful for the cinematic-franchise glut of the past decade or so: It made a movie adaptation of J.R.R. Tolkien’s fantasy trilogy possible. Before the days when a popular genre film guaranteed a sequel (or sequels), any director or screenwriter looking to bring The Fellowship Of The Ring, The Two Towers, and Return Of The King to the big screen did so with an eye toward compressing as much of the books’ epic scope as possible. Hence Ralph Bakshi’s 1978 animated disaster, The Lord Of The Rings, a misbegotten, clumsy attempt to cram a little more than half of the original story into 133 minutes. Using a rotoscoping technique that fails to cover the community-theater physical performances and goofy costume design (the fearsome Balrog of Moria appears to be wearing bunny slippers), Bakshi’s version is a sloppy, jerky mess, by turns tedious, baffling, and campy, full of bad acting, weird character models, and unfunny attempts at humor. Combined with the narrative’s abrupt conclusion, in which none of the main plot is resolved and no sequels are promised, the film is a fine example of how source material can defeat an artist who isn’t up to the task. Rankin-Bass tried to tie up loose ends with 1980’s Return Of The King, but since that film was done more in the style of the studio’s early Tolkien adaptation, The Hobbit, full of irritatingly catchy songs (“Frodo Of The Nine Fingers,” “Where There’s A Whip, There’s A Way,” etc.), and kid-friendly animation, it came off less as a triumphant finale, and more like a dispatch from an alternate reality where fantasy fans never aged past 9.

10-11. He’s Just Not That Into You (2009)/I Hope They Serve Beer In Hell (2009)

There’s a special shelf in cinematic hell for ultra-generic fiction movies based on ultra-specific non-fiction books. But then, it’s hard to know how to adapt a self-help book like He’s Just Not That Into You: Your Daily Wake-Up Call into a film, given that it’s largely dishy relationship advice. And Tucker Max’s infamously smug, self-serving collection of frat-brat adventures, I Hope They Serve Beer In Hell, lacks any kind of through-line or narrative, unless it’s “Tucker Max gets some, because he’s awesome, at least as he tells it.” But both books were bestsellers, and studio flacks love familiar properties almost as much as they love familiar stars. So both books wound up loaning their names to films that vaguely embodied their themes, but only a tiny sliver of their actual content. And ultimately, both adaptations undermined the books’ intentions. Where He’s Just Not That Into You the book offered women practical advice in recognizing and giving up on a disinterested crush object, the perky, sprawling romantic-comedy adaptation promises that true love awaits around every corner for the patient, determined woman who’s willing to make an idiot out of herself. And where Max’s I Hope They Serve Beer is about an unrepentant ass who loves his life, the movie version has the Max stand-in realizing that he’s a shithead and mending his ways, after a bunch of dispiriting sexcapades focusing more on his friends than on him. It’s almost as though the people behind the films didn’t even read the books… naaaaah. Not possible.

12. Atlas Shrugged (2011)

Atlas Shrugged presents an endless series of obstacles to cinematic adaptation. It is, first and foremost, a vehicle to spread the toxic “philosophy” of Objectivism, and it’s so relentlessly didactic and talky that at one point, mysterious hero John Galt delivers a speech that, depending on the printing, runs 60 to 70 pages. If that weren’t prohibitively intimidating enough, the book tops 1,000 pages and concerns a future where trains, of all things, form the center of the global economy. Yet that hasn’t stopped heroically self-interested filmmakers from trying to bring it to the big screen. In 2011, journeyman actor Paul Johansson finally succeeded in directing a long-threatened film adaptation, but it proved a Pyrrhic victory at best. Taylor Schilling leaves a terrible charisma void in the crucial lead role of a railroad magnate out to save humanity from the evils of collectivism with the help of a miraculous new alloy, and the plot proves even more ridiculous and anachronistic on film than it does in print. The film flagrantly defies the old dictum to show rather than tell, and it was rightly and widely mocked by critics and ignored by audiences. It appears you can’t keep a bad idea down, however: In blatant defiance of the wisdom of the all-knowing free market, plans have proceeded for a second installment in the series, despite the unmistakable failure of the first film.

13. Jonathan Livingston Seagull (1973)

Richard Bach’s 127-page “fable” about a seagull who’s ostracized by his own flock for daring to dream of bigger things became one of the great, inexplicable blockbuster publishing successes of the early ’70s, the kind of book people pass off on other suckers and read passages from at their weddings. If the book hadn’t had that effect on its fans, it probably never would have been considered for the basis of a live-action movie in the pre-CGI era, considering that its only characters are birds. But when producer-director Hall Bartlett—perhaps best remembered today for Zero Hour!, the movie that inspired the spoof Airplane!—received a copy of the book, he felt he had been entrusted with a holy mission to bring Richard Bach’s inspirational wisdom to the screen. Bartlett plowed his savings into the film, which comprises two full hours of footage of birds and special-effects gliders that are supposed to look like birds, accompanied by the sound of actors (James Franciscus, Hal Holbrook, Richard Crenna, Dorothy McGuire) reading the birds’ lines on the soundtrack. The only person who came out of the project with his bank account (though not his reputation) enhanced was Neil Diamond, who had a huge hit with the soundtrack album.

14. Portnoy’s Complaint (1972)

Philip Roth’s breakthrough bestseller is a white-hot comic monologue delivered by the hero from his analyst’s couch. Liberated from the polite constraints of his earlier fiction (most of which was polite only by comparison), Roth indulged himself in wild slapstick sex scenes, outrageous fantasies, and over-the-top ethnic caricatures. None of this material was crying out to be realized onscreen by flesh-and-blood actors, but it would have helped if the movie had been made by someone who understood the material. Instead, the movie was directed, produced, and adapted by the writer Ernest Lehman, best known for his screenwriting assignments for Alfred Hitchcock. He had never directed a movie before or after, and a pretty good case could be made that he didn’t direct one when he was on the set for this thing, either. Lehman didn’t know how to stylize the fantasy sequences or guide the actors trapped in them, so Lee Grant and Jack Somack, as the hero’s parents, look exposed and embarrassed. Trying to deliver what’s wanted of them, they give helplessly strident performances in cartoon roles. Roth’s scalding humor is subsequently diluted into something so coarse and corny that the ugly-looking, amateurishly staged movie is like an R-rated sitcom. Not a good sitcom, either.

15. Under The Volcano (1984)

Malcolm Lowry’s 1947 novel recounts the last day in the life of Geoffrey Firmin, a proudly alcoholic British expatriate living in a small Mexican town and self-destructing during the celebrations for the Day Of The Dead. Under The Volcano is written in an electric, hallucinatory style meant to convey its hero’s self-loathing and existential sickness, and even though its language is far more important than most of what accounts for action in the book, it attracted a great many directors, including Luis Buñuel and Sam Peckinpah, who hoped to adapt it to the movies, some of them working at it for years before deciding that the job was (in Buñuel’s words) “impossible.” The movie that finally did get made, directed by John Huston from a script by Guy Gallo, was well-received by many critics at the time, and earned Albert Finney an Academy Award nomination, but it tends to confirm the early opinion that the book was unfilmable. A more daring, unpredictable style is necessary to give viewers a taste of what Firmin sees and feels, the way Lowry’s prose did, and too much of Huston’s movie amounts to watching Finney project to the rafters in a picture-postcard landscape.

And don’t miss yesterday’s sister list, of 17 successful adaptations of “unadaptable” books.