1. 100 Years of Solitude by Gabriel García Márquez
Why it's so hard to adapt: The plot concerns seven generations of the Buendía family, which is a lot of terrain to cover. Character names are repeated over and over again. Some readers consult a family tree, but that would be tougher to reference while watching the film in a theater.
Has anyone tried: Not really. García Márquez has not sold the rights to his book, perhaps realizing no one could do it justice. The 1984 Japanese film Farewell to the Ark is a very loose (and not officially sanctioned) adaptation.
2. House of Leaves by Mark Z. Danielewski
Why it's so hard to adapt: Footnotes within footnotes. The experience of reading the complicated novel is intentionally confusing and claustrophobic to mirror the subject matter. There are also multiple unreliable narrators, which make reading the book a fun challenge — but watching a film version unbearable.
Has anyone tried: Nope. Danielewski won't sell the rights, thankfully.
3. Griffin & Sabine: An Extraordinary Correspondence by Nick Bantock
Why it's so hard to adapt: It's an epistolary novel — and not only that, it's one in which the letters and postcards are largely removable. Reading it is an interactive and tactile experience, with the memorable artwork often doing as much work as the text.
Has anyone tried: It's happening! Renegade Films has bought the rights and will be bringing Bantock's story to screen. In a press release, the author said, "This is the first time I've felt comfortable that the essence of the story is understood. Transitioning this tale from a novel to a movie will test the bounds of dreams and creativity, providing an opportunity to create something intelligent, entertaining and visually extraordinary."
4. Ulysses by James Joyce
Why it's so hard to adapt: The so-called best English-language novel of the 20th century takes place on a single day with a stream of consciousness style that has confounded readers since its publication in 1922. It's a modern retelling of The Odyssey where nothing really happens — or does it? (I don't know.)
Has anyone tried: Yes, twice. The 1967 film Ulysses is very faithful to the novel and even won an Academy Award for Best Adapted Screenplay. More recently, the 2003 film Bloom attempted to recapture the stream of consciousness technique visually.
5. Paradise Lost by John Milton
Why it's so hard to adapt: Well, the characters include God, Satan, Adam, and Eve, and those are big shoes to fill. It's not that people haven't attempted Biblical adaptations before — it's that Paradise Lost is more about Milton's poetry than the story, which everyone already knows.
6. The Dark Tower series by Stephen King
Why it's so hard to adapt: Stephen King's epic fantasy series takes place in different worlds — some very close to our own (with minor differences) and others completely foreign to us. It has characters from other Stephen King novels, and even — spoiler alert — Stephen King himself. Yes, things get very, very meta.
Has anyone tried: Yes, but to no avail so far. First it was J.J. Abrams, then it was Ron Howard. The project has bounced around from Universal to HBO to Warner Bros., and as it stands, nothing has actually been filmed.
7. Woodcutters by Thomas Bernhard
Why it's so hard to adapt: The entire novel takes place from the narrator's perspective as he attends an elegant dinner party and passes judgment on everyone there. For the most part, he is sitting by himself in a chair with a glass of champagne, thinking. Not exactly thrilling to watch.
Has anyone tried: Nope.
8. As I Lay Dying by William Faulkner
Why it's so hard to adapt: There are 15 different narrators, some of whom have a much harder time expressing themselves than others. It's a fairly straightforward story of one family trying to bury their mother, but it's incredibly difficult to follow, with every chapter shifting perspective.
Has anyone tried: James Franco just did it. He co-wrote the film adaptation and stars as Darl Bundren. As for whether it's a successful adaptation, that's up to the viewer. But reviews thus far have been largely negative.
9. To the Lighthouse by Virginia Woolf
Why it's so hard to adapt: There isn't much of a plot, because the novel is mostly about the characters' interior thoughts. Any substantial dialogue would have to be invented by the adaptation's screenwriter, as there is very little in the book.
Has anyone tried: Yes, there was a made-for-TV movie in 1983.
10. The Mezzanine by Nicholson Baker
Why it's so hard to adapt: The entire novel takes place on an escalator. On an escalator! It's all about what goes through the narrator's head, and while that is an interesting idea for a book, it makes zero sense as a movie. Also, there are a whole lot of footnotes, including a lengthy final footnote on the footnotes themselves.
Has anyone tried: Thankfully, no.
11. The Basic Eight by Daniel Handler
Why it's so hard to adapt: It's a satire on what students learn in high school English classes, and while that's very funny, it works best on the page. For example, Handler labels all foreshadowing as foreshadowing. There are also study questions and standardized testing exams. That just wouldn't play as well onscreen.
Has anyone tried: It was rumored to have been optioned, but there's nothing currently in the works.
12. At the Mountains of Madness by H.P. Lovecraft
Why it's so hard to adapt: Ask Guillermo del Toro. It's not your typical horror novella — just the plot description will have most readers confused. The concepts, while very familiar to Lovecraft fans, require a great deal of explanation — not to mention some pretty incredible special effects, should the Elder Things be realized onscreen.
Has anyone tried: Guillermo del Toro's struggles with the Lovecraft story have been well documented. Despite numerous attempts, he has not been able to get the project off the ground, whether due to studio intervention, budgetary concerns, or the fact that Prometheus covered very similar ground.
13. The Sandman series by Neil Gaiman
Why it's so hard to adapt: It's a 75-issue comic book series, which doesn't translate easily to film. The characters and themes are complex, with endless references to other mythologies. And the story shifts over time, eventually becoming a fantasy series with a tragic hero at its center.
Has anyone tried: Oh, sure. But as Neil Gaiman put it in 2007, "I'd rather see no Sandman movie made than a bad Sandman movie." Past attempts through the '90s have been weak, according to those who read the scripts. In 2010, there was a Sandman series in development, but that has since been scrapped.
14. Atlas Shrugged by Ayn Rand
Why it's so hard to adapt: While ostensibly a novel, this is really Ayn Rand's allegorical treatise on objectivism. The story serves the larger goal of the message she's trying to convey. It's also really long, including a 70-page speech that wouldn't play so well onscreen.
Has anyone tried: Remarkably, yes. The book was split up into three parts by filmmakers. The first two films bombed, and now Kickstarter is funding the third. So much for objectivism.
15. Infinite Jest by David Foster Wallace
Why it's so hard to adapt: It's over 1,000 pages long. The plot is freewheeling, with countless characters. And oh, yes, there are endnotes: 388 of them in total, and some of those endnotes have footnotes of their own.
Has anyone tried: No, although the book was heavily referenced on an episode of Parks and Recreation. So there's that.
16. Alphabetical Africa by Walter Abish
Why it's so hard to adapt: It's not a novel so much as a "constrained writing experiment." Each chapter presents a new letter, in alphabetical order, and Abish can only start words with letters that have been introduced in previous chapters. That means the first chapter is only words beginning with "A," and the second chapter has "A" and "B" words. Crazy, right?
Has anyone tried: No one has had the gall.
17. Pale Fire by Vladimir Nabokov
Why it's so hard to adapt: The novel is a 999-line poem by fictional poet John Shade, with notes and commentary by fictional editor Charles Kinbote. Readers can decide to read the poem straight and then read the notes, or to read them both concurrently, as the notes reveal the plot piece by piece. It's dense either way.
Has anyone tried: No.
18. The Wheel of Time series by Robert Jordan
Why it's so hard to adapt: The epic fantasy series was originally planned to be six books long — and then it got expanded to 14. Length aside, there's just a lot going on, including references to numerous different mythologies. Readers often consult the official companion book for assistance.
Has anyone tried: Yes, but with no success. NBC was going to do a miniseries based on The Eye of the World, but that fell through. And while Universal allegedly optioned the rights to the series in 2008, nothing has been made.
19. Maus by Art Spiegelman
Why it's so hard to adapt: Holocaust stories are frequently translated to film — they're hard to watch, not necessarily to make. But Maus is an interesting case, because the graphic novel uses animals as stand-ins for humans. Any film would have to be animated, and animated mice and cats don't really have the right connotation for such heavy subject matter.
Has anyone tried: Not really, though there's been talk. Art Spiegelman has said that despite offers, he's reluctant to turn his work into a film, as there would be too many people involved with the production.
20. The Road by Cormac McCarthy
Why it's so hard to adapt: The post-apocalyptic novel has sparse dialogue, instead focusing on the lyrical narration. There is little information about what caused the end of the world, and the characters aren't even given names, which makes the story more of a modern fable than anything else.
Has anyone tried: Yep. The film adaptation of The Road was released in 2009, starring Viggo Mortensen and Kodi Smit-McPhee. It actually got pretty good reviews.