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You know when you read a book and it seems like it’s confusing for the sake of being confusing or *impressive*? (We don’t want to name names, but one example that comes to mind rhymes with Shmavity’s Shmainbow.) It’s kind of frustrating. That’s not the case with the following eight titles, which are difficult to read, but more than worth your time and effort. 

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hardest books ever cortazar
Cover: Pantheon Modern Writers Series; Background: Twenty20

Hopscotch by Julio Cortazar

Magical realism isn’t an easy genre, but Hopscotch (Rayuela in its original Spanish) has to be one of its most difficult examples. Cortázar’s 1963 novel about Paris bohemians isn’t content to confuse readers with just a stream-of-consciousness narrative. It can actually be read in two completely different ways: from front to back, or by “hopscotching” through the 155 chapters following a "Table of Instructions" from the author. Oh yeah, and did we mention there are designated “expendable” chapters that don’t need to be read to understand the plot? All that said, you’ll feel a tremendous sense of accomplishment upon finishing it—no matter how you get to the end.

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hardest books ever wallace
Cover: Back Bay Books; Background: Twenty20

Infinite Jest by David Foster Wallace

Confession: It took us three tries to finish Wallace’s 1996 masterpiece, and it was totally worth it. The sprawling, 1,079-page tome covers everything from addiction and tennis to film theory and Quebec separatism. Sad, funny, thought-provoking and shockingly inventive, there’s a reason it’s held in such high esteem.

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hardest books ever faulkner
Cover: Random House; Background: Twenty20

Absalom, Absalom! by William Faulkner

Long, winding sentences were a trademark of Faulkner’s, and there’s no greater example of this than Absalom, Absalom! (which was awarded, in 1986, the Guinness World Record for “longest sentence in literature,” clocking in at 1,288 words). This 1936 novel is about, very generally, Thomas Sutpen, a Southern man born into poverty who finds wealth, marries up and causes his own demise. Told from multiple perspectives in a sometimes stream-of-consciousness style, it’s—to say the least—confusing. As one Goodreads user puts it, the novel is, “at first, like walking into your friends having an important conversation but, because you missed the first half of it, you can’t tell whom it’s about and why they sound so absorbed by it.” Still, it’s considered by critics to be Faulkner’s finest work (and we liked it a whole lot more than As I Lay Dying).

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hardest books ever martin
Cover: Bantam; Background: Twenty20

A Game of Thrones by George R.R. Martin

You think the show is confusing? Try the books, where you don’t have the added gift of being able to distinguish characters from one another based on their looks. Martin’s series is a ridiculously complex system of houses and kingdoms—and a fully fleshed-out made-up language. Once you get the hang of who’s who, though, it becomes way easier to follow and impossible to put down. Plus, then you can be one of those people who humble brag complains about how Ser Jorah Mormont looks nothing like he's supposed to.

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hardest books ever dante
Cover: Signet Classics; Background: Twenty20

Inferno by Dante Alighieri

The first part of the 14th-century epic poem The Divine Comedy, Inferno tells the story of Dante’s journey through the nine circles of hell (you know, greed, fraud, gluttony, et cetera), as guided by the Roman poet Virgil. It’s ultimately an allegory for man’s search for spiritual enlightenment, but the difficulty in reading Inferno comes from the incredibly in-depth historical and theological background that’s far from common knowledge. If you can read it in the original Italian, you have our eternal respect. If not, try to find a translation that’s heavy on contextual notes (we like John Ciardi’s) and delight in Dante’s biting satire and occasionally utterly twisted mind.

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hardest books ever joyce
Cover: CreateSpace Independent Publishing Platform; Background: Twenty20

A Portrait of the Artist as a Young Man by James Joyce

Joyce’s first novel, published in 1916, is the modernist Künstlerroman (basically, the coming of age of an artist) of Stephen Dedalus, Joyce’s fictional alter ego and an allusion to Daedalus, the craftsman and artist of Greek mythology. Mixing third person narrative and free indirect speech (where a character's voice is partly mediated by the voice of the author), Joyce details Stephen’s religious and intellectual awakening. No offense to Ulysses or Finnegan’s Wake, but if you read one work by Joyce, make it this.

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hardest books ever ishiguro
Cover: Vintage; Background: Twenty20

Never Let Me Go by Kazuo Ishiguro

Warning: This novel will reduce you to tears…once you figure out what’s going on. An atypical dystopian sci-fi, Ishiguro’s remarkably subtle 2005 novel imagines what life would be like if you were a clone, born to have your organs harvested in early adulthood. The catch is, the whole carer-donor thing (the book’s main premise) is never really explicitly defined, making for an interesting, slow and tragic reveal. If you stick with it, it will stick back with you for a long time.

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hardest books ever bible
Cover: Zondervan; Background: Twenty20

The Bible by Various Authors

Heard of it? Widely considered to be the best-selling book of all time (we’re talking upwards of five billion copies), The Bible is as open to interpretation as it is long, and we’ll leave it at that.

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