1. Finnegans Wake by James Joyce (1939) What makes it challenging: There's no clear plot — it's all stream of consciousness, filled with idiosyncratic language, free association, and an overall attempt to capture the feeling of dreams. After seven decades, Joyce scholars continue to argue over what it all means.Excerpt: "Sir Tristram, violer d'amores, fr'over the short sea, had passencore rearrived from North Armorica on this side the scraggy isthmus of Europe Minor to wielderfight his penisolate war: nor had topsawyer's rocks by the stream Oconee exaggerated themselse to Laurens County's gorgios while they went doublin their mumper all the time: nor avoice from afire bellowsed mishe mishe to tauftauf thuartpeatrick: not yet, though venissoon after, had a kidscad buttended a bland old isaac: not yet, though all's fair in vanessy, were sosie sesthers wroth with twone nathandjoe." 2. The Sound and the Fury by William Faulkner (1929) What makes it challenging: The style is stream of consciousness with three different narrators and one third-person section. The first narrator is mentally disabled to the extent that he cannot process linear time and jumps between past and present mid-sentence.Excerpt: "Caddy held me and I could hear us all, and the darkness, and something I could smell. And then I could see the windows, where the trees were buzzing. Then the dark began to go in smooth, bright shapes, like it always does, even when Caddy says that I have been asleep." 3. The Canterbury Tales by Geoffrey Chaucer (14th Century) What makes it challenging: You'll never forget where you were when you learned that Shakespearean language is actually Modern English. That's right — there was an English centuries before that's even harder to understand. Chaucer's collection of stories are often read translated, because the original is such a chore.Excerpt: "A knyght ther was, and that a worthy man, That fro the tyme that he first biganTo riden out, he loved chivalrie,Trouthe and honour, fredom and curteisie.Ful worthy was he in his lordes werre,And therto hadde he riden, no man ferre,As wel in cristendom as in hethenesse,And evere honoured for his worthynesse." 4. One Hundred Years of Solitude by Gabriel García Márquez (1967) What makes it challenging: Few family sagas stretch as wide as that of the Buendía clan — there are seven generations depicted here. As if that's not confusing enough, names are frequently repeated (basically ever character is named Aureliano). And oh yeah, try reading it in Spanish.Excerpt: "He sank into the rocking chair, the same one in which Rebecca had sat during the early days of the house to give embroidery lessons, and in which Amaranta had played Chinese checkers with Colonel Gerineldo Marquez, and in which Amarana Ursula had sewn the tiny clothing for the child, and in that flash of lucidity he became aware that he was unable to bear in his soul the crushing weight of so much past." 5. Gravity's Rainbow by Thomas Pynchon (1973) What makes it challenging: Quantum mechanics, mass extinction, speculative metaphysics — this is heavy stuff. It doesn't help that Pynchon's style is free-flowing and flashback-heavy. This has been called the definitive postmodern novel, which tells you everything you need to know.Excerpt: "Darkness invades the dreams of the glassblower. Of all the unpleasantries his dreams grab in out of the night air, an extinguished light is the worst. Light in his dreams, was always hope: the basic moral hope. As the contacts break helically away, hope turns to darkness, and the glassblower wakes sharply tonight crying, Who? Who?" 6. The Female Man by Joanna Russ (1975) What makes it challenging: There are multiple narrators throughout the novel's nine chapters and various subdivisions, but it's never clear who is speaking. (There are some clues. Good luck with that.) With the point of view changes, there are also confusing shifts in place and time.Excerpt: "Of course you don’t want me to be stupid, bless you! you only want to make sure you’re intelligent. You don’t want me to commit suicide; you only want me to be gratefully aware of my dependency. You don’t want me to despise myself; you only want the flattering deference to you that you consider a spontaneous tribute to your natural qualities." 7. Being and Time by Martin Heidegger (1927) What makes it challenging: If you are looking for a straightforward explanation of existentialism, hermeneutics, and deconstruction, this is not the book for you. Reading it in a college course is bad enough — trying to understand it on your own is nearly impossible. Why must philosophy be so dense?Excerpt: "But 'nowhere' does not mean nothing; rather, region in general lies therein, and disclosedness of the world in general for essentially spatial being-in. Therefore, what is threatening cannot come closer from a definite direction within nearness, it is already 'there' — and yet nowhere. It is so near that it is oppressive and takes one’s breath — and yet it is nowhere." 8. Our Lady of the Flowers by Jean Genet (1943) What makes it challenging: The classic queer novel about a drag queen named Divine — yes, the inspiration for the frequent John Waters collaborator — is lyrical and free-flowing. It's beautiful to listen to (especially in the original French) but tough to follow.Excerpt: "Ariadne in the labyrinth. The most alive of worlds, human beings with the tenderest flesh, are made of marble. I strew devastation as I pass. I wander dead-eyed through cities and petrified populations." 9. Infinite Jest by David Foster Wallace (1996) What makes it challenging: It's nearly 1100 pages. That aside, the novel is incredibly complex, with 388 endnotes — some of which also have footnotes. It's not impossible to get through, but it is a serious undertaking. And of course, there's the added pressure that this is one of those books you just have to read.Excerpt: "That sometimes human beings have to just sit in one place and, like, hurt. That you will become way less concerned with what other people think of you when you realize how seldom they do. That there is such a thing as raw, unalloyed, agendaless kindness. That it is possible to fall asleep during an anxiety attack. That concentrating on anything is very hard work." 10. Moby-Dick by Herman Melville (1851) What makes it challenging: The stuff about the white whale is fine, but there are several chapters — seriously so many — dedicated to whales and whaling. In high school, your teacher might let you skip them, but you're not really reading Moby-Dick until you know how spermaceti is gathered.Excerpt: "This whale, among the English of old vaguely known as the Trumpa whale, and the Physeter whale, and the Anvil Headed whale, is the present Cachalot of the French, and the Pottsfich of the Germans, and the Macrocephalus of the Long Words. He is, without doubt, the largest inhabitant of the globe; the most formidable of all whales to encounter; the most majestic in aspect; and lastly, by far the most valuable in commerce; he being the only creature from which that valuable substance, spermaceti, is obtained." 11. The Silmarillion by J. R. R. Tolkien (1977) What makes it challenging: Did you read The Lord of the Rings and think, "This needs way more backstory?" No, because you're a sane person. But just in case, The Silmarillion offers a complete mythological history of Tolkien's universe, and lo, it is dense.Excerpt: "With Manwë dwells Varda, Lady of the Stars, who knows all the regions of Eä. Too great is her beauty to be declared in the words of Men or of Elves; for the light of Ilúvatar lives still in her face. In light is her power and her joy. Out of the deeps of Eä she came to the aid of Manwë; for Melkor she knew from before the making of the Music and rejected him, and he hated her, and feared her more than all others whom Eru made." 12. Blood Meridian by Cormac McCarthy (1985) What makes it challenging: You know you're in for something difficult when the prose is described as both "sparse" and "expansive." McCarthy doesn't use quotation marks or apostrophes, and he refuses to grant any interviews about the novel. Figure it out yourself, basically.Excerpt: "The truth about the world, he said, is that anything is possible. Had you not seen it all from birth and thereby bled it of its strangeness it would appear to you for what it is, a hat trick in a medicine show, a fevered dream, a trance bepopulate with chimeras having neither analogue nor precedent, an itinerant carnival, a migratory tentshow whose ultimate destination after many a pitch in many a mudded field is unspeakable and calamitous beyond reckoning. " 13. The Corrections by Jonathan Franzen (2001) What makes it challenging: Now hear me out — there are likely plenty of Franzen fans shaking their fists right now, but his novel (however great) is truly dense. While readers may ease into the style, it's initially rather slow-going, to say the least.Excerpt: "By now it had been ringing for so many hours that the Lamberts no longer heard the message of ‘bell ringing’ but, as with any sound that continues for so long that you have the leisure to learn its component sounds (as with any word you stare at until it resolves itself into a string of dead letters), instead heard a clapper rapidly striking a metallic resonator, not a pure tone but a granular sequence of percussions with a keening overlay of overtones; ringing for so many days that it simply blended into the background except at certain early-morning hours when one or the other of them awoke in a sweat and realized that a bell had been ringing in their heads for as long as they could remember; ringing for so many months that the sound had given way to a kind of metasound whose rise and fall was not the beating of compression waves, but the much, much slower waxing and waning of their consciousness of the sound." 14. The Magic Mountain by Thomas Mann (1924) What makes it challenging: There's a lot of ambiguity, what with the novel shifting between realism and grand symbolic and mythological themes. It's a constant back-and-forth between plot and allegory, and while Mann knew it was tough, he refused to offer any clues as to how to understand the work.Excerpt: "The first step toward evil, toward desire and death, was taken precisely then, when there took place that first increase in the density of the spiritual, that pathologically luxuriant morbid growth, produced by the irritant of some unknown infiltration; this, in part pleasurable, in part a motion of self-defense, was the primeval stage of matter, the transition from the insubstantial to the substance. This was the Fall." 15. Atlas Shrugged by Ayn Rand (1957) What makes it challenging: It's largely an allegory for Objectivism, so if you don't subscribe to Ayn Rand's philosophy, making it through the lengthy novel is an unbearable chore. Don't forget the 70-page speech that ends up being a significant chunk of the book.Excerpt: "The man who refuses to judge, who neither agrees nor disagrees, who declares that there are no absolutes and believes that he escapes responsibility, is the man responsible for all the blood that is now spilled in the world. Reality is an absolute, existence is an absolute, a speck of dust is an absolute and so is a human life. Whether you live or die is an absolute. Whether you have a piece of bread or not, is an absolute. Whether you eat your bread or see it vanish into a looter's stomach, is an absolute." 16. Ulysses by James Joyce (1922) What makes it challenging: The so-called greatest novel of all time might not be as impenetrable as Joyce's Finnegans Wake, but it's no easy task either. Inspired by The Odyssey, it contains a staggering 30,030 different words, and endless puns, allusions, and stylistic curiosities.Excerpt: "Yes when I put the rose in my hair like the Andalusian girls used or shall I wear a red yes and how he kissed me under the Moorish wall and I thought well as well him as another and then I asked him with my eyes to ask again yes and then he asked me would I yes to say yes my mountain flower and first I put my arms around him yes and drew him down to me so he could feel my breasts all perfume yes and his heart was going like mad and yes I said yes I will yes." 17. Underworld by Don DeLillo What makes it challenging: Not only is Underworld non-linear — it spans from the 1950s through the 1990s, referencing contemporary historical events through disparate characters and intertwined themes. Even some of the most highbrow critics agree that it's too long.Excerpt: "He drove into the spewing smoke of acres of burning truck tires and the planes descended and the transit cranes stood in rows at the marine terminal and he saw billboards for Hertz and Avis and Chevy Blazer, for Marlboro, Continental and Goodyear, and he realized that all the things around him, the planes taking off and landing, the streaking cars, the tires on the cars, the cigarettes that the drivers of the cars were dousing in their ashtrays--all these were on the billboards around him, systematically linked in some self-referring relationship that had a kind of neurotic tightness, an inescapability, as if the billboards were generating reality." 18. Nightwood by Djuna Barnes (1936) What makes it challenging: As T.S. Eliot puts it in the introduction, "Only sensibilities trained on poetry can wholly appreciate it." By which he means, this modernist novel is dense as hell. It's important for its frank depictions of homosexuality, but that doesn't make it any less of an ordeal.Excerpt: "We are but skin about a wind, with muscles clenched against mortality. We sleep in a long reproachful dust against ourselves. We are full to the gorge with our own names for misery. Life, the pastures in which the night feeds and prunes the cud that nourishes us to despair. Life, the permission to know death. We were created that the earth might be made sensible of her inhuman taste; and love that the body might be so dear that even the earth should roar with it." 19. Simulacra and Simulation by Jean Baudrillard (1981) What makes it challenging: With a title this daunting, it's no surprise Baudrillard's philosophical treatise is tough to digest. In addressing the relationship between reality and symbols, the philosopher exposes society while confusing the hell out of readers fighting a losing battle with postmodernism.Excerpt: "We will live in this world, which for us has all the disquieting strangeness of the desert and of the simulacrum, with all the veracity of living phantoms, of wandering and simulating animals that capital, that the death of capital has made of us — because the desert of cities is equal to the desert of sand — the jungle of signs is equal to that of the forests—the vertigo of simulacra is equal to that of nature — only the vertiginous seduction of a dying system remains, in which work buries work, in which value buries value — leaving a virgin, sacred space without pathways, continuous as Bataille wished it, where only the wind lifts the sand, where only the wind watches over the sand." 20. The Castle by Franz Kafka (1926) What makes it challenging: Kafka never finished it, which doesn't help. That aside, it's complicated — the protagonist is known only as "K." and the entire novel is a surrealistic take on alienation and bureaucracy. You'd have a much easier time with Kafka's short stories.Excerpt: "He speaks to Klamm, but is it Klamm? Isn’t it rather someone who merely resembles Klamm? Perhaps at the very most a secretary who is a little like Klamm and goes to great lengths to be even more like him and tries to seem important by affecting Klamm’s drowsy, dreamlike manner." 21. Absalom, Absalom! by William Faulkner (1936) What makes it challenging: Quentin Compson isn't the most reliable narrator — you might remember him from The Sound and the Fury — especially when he's telling a story to his roommate who keeps interrupting. As with most Faulkner novels, there are multiple points of view, and the truth is repeatedly obscured as the characters (and the reader) struggle to get the whole picture.Excerpt: "I, the dreamer clinging yet to the dream as the patient clings to the last thin unbearable ecstatic instant of agony in order to sharpen the savor of the pain’s surcease, waking into the reality, the more than reality, not to the unchanged and unaltered old time but into a time altered to fit the dream which, conjunctive with the dreamer, becomes immolated and apotheosized." 22. The Name of the Rose by Umberto Eco (1980) What makes it challenging: This is a novel of semiotics, the study of signs. Semiotics students use it to explain what they do — and I still have no idea what that is exactly. In some ways, The Name of the Rose is a straightforward mystery, but with complicated postmodernist elements.Excerpt: "Until then I had thought each book spoke of the things, human or divine, that lie outside books. Now I realized that not infrequently books speak of books: it is as if they spoke among themselves. In the light of this reflection, the library seemed all the more disturbing to me." 23. Cloud Atlas by David Mitchell (2004) What makes it challenging: In many ways, Mitchell's novel is easier than the others on the list — it's engaging and very readable. At the same time, it moves from the nineteenth century to a post-apocalyptic future, with a series of interconnected stories that end abruptly, then are finished in reverse chronological order.Excerpt: "Belief, like fear or love, is a force to be understood as we understand the theory of relativity and principals of uncertainty. Phenomena that determine the course of our lives. Yesterday, my life was headed in one direction. Today, it is headed in another. Yesterday, I believe I would never have done what I did today. These forces that often remake time and space, that can shape and alter who we imagine ourselves to be, begin long before we are born and continue after we perish." 24. To the Lighthouse by Virginia Woolf (1927) What makes it challenging: Plot? What plot? I mean, it's there, but this is a novel about philosophical introspection, with a plot that kind of happens in the background and is very hard to follow. There is minimal dialogue and action, because the whole thing is so internal.Excerpt: "She had known happiness, exquisite happiness, intense happiness, and it silvered the rough waves a little more brightly, as daylight faded, and the blue went out of the sea and it rolled in waves of pure lemon which curved and swelled and broke upon the beach and the ecstasy burst in her eyes and waves of pure delight raced over the floor of her mind and she felt, It is enough! It is enough!" 25. The Recognitions by William Gaddis What makes it challenging: Different characters are interwoven throughout the main narrative, which is loose to begin with. Gaddis admitted that his novel was "not reader-friendly." That's an understatement. Jonathan Franzen (who appears on this list) called The Recognitions the most difficult book he'd ever voluntarily read.Excerpt: "What is real, then? Nothing's real to you that isn't part of your own past, real life, a swamp of failures, of social, sexual, financial, personal...spiritual failure. Real life. You poor bastard. You don't know what real life is, you've never been near it. All you have is a thousand intellectualized ideas about life. But life? Have you ever measured yourself against anything but your own lousy past? Have you ever faced anything outside yourself? Life! You poor bastard." Have you suffered through a challenging book that didn't make the list? Add yours in the comments.