33 Challenging Books To Read For The Bragging Rights — Because Sometimes You Just Want To Be Able To Say You Finished It

As an English major, I witnessed a phenomenon unique to that field of study: Students would often brag about which difficult or obscure books they had read, or were reading, or were writing about. James Joyce was a favorite, and the mere mention of Finnegans Wake became a running joke. The bragging was all good-natured, often tempered further with sheepish grins and mannerisms. "Yeah, I read that," we'd laugh. "It's a bad idea, let me tell you." 

For those of you also forced to deal with snobbish a-bags, I've compiled this list of 33 books you can read for bragging rights — many of which also happen to be quite good. I know it isn't right to stoop to their level, but sometimes you have to fight fire with fire. Read a few of the entries on this list, and name drop them the next time Stuffed Shirt McTweed gets a little haughty.

Image: Jackie Waters


'One Hundred Years of Solitude' by Gabriel García Márquez

One Hundred Years of Solitude is one of the shorter novels on this list, but it makes up for what it lacks in length with dense prose and obscure — to many U.S. readers — historical references. Although it’s probably Márquez’s most well-known book, with Love in the Time of Cholera as a close second, you can almost certainly bet that the anyone you meet who has read it will be only other person at the party with those qualifications.

Excerpt: Many years later, as he faced the firing squad, Colonel Aureliano Buendía was to remember that distant afternoon when his father took him to discover ice. At that time Macondo was a village of twenty adobe houses, built on the bank of a river of clear water that ran along a bed of polished stones, which were white and enormous, like prehistoric eggs. The world was so recent that many things lacked names, and in order to indicate them it was necessary to point.”

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'Atlas Shrugged' by Ayn Rand

At 1200 pages in paperback, Atlas Shrugged is a massive ode to author Ayn Rand’s philosophy of objectivism. It was published to lukewarm reviews in 1957, and the only folks reading it today are devout libertarians and college students desperate for scholarships. If you’ve made it through this thick pile of wood pulp, feel free to brag about it.

Excerpt: ”Only the man who does not need it, is fit to inherit wealth–the man who would make his own fortune no matter where he started. If an heir is equal to his money, it serves him; if not, it destroys him. But you look on and you cry that money corrupted him. Did it? Or did he corrupt his money?”

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'Infinite Jest' by David Foster Wallace

Since its publication in 1996, David Foster Wallace’s Infinite Jest has become a staple for twenty-somethings looking to challenge themselves with a bit of light summer reading. It’s a brilliantly postmodern novel, and name-dropping it will inevitably elicit awe from some corners and eye-rolling from others.

Excerpt: ”The woman, a 46-year-old-Boston accountant with irreversible restenosis of the heart, responded so well to the replacement of her defective heart with a Jarvik IX Exterior Artificial Heart that within weeks she was able to resume the active lifestyle she had so enjoyed before stricken, pursuing her active schedule with the extraordinary prosthesis portably installed in a stylish Etienne Aigner purse. The heart’s ventricular tubes ran up to shunts in the woman’s arms and ferried life-giving blood back and forth between her living, active body and the extraordinary heart in her purse.”

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'Nightwood' by Djuna Barnes

Nightwood isn’t particularly imposing, but T.S. Eliot insisted readers needed a poetic bent in order to properly appreciate it. Author Djuna Barnes’ work is on the fringes of modernism — known to academics and knowledgeable laypersons, but barely recognizable in the mainstream — so you’ll pick up some obscurity points by reading this one.

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. Yes, we who are full to the gorge with misery should look well around, doubting everything seen, done, spoken, precisely because we have a word for it, and not its alchemy.”

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'Finnegans Wake' by James Joyce

I’m not exaggerating when I say that Finnegans Wake is the Holy Grail of difficult-to-read books. While James Joyce isn’t an easy writer to read, by any means, this novel stands apart as nigh unreadable. It took him seventeen years to finish, possibly because he had to practically invent a new language in which to write it.

Excerpt: “The great fall of the offwall entailed at such short notice the pftjschute of Finnegan, erse solid man, that the humptyhillhead of humself prumptly sends an unquiring one well to the west in quest of his tumptytumtoes: and their upturnpikepointandplace is at the knock out in the park where oranges have been laid to rust upon the green since devlinsfirst loved live.”

'Tender Buttons' by Gertrude Stein

Tender Buttons isn’t a long book, but it’s certainly more difficult than much of Gertrude Stein’s other work. It’s a collection of poems, many of which don’t look like poems at all. Wide open to interpretation, Tender Buttons will be one of the most difficult modernist pieces you ever read.

Excerpt: “The change the dirt, not to change dirt means that there is no beefsteak and not to have that is no obstruction, it is so easy to exchange meaning, it is so easy to see the difference. The difference is that a plain resource is not entangled with thickness and it does not mean that thickness shows such cutting, it does mean that a meadow is useful and a cow absurd.”

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'A Brief History of Time' by Stephen Hawking

OK, so A Brief History of Time is not difficult to read or understand. At all. Renowned scholar Stephen Hawking deliberately presents his history of astronomy and physics simply and in a format that laypersons can easily understand. But since many aren’t actually aware of the book’s purpose, saying you’ve read it will still net you some nerdy brownie points.

Excerpt: ”As far as Kepler was concerned, elliptical orbits were merely an ad hoc hypothesis, and a rather repugnant one at that, because ellipses were clearly less perfect than circles. Having discovered almost by accident that elliptical orbits fit the observations well, he could not reconcile them with his idea that the planets were made to orbit the sun by magnetic forces.”

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'The Female Man' by Joanna Russ

The Female Man is part of the feminist science fiction tradition, but it’s wildly unapproachable, and much more so than other books in the genre. It’s often difficult to tell who is speaking to whom, and the narration can seem out of sync with the book’s events. If you endure Joanna Russ’ novel, you can pat yourself on the back for reading a book that’s both difficult and obscure.

Excerpt: “As the bear swore in Pogo after having endured a pot shoved on her head, being turned upside down while still in the pot, a discussion about her edibility, the lawnmowering of her behind, and a fistful of ground pepper in the snoot, she then swore a mighty oath on the ashes of her mothers (i.e. her forebears) grimly but quietly while the apples from the shaken apple tree above her dropped bang thud on her head:

OH, SOMEBODY ASIDES ME IS GONNA RUE THIS HERE PARTICULAR DAY.”

'Gravity's Rainbow' by Thomas Pynchon

Thomas Pynchon’s Gravity’s Rainbow has all the makings of a truly challenging read. Huge cast of characters? Check. Complex narrative? Check. Heavy influence on pop culture in general? Check. Overly-lengthy sentences? Check.

Excerpt: ”Bloat is one of the co-tenants of the place, a maisonette erected last century, not far from the Chelsea Embankment, by Corydon Throsp, an acquaintance of the Rossettis’ who wore hair smocks and liked to cultivate pharmaceutical plants up on the roof (a tradition young Osbie Feel has lately revived), a few of them hardy enough to survive fogs and frosts, but most returning, as fragments of peculiar alkaloids, to rooftop earth, along with manure from a trio of prize Wessex Saddleback sows quartered there by Throsp’s successor, and dead leaves off many decorative trees transplanted to the roof by later tenants, and the odd unstomachable meal thrown or vomited there by this or that sensitive epicurean-all got scumbled together, eventually, by the knives of the seasons, to an impasto, feet thick, of unbelievable black topsoil in which anything could grow, not the least being bananas. Pirate, driven to despair by the wartime banana shortage, decided to build a glass hothouse on the roof, and persuade a friend who flew the Rio-to-Ascension-to-Fort-Lamy run to pinch him a sapling banana tree or two, in exchange for a German camera, should Pirate happen across one on his next mission by parachute.”

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'To the Lighthouse' by Virginia Woolf

Virginia Woolf isn’t a particularly difficult author to read, but To the Lighthouse is the exception that proves the rule. It isn’t unreadable, but it is quite lyrical, and that quality may slow some readers’ progression through the novel.

Excerpt: ”Also the sea tosses itself and breaks itself, and should any sleeper fancying that he might find on the beach an answer to his doubts, a sharer of his solitude, throw off his bedclothes and go down by himself to walk on the sand, no image with semblance of serving and divine promptitude comes readily to hand bringing the night to order and making the world reflect the compass of the soul.”

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'Cloud Atlas' by David Mitchell

David Mitchell’s books consistently pop up on awards nomination lists, and Cloud Atlas — the basis for the 2012 film of the same name — is no different. In it, Mitchell weaves together six disparate stories, from the 19th century to far in the future. Additionally, the novel ties into the author’s other works.

Excerpt: ”In the rude shipyard beneath my window, work progresses on the jibboom, under Mr. Sykes’s directorship. Mr. Walker, Ocean Bay’s sole taverner, is also its principal timber merchant & he brags of his years as a master shipbuilder in Liverpool. (I am now versed enough in Antipodese etiquette to let such unlikely truths lie.)”

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'The Clan of the Cave Bear' by Jean M. Auel

The Clan of the Cave Bear is the first novel in an impressive series, in which author Jean M. Auel seeks to accurately portray interactions between Neanderthals and Cro-Magnons. Auel’s novel is well-researched, although archaeological and anthropological research has since rendered some of the author’s source information obsolete. The novel aims big, and doesn’t fall short, making it a daunting read.

Excerpt: ”The lean-to, perched on the far edge of the abyss, tilted, as half the solid ground beneath it pulled away. The slender ridgepole teetered undecidedly, then collapsed and disappeared into the deep hole, taking its hide cover and all it contained with it. The girl trembled in wide-eyed horror as the foul-breathed gaping maw swallowed everything that had given meaning and security to the five short years of her life.”

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'Ulysses' by James Joyce

This is the second Joyce novel to make this list. Ulysses is the beginning of the author’s well-known, experimental style. Saying that the book spans only 228 pages and roughly 24 hours in the lives of its characters doesn’t do justice to its challenge. 

Excerpt: ”Listener: reclined semilaterally, left, left hand under head, right leg extended in a straight line and resting on left leg, flexed, in the attitude of Gea-Tellus, fulfilled, recumbent, big with seed. Narrator: reclined laterally, left, with right and left legs flexed, the index finger and thumb of the right hand resting on the bridge of the nose, in the attitude depicted in a snapshot photograph made by Percy Apjohn, the childman weary, the manchild in the womb.”

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'Bodies That Matter' by Judith Butler

Judith Butler’s Bodies That Matter came near the end of an era in which academic works were not seen as worthy unless they were hair-rippingly difficult to read. The book is a brilliant treatise on gender discourse, but its thick language and lengthy sentences make for a slow read.

Excerpt: “Although the political discourses that mobilize identity categories tend to cultivate identifications in the service of a pol itical goal, it may be that the persistence of disidentification is equally crucial to the rearticulation of democratic contestation. Indeed, it may be precisely througl; practices which underscore disidentification with those regulatory norms by which sexual difference is materialized that both feminist and queer politics are mobilized.”

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'War and Peace' by Leo Tolstoy

By now, War and Peace has achieved a kind of legendary difficulty. When you talk about dense and lengthy work, this Russian novel inevitably becomes part of the conversation. In paperback, Leo Tolstoy’s infamous novel is 1296 pages of masterpiece.

Excerpt: ”The unpleasant impression, like the remains of fog in a clear sky, passed over the emperor’s young and happy face and disappeared. He was somewhat thinner that day, after his illness, than on the field of Olmütz, where Bolkonsky had seen him for the first time abroad, but there was the same enchanting combination of majesty and mildness in his beautiful gray eyes, and the fine lips had the same possibility of various expressions, with a prevalent expression of good-natured, innocent youth.”

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'The House of Mirth' by Edith Wharton

Much of the difficulty in reading The House of Mirth comes from its emulation of older novels, such as the works of Jane Austen. Passages are lengthy, overly-worded, and depict social traditions that may be unknown to readers who have not studied Victorian customs.

Excerpt: ”It was a Monday in early September, and he was returning to his work from a hurried dip into the country; but what was Miss Bart doing in town at that season? If she had appeared to be catching a train, he might have inferred that he had come on her in the act of transition between one and another of the country-houses which disputed her presence after the close of the Newport season; but her desultory air perplexed him.”

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'Blood Meridian' by Cormac McCarthy

After a cool initial reception, Cormac McCarthy’s Blood Meridian is regarded today as the author’s masterpiece … now if only critics could figure out its message. McCarthy himself refuses to comment on the novel, leaving room for wider confusion and disagreement. Read it and see what you think.

Excerpt: ”That night they were visited with a plague of hail out of a faultless sky and the horses shied and moaned and the men dismounted and sat upon the ground with their saddles over their heads while the hail leaped in the sand like small lucent eggs concocted alchemically out of the desert darkness. When they resaddled and rode on they went for miles through cobbled ice while a polar moon rose like a blind cat’s eye up over the rim of the world. In the night they passed the lights of a village on the plain but they did not alter from their course.”

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'Meeting the Universe Halfway' by Karen Barad

Karen Barad’s Meeting the Universe Halfway ties together quantum physics, sociology, and feminism. If that doesn’t simultaneously intrigue and intimidate you, I don’t know what will.

Excerpt: “One of the fascinating aspects of the gedanken experiments that Bohr and Einstein considered is that they test the realm of the ‘metaphysical’­ that which lies beyond the physical domain. Questions about the nature of reality and of knowledge — such as ‘If no one measures a property of an object, does it exist?’ — are fair game in the imaginary laboratory of the mind. One does not rely on empirical evidence to adjudicate competing claims. Superior argumentation wins the day.”

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'The English Patient' by Michael Ondaatje

This long, award-winning novel from Sri Lankan-Canadian author Michael Ondaatje follows four individuals — and their complex relationships — living in a single home during World War II. Flashing back and forth between the title character’s memories and current events, the narrative of The English Patient is more challenging than its syntax and semantics.

Excerpt: “The desert could not be claimed or owned — it was a piece of cloth carried by winds, never held down by stones, and given a hundred shifting names long before Canterbury existed, long before battles and treaties quilted Europe and the East. Its caravans, those strange rambling feasts and cultures, left nothing behind, not an ember. All of us, even those with European homes and children in the distance, wished to remove the clothing of our countries. It was a place of faith.”

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'The Tale of Genji' by Shikibu Murasaki

The Tale of Genji is the first novel ever written. Let that sink in for a moment. It has no real plot; the story progresses through the lives of the characters as they grow up, grow old, and die. What’s more, the characters are never named, but are instead referred to by their status or title: signifiers that change as time passes.

Excerpt: “At the court of the Emperor (he lived it matters not when) there was among the many gentlewomen of the Wardrobe and Chamber one who, though she was not of very high rank, was favored far beyond all the rest; so that the great ladies of the Palace, each of whom had secretly hoped that she herself would be chosen, looked with scorn and hatred upon the upstart who had dispelled their dreams.”

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'Our Lady of the Flowers' by Jean Genet

Our Lady of the Flowers consists of various stories the narrator tells himself, often for sexual gratification. It’s a streaming novel, filled with deconstructed debauchery and Parisian gaiety, celebrated by French philosophers and the American Beat poets.

Excerpt: “But now I am afraid. The signs pursue me and I pursue them patiently. They are bent on destroying me. Didn’t I see, on my way to court, seven sailors on the terrace of a cafe, questioning the stars through seven mugs of light beer as they sat around a table that perhaps turned; then, a messenger boy on a bicycle who was carrying a message from god to god, holding between his teeth, by the metal handle, a round, lighted lantern, the flame of which, as it reddened his face, also heated it? So pure a marvel that he was unaware of being a marvel. Circles and globes haunt me: oranges, Japanese billiard balls, Venetian lanterns, jugglers’ hoops, the round ball of the goalkeeper who wears a jersey. I shall have to establish, to regulate, a whole internal astronomy.”

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'Wuthering Heights' by Emily Brontë

Emily Brontë’s Wuthering Heights is a popular classic, but that doesn’t mean it’s particularly easy to read. Each of the somewhat sizable cast of characters has deeply complicated relationships with the others, and this alone can make the novel daunting. Add in Brontë’s Victorian Gothic prose, and you’ve got a difficult read ahead.

Excerpt: “Young Earnshaw was altered considerably in the three years of his absence. He had grown sparer, and lost his colour, and spoke and dressed quite differently; and, on the very day of his return, he told Joseph and me we must thenceforth quarter ourselves in the back-kitchen, and leave the house for him.”

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'The Corrections' by Jonathan Franzen

Oprah may have selected this novel for her book club, but don’t think it’s a light read. The Corrections tells the tale of a Midwestern married couple, the Lamberts, whose children have all moved East and away from their parents’ traditions, only to be brought back by their father’s declining health.

Excerpt: ”Three in the afternoon was a time of danger in these gerontocratic suburbs of St. Jude. Alfred had awakened in the great blue chair in which he’d been sleeping since lunch. He’d had his nap and there would be no local news until five o’clock. Two empty hours were a sinus in which infections, bred. He struggled to his feet and stood by the Ping-Pong table, listening in vain for Enid.”

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'Passing' by Nella Larsen

Nella Larsen’s Passing is one of the greatest novels of the Harlem Renaissance. In it, black characters pass for white, while gay and lesbian characters pass for straight. Everyone is coerced to be something they aren’t. The complex social mores Larsen explores make Passing a tough, if short, read.

Excerpt: “But it couldn’t last, this verbal feat. Gertrude shifted In her seat and fell to fidgeting with her fingers. Irene, bored at last by all this repetition of the selfsame things that she had read all too often in papers, magazines, and books, set down her glass and collected her bag and handkerchief. She was smoothing out the tan fingers of her gloves preparatory to putting them on when she heard the sound of the outer door being opened and saw Clare spring up with an expression of relief saying: ‘How lovely! Here’s Jack at exactly the right minute. You can’t go now, ‘Rene dear.’”

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'The Sound and the Fury' by William Faulkner

What can you say about a book with one third-person narrator and three first-person narrators, one of whom slips between the present and the past, often, and without warning? The Sound and the Fury is a wonderful novel, but one that is difficult to follow through on reading.

Excerpt: ”I wasn’t crying, but I couldn’t stop. I wasn’t crying, but the ground wasn’t still, and then I was crying. The ground kept sloping up and the cows ran up the hill. T. P. tried to get up. He fell down again and the cows ran down the hill. Quentin held my arm and we went toward the barn. Then the barn wasn’t there and we had to wait until it came back. I didn’t see it come back. It came behind us and Quentin set me down in the trough where the cows ate. I held on to it. It was going away too, and I held to it.”

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'The Age of Innocence' by Edith Wharton

Although the previous Wharton novel we discussed emulates Austen’s romantic manners stories, both The House of Mirth and The Age of Innocence explore the lives of upper-class New Yorkers in the late-19th century. In this book, a public scandal threatens to ruin the engagement of two prominent socialites. As in The House of Mirth, obscure social customs complicate the novel for today’s readers.

Excerpt: “It was Madame Nilsson’s first appearance that winter, and what the daily press had already learned to describe as ‘an exceptionally brilliant audience’ had gathered to hear her, transported through the slippery, snowy streets in private broughams, in the spacious family landau, or in the humbler but more convenient ‘Brown coupé.’ To come to the Opera in a Brown coupe was almost as honourable a way of arriving as in one’s own carriage; and departure by the same means had the immense advantage of enabling one (with a playful allusion to democratic principles) to scramble into the first Brown conveyance in the line, instead of waiting till the cold-and-gin congested nose of one’s own coachman gleamed under the portico of the Academy.”

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'The Recognitions' by William Gaddis

The Recognitions is a tome, to put it mildly, about an aspiring minister-turned-forger whose paintings carry the novel with their religious and mythic symbolism. It’s a complex, tangled book, with a darkly introspective narrative.

Excerpt: ”Clarity’s essential, and detail, no fake mysticism, the facts are bad enough. But we’re embarrassed for people who tell too much, and tell it without surprise. How does he know what happened? unless it’s one unshaven man alone in a boat, changing I to he, and how often do you get a man alone in a boat, in all this … all this … Listen, there are so many delicate fixtures, moving toward you, you’ll see.”

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'The Making of Americans' by Gertrude Stein

Gertrude Stein’s The Making of Americans is an almost mockingly traditional story of two families, beginning with their immigrations to the U.S. and following their marriages, childbirths, and deaths over several decades. It’s an exploration into the American psyche, frequently told in a stream-of-consciousness style that, even for those used to reading it, can easily confuse.

Excerpt: ”The boy went to bed then and then the father when he got up in the early morning saw a wonderfully beautiful moth in the room and he caught him and he killed him and he pinned him and he woke up his son then and showed it to him and he said to him see what a good father I am to have caught and killed this one, the boy was all mixed up inside him and then he said he would go on with his collecting and that was all there was then of discussing and this is a little description of something that happened once and it is very interesting.”

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'Paradise Lost' by John Milton

In a newly-formed Hell, Satan becomes an eloquent, revolutionary hero. John Milton’s epic Paradise Lost is a fantastic story told in ten books, but few have read more than excerpts. Being more than casually familiar with the poem is the mark of a studious reader.

Excerpt: “Inhabitant with God, now know I well
  Thy favour, in this honour done to man,
  Under whose lowly roof thou hast voutsaf’t
  To enter, and these earthly fruits to taste,
  Food not of Angels, yet accepted so,
  As that more willingly thou couldst not seem
  At Heav’ns high feasts to have fed: yet what compare?”

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'Near to the Wild Heart' by Clarice Lispector

From Brazilian author Clarice Lispector comes this stream-of-consciousness novel that revolutionized Portuguese-language literature. Bearing a striking resemblance to earlier Modernist works, Near to the Wild Heart passes back and forth in the life of one woman, weaving an introspective narrative.

Excerpt: “Her father’s typewriter went clack-clack … clack-clack-clack … The clock awoke in dustless tin-dlen. The silence dragged out zzzzzz. What did the wardrobe say? clothes-clothes-clothes. No, no. Amidst the clock, the typewriter and the silence there was an ear listening, large, pink and dead. The three sounds were connected by the daylight and the squeaking of the tree’s little leaves rubbing against one another radiant.”

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'Foucault's Pendulum' by Umberto Eco

The mere title of Foucault’s Pendulum is enough to strike fear in the hearts of English majors, who are all too familiar with French philosopher and critic Michel Foucault. But fear not, because Umberto Eco’s novel title actually references a theory of planetary rotation from French physicist Léon Foucault … OK, maybe that’s not actually all that comforting.

Excerpt: “Above her head was the only stable point in the cosmos, the only refuge from the damnation of the panta rei, and she guessed it was the Pendulum’s business. A moment later the couple went off – he, trained on some textbook that had blunted his capacity for wonder, she, inert and insensitive to the thrill of the infinite, both oblivious of the awesomeness of their encounter – their first and last encounter – with the One, the Ein-Sof, the Ineffable. How could you fail to kneel down before this altar of certitude?”

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'Crime and Punishment' Fyodor Dostoyevsky

Like Tolstoy’s War and Peace, Fyodor Dostoyevsky’s Crime and Punishment is another starred entry in the annals of difficult literature. The novel’s protagonist tries to sort out the balance of good deeds and wrongful ones, and theorizes about his own purpose in life. It’s a dense, dark story, fraught with symbolism — and one you won’t be able to stop talking about.

Excerpt: “She had not even noticed the cruelty of his words. (The significance of his reproaches and his peculiar attitude to her shame she had, of course, not noticed either, and that, too, was clear to him.) But he saw how monstrously the thought of her disgraceful, shameful position was torturing her and had long tortured her. ‘What, what,’ he thought, ‘could hitherto have hindered her from putting an end to it?’ Only then he realized what those poor little orphan children and that pitiful half-crazy Katerina Ivanovna, knocking her head against the wall in her consumption, meant for Sonia.”

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'The Second Sex' by Simone de Beauvoir

What does it mean to be a woman, biologically? Spiritually? Historically? French feminist Simone de Beauvoir examines womanhood from nearly every imaginable discipline, resulting in one of the most prominent social examinations of femaleness ever written. Previously available in abridged English translations, The Second Sex has now been translated and published in its entirety. 

Excerpt: “When Hercules sat at the feet of Omphale and helped with her spinning, his desire for her held him captive; but why did she fail to gain a lasting power? To revenge herself on Jason, Medea killed their children; and this grim legend would seem to suggest that she might have obtained a formidable influence over him through his love for his offspring. In Lysistrata Aristophanes gaily depicts a band of women who joined forces to gain social ends through the sexual needs of their men; but this is only a play. In the legend of the Sabine women, the latter soon abandoned their plan of remaining sterile to punish their ravishers. In truth woman has not been socially emancipated through man’s need — sexual desire and the desire for offspring — which makes the male dependent for satisfaction upon the female.”

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