1.

Finnegans Wake by James Joyce (1939)

What makes it challenging: Theres no clear plot its 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 damores, frover 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 topsawyers rocks by the stream Oconee
exaggerated themselse to Laurens Countys 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 alls 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: Youll never forget where you were when you learned
that Shakespearean language is actually Modern English. Thats right there was
an English centuries before thats even harder to understand. Chaucers 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 bigan
To 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 Garca
Mrquez (1967)
What makes it challenging: Few family sagas stretch as wide as that of the Buenda
clan there are seven generations depicted here. As if thats 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. Gravitys Rainbow by Thomas Pynchon (1973)
What makes it challenging: Quantum mechanics, mass extinction, speculative
metaphysics this is heavy stuff. It doesnt help that Pynchons 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 novels nine
chapters and various subdivisions, but its 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 dont want me to be stupid, bless you! you only want to
make sure youre intelligent. You dont want me to commit suicide; you only want
me to be gratefully aware of my dependency. You dont 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 ones 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. Its 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: Its nearly 1100 pages. That aside, the novel is incredibly
complex, with 388 endnotes some of which also have footnotes. Its not
impossible to get through, but it is a serious undertaking. And of course, theres 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 youre 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 youre a sane person. But just in case,
The Silmarillion offers a complete mythological history of Tolkiens universe, and lo,
it is dense.
Excerpt: With Manw dwells Varda, Lady of the Stars, who knows all the regions of
E. Too great is her beauty to be declared in the words of Men or of Elves; for the
light of Ilvatar lives still in her face. In light is her power and her joy. Out of the
deeps of E she came to the aid of Manw; 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 youre in for something difficult when the
prose is described as both sparse and expansive. McCarthy doesnt 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, its 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: Theres a lot of ambiguity, what with the novel shifting
between realism and grand symbolic and mythological themes. Its 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: Its largely an allegory for Objectivism, so if you dont
subscribe to Ayn Rands philosophy, making it through the lengthy novel is an
unbearable chore. Dont 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 looters
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 Joyces Finnegans Wake, but its 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 its 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 ashtraysall 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. Its important for its frank depictions of homosexuality, but that
doesnt 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, its no surprise Baudrillards
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 foreststhe 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 doesnt help. That aside,
its complicated the protagonist is known only as K. and the entire novel is a
surrealistic take on alienation and bureaucracy. Youd have a much easier time with
Kafkas short stories.
Excerpt: He speaks to Klamm, but is it Klamm? Isnt 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 Klamms drowsy, dreamlike manner.
21. Absalom, Absalom! by William Faulkner (1936)
What makes it challenging: Quentin Compson isnt the most reliable narrator you
might remember him from The Sound and the Fury especially when hes 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 pains
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, Mitchells novel is easier than the others
on the list its 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, its 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
Tagged: most challenging books to read, ayn rand, chaucer, cormac mccarthy, david foster wallace, densest books, djuna
barnes, franz kafka, gabriel garcia marquez, hardest books to read, heidegger, herman melville, james joyce, jean genet, joanna
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. Thats an understatement. Jonathan Franzen (who appears on this
list) called The Recognitions the most difficult book hed ever voluntarily read.
Excerpt: What is real, then? Nothings real to you that isnt part of your own past,
real life, a swamp of failures, of social, sexual, financial, personalspiritual failure.
Real life. You poor bastard. You dont know what real life is, youve 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
didnt make the list? Add yours in the comments.
russ, jonathan franzen, jrr tolkien, most challenging books, most complicated books, thomas mann, thomas pynchon, umberto
eco, virginia woolf, william faulkner