Nightwood , Djuna Barnes
Frequently cited as one of the most difficult novels of all time, Barnes’ 1936 roman à clef broke barriers with its frank depictions of homosexuality. But that’s not what makes its 2013 reader tough — that’d be the prose, dense and intense, of which T.S. Eliot sniffed in the book’s introduction, “only sensibilities trained on poetry can wholly appreciate it.” And we all know poets are the toughest of all.
Blood Meridian , Cormac McCarthy
The Road was a contender for the obvious McCarthy spot, of course, for the unending bleakness of its journey-quest, but Blood Meridian is a nonstop nihilistic rampage filled with bloody scalps and other casual violence. For lovers of beautiful language who also happen to be strong of heart.
Moby-Dick , Herman Melville
There’s only so much discussion of whaling techniques and classifications that most readers can take. To those who sail through these chapters, the rest of the reading world salutes you.
Infinite Jest , David Foster Wallace
An obvious one, maybe, but anyone who can conquer the book that requires at least three bookmarks and a significant amount of negative capability is one tough cookie.
J R , William Gaddis
Seven hundred fifty-plus pages of pure dialogue with no real indication of who is speaking or how we’re getting from place to place! No, it’s not the worst story you’ve ever read in workshop; it’s a brilliant masterpiece. Also relevant here: The Recognitions, another masterpiece that will surely prove your mettle.
Finnegans Wake , James Joyce
If you can make sense out of Joyce’s famously incomprehensible novel, you must have a reading mind of steel. If you can get through it without making sense of it, that’s a whole different kind of tough altogether.
The Sound and the Fury , William Faulkner
Yes, it’s a classic, but it’s also a confusing one, packed with stream-of-consciousness narration that keeps changing place, time, and narrators on you. Fun fact: originally, Faulkner intended to use different-colored inks to signify the different temporal spaces, so readers armed only with the black-and-white paperback (i.e., everyone) are attempting a complex trip without the map.
Bad Behavior , Mary Gaitskill
All the tough girls are reading Mary Gaitskill, now and forever.
In Search of Lost Time , Marcel Proust
You don’t get off with the madeleine episode — only those who make it through all seven volumes can claim the tough-guy crown. But it’s a giant, elaborately spined, baroque crown, so it’s worth shooting for.
Alphabetical Africa , Walter Abish
Oh, Walter Abish. He’s not for everyone, though he does seem the tough and jaunty fellow himself, what with that eyepatch and flowing hair. In this novel, the first chapter contains only words that start with the letter A. The second, A or B. And so on. Maddening indeed — but not for you, right?
Geek Love , Katherine Dunn
There’s nothing difficult about the prose in Dunn’s cult novel — in fact, it zips right along. It’s more the novel’s stars, a group of increasingly demented circus freaks, and its overall strangeness that gets it on this list. Reading this novel feels like turning something not quite ripe over in your stomach for a week, while your mind delights.
Naked Lunch , William S. Burroughs
Speaking of not quite ripe: Burroughs’ cult classic will certainly mess with your stomach, not to mention your mind.
The Faerie Queene , Edmund Spenser
Technically a poem, sure. An epic Elizabethan allegorical poem, at that, that required Spenser to make up his own kind of stanza. That is truly wonderful — once you get past all the language barriers.
Trainspotting , Irvine Welsh
Here’s another novel that it takes a tough stomach to read: an a-linear, perspective-swapping jaunt into the lives of heroin addicts. How grimy is it? In 1993, it was longlisted for the Booker Prize, but barred from the shortlist after “offending the sensibilities of two judges.” Oh, dear me.
Pet Sematary , Stephen King
Dead things should usually stay dead. For those too tough to hide their books in the freezer before they go to sleep (or tough enough to admit to doing it).
Coin Locker Babies , Ryu Murakami
The first line of this surreal novel tells you (almost) all you need to know: “The woman pushed on the baby’s stomach and sucked its penis into her mouth; it was thinner than the American menthols she smoked and a bit slimy, like raw fish.” At once a disturbing coming-of-age story and an equally disturbing end-of-the-world tale, it’ll take a tough reader to blithely drink the water after closing this one.
Battle Royale , Koushun Takami
You need to be almost as tough to finish this book as you would have had to be to get out of its twisted battle arena alive. Almost. No points for watching the movie.
House of Leaves , Mark Z. Danielewski
Firstly, you’ll need a mirror. Secondly, you’ll feel like you’re trapped in an endless labyrinth. Suffice it to say, this book is not for the casual reader.
To The Lighthouse , Virginia Woolf
Another notoriously difficult classic, Woolf’s landmark of modernism and stream-of-consciousness not only examines the world but the way in which we perceive the world. And only the tough examine their own consciousness.
The Painted Bird , Jerzy Kosinski
There are scores of Holocaust novels that take a toll on the reader, but this one might just be the most harrowing of the bunch. Bleak and brutal and incredibly depressing, it follows a young Jewish boy as he encounters endless cruelty. Truly disturbing.
Wittgenstein’s Mistress , David Markson
But if disturbing Holocaust narratives aren’t your thing, maybe you’d consider one of Markson’s anti-novels? This reference- and philosophy-strewn text is presented as the ongoing narrative of the last woman on earth — who is, as you might expect, slightly mad. Heartbreaking and intellectually complicated is a tough double pill, but Markson makes it go down easy. Er, sort of.
Johnny Got His Gun , Dalton Trumbo
A World War I soldier wakes up in a hospital bed having lost all of his limbs and facial features, trapped in what’s left of his body, unable to move or, at first, communicate, or even kill himself. If you can live with him for 250 pages, and then the rest of your life, which is how long you’ll spend thinking about this book, you deserve a medal.
Dhalgren , Samuel R. Delany
Delany’s polarizing and much-discussed novel is a convoluted, circular puzzle, full of Greek mythology, texts-within-texts, and incredible language. You’ll either fight your way through it and throw it against the wall at the end (like a certain Harlan Ellison did) or fight your way through it and enshrine it as one of your all-time favorites.
The Making of Americans , Gertrude Stein
Stein’s “history of a family’s progress” is monstrous — both in length (900 pages plus) and in its importance as a modernist novel. Her trademark repetitious style and obliqueness might make your head swim at first blush, but it’s a beat all the tough kids are hip to.
The Silmarillion , J.R.R. Tolkien
For those who thought The Lord of the Rings was too short and didn’t have enough background into the world, we salute you.
Heart of Darkness , Joseph Conrad
Unlike many others on this list, Heart of Darkness is slim enough to fit in your coat pocket. But it’s dense, and as thick and sticky as the jungle, and many describe it as being nigh impenetrable without a knife to hack with. If you can do it with your bare hands, that’s when you know you’re tough. If not, well… The horror! The horror!
Hopscotch , Julio Cortazar
Not the toughest game around, hopscotch, but Cortazar’s novel gives it some serious street cred. After all, any novel that comes with a “Table of Instructions” is bound to pose some difficulties. Here, you get multiple endings, sections from other novels of questionable veracity, and at least 99 “expendable” chapters that the reader is invited to either indulge in or skip around (they’re skippable for a reason, but tough readers go for it). Hop to.
Out , Natsuo Kirino
You can always count on the Japanese to provide the most disturbing of books; in Kirino’s horrifying-but-amazing novel, a group of women working at a bento factory have to dispose of the body when one kills her husband in a fit of rage. Suffice it to say, no one gets out clean. Not a difficult read, but difficult to shake from one’s head, so let’s say that you’ll be tough if you sleep a full night after reading this one.
2666 , Roberto Bolaño
Long? Check. Difficult? Check. Descriptions of the methodical rapes of hundreds of women in Mexico? Check. The knowledge that it’s based on reality? Check. Hundreds of other questions that never get answered? Check x 100. This book is not for the casual reader.
Tampa , Alissa Nutting
If you can stomach the subject matter (the novel is told from the perspective of a completely unrepentant pedophile), you’ll zip through. The real toughness points go for reading it in public, though. It’s scandalous enough that the less brave might save it for private places.
War and Peace , Leo Tolstoy
The gold standard in long, dense, and Russian.
The Life and Opinions of Tristram Shandy, Gentleman , Laurence Sterne
Nothing says “tough guy” like the quintessential 18th-century meta-novel, complete with black pages, marbled pages, drawings, and more digressions than you can shake a stick at. Case in point: it takes three volumes to get to the protagonist’s birth.
Gravity’s Rainbow , Thomas Pynchon
Another notoriously difficult modern classic, Pynchon’s magnum opus seemingly seeks to encompass everything in the world, including coprophilia, quantum mechanics, and more characters than you can count. And that’s not even approaching Pynchon’s prose. One tough cookie, but worth every minute.
The Canterbury Tales , Geoffrey Chaucer
You know who was a pretty tough, kick-ass broad? The Wife of Bath. You know who else? Anybody who reads her tale, particularly in the original Middle English.
Underworld , Don DeLillo
Another day, another nonlinear, character-happy tome that will change your life and give you some serious biceps just from carrying it around.
Almanac of the Dead , Leslie Marmon Silko
This epic novel is sometimes meandering but wickedly intriguing, featuring a prophesied Native American insurrection, a brutally corrupt society (ours), and drugs and guns and the end of the world.
Cosmos , Witold Gombrowicz
In this surreal, rambunctiously existential novel, two young men living and working in Warsaw come across a sparrow deliberately hanged in a tree, and it sets them on a dubious path of discovery, attempting to track down the killer. This is a book that is as much philosophical exploration as it is story, and a work of genius, surely to only be fully understood by one. And hey, if genius isn’t tough, who knows what is?
The Conservationist , Nadine Gordimer
Another thing that’s pretty tough to read about (much less come to terms with as a historical reality): apartheid. With the possible exception of J.M. Coetzee’s Disgrace, no one cuts closer to the bone than the Nobel Prize-winning Gordimer, particularly in this powerful, intense book.
Sophie’s Choice , William Styron
Do you know what’s tough? Choices. Also, reading this book without crying.
Clarissa, Or the History of a Young Lady , Samuel Richardson
One of the very longest, and most difficult, novels in the English language is Richardson’s 1748 epistolary novel about a young girl trying to make something of herself. If you can get through this book, you can get through anything.
The Unfortunates , B.S. Johnson
Johnson is a master of the experimental form, and his “book in a box” — a set of unbound pages, the first and last chapters noted but the rest designed to be read in whatever order the reader chooses — is a masterful feat. It’s also a nightmare for those who just want to sit down with a story, and so only for those with curiosity and patience in spades.
The Collected Stories of Lydia Davis , Lydia Davis
Davis’ prose is like a scalpel, cutting tiny pieces out of you at every shrug of a swipe. But all those gestures add up, and one day you wake up with a new face.
The Tunnel , William Gass
Though not the most experimental of Gass’ brilliant work, The Tunnel may be the one that requires the most sheer grit to get through. Let’s refer to Michael Silverblatt of the LA Times, who put it perfectly, calling The Tunnel “[a] bleak, black book, it engenders awe and despair. I have read it in its entirety 4½ times, each time finding its resonance and beauty so great as to demand another reading. As I read, I found myself devastated by the thoroughness of the book’s annihilating sensibility and revived by the beauty of its language, the complexity of its design, the melancholy, horror and stoic sympathy in its rendering of what we used to call the human condition.”
The Year of Magical Thinking , Joan Didion
If you can get through Didion’s meditation on grief without the ink running because of all the crying you’ve been doing on its pages, that’s when you know you’re tough. Much like our lady of loss, who will never be bested or broken.
The Demon , Hubert Selby Jr.
Reading this book will necessitate a shower. But wait, it’s worth it. IF YOU’RE TOUGH.
The Royal Family , William T. Vollmann
Part biblical allegory, part crime novel, all 700 pages about perversion. This book will twist the world and twist all of your dearly held beliefs and then laugh. Laugh!
Divine Comedy , Dante Alighieri
Well, clearly this list couldn’t end without at least one more epic poem in there, this one written sometime in the early 1300s. If you’re reading this famous journey through the circles of hell just for funsies, you’re probably pretty much a badass.
A Tale of a Tub , Jonathan Swift
Probably the greatest and most difficult satire by one of the world’s most storied satirists.
The Castle , Franz Kafka
It takes a tough reader to deal with the endless alienation and isolation that is Kafka, and his final, unfinished novel is possibly the most alienating and isolating of all his works. That said, it’s pretty wonderful. Also of note and not heralded often enough: his short story “In the Penal Colony,” this writer’s favorite. Check it out.
The Gulag Archipelago , Aleksandr Solzhenitsyn
Oof. This novel is based on the author’s own experiences as a prisoner in a gulag labor camp. You may think the reading is tough, but you probably shouldn’t be complaining.