The 5 Most Difficult Books to Read

How many have you read?

moby dick on a kobo ereader, one of the most difficult books to read
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All of us, at one time or another, have been assigned books to read, either in high school or in college, that we… didn’t care for, let’s say. But no matter how much you may have hated reading The Great Gatsby or Catcher in the Rye, you can’t really argue that they were particularly difficult books to get through. They’re fairly short, and while they may be thematically dense – for good or ill – they’re also relatively quick reads.

Not so with the 5 books on this list. These are among the most difficult books to read, notable for the dread they often inspire in school curriculums, the complexity of their language, and the simple thickness of their spines. If you were ever assigned any of these books—or if you just made it through them on your own—then you’ve really accomplished something special.

Of course, difficult isn’t synonymous with “bad,” and while many of us may have dreaded being assigned some thematically dense, linguistically challenging doorstopper of a novel in class, there’s a reason why pretty much every book on this list is a well-regarded (and much-beloved) classic. It just doesn’t change the fact that they’re not always the easiest books to read…

Bleak House

Bleak House

By Charles Dickens

There’s a joke that makes the circles in many a college English department about Charles Dickens getting paid by the word—and you can certainly see why when you try to crack Bleak House, quite possibly his longest novel. (David Copperfield edges it out by wordcount, but Bleak House usually ends up with more pages, for various reasons.)

In proper Dickensian fashion, Bleak House is populated by a massive cast of characters, including no less than two narrators. Its elaborate story is filled with plots and subplots aplenty, and revolves around a complicated and seemingly intractable court case – which can certainly prove dry reading for many who attempt to approach the gargantuan tome, clocking in at around 900 pages long.

Also, as the title might imply, Bleak House can be, well… kind of bleak. Though it's sprinkled throughout with Dickens’ wit and sly humor, it’s also filled with poverty, injustice, and the kinds of social commentary that were Dickensian specialties. Which means that in addition to being a very long read, it’s also a bit of a grim one.

Related: 10 Charles Dickens Books Everyone Should Read

War and Peace

War and Peace

By Leo Tolstoy

What is there to say about Tolstoy’s classic War and Peace? It’s one of the longest and most ambitious books ever written, clocking in at well over 1,000 pages. That’s… a lot of reading, especially when it makes frequent digressions into Russian history and philosophy. Set during the Napoleonic Wars, it follows the lives of numerous characters, showing how war affects not only those fighting in it, but also those on the home front—themes that haven’t stopped resonating, even more than 150 years after its original publication. 

Though it’s been considered his greatest work, Tolstoy himself didn’t regard War and Peace as a novel in the true sense, saying that it is “not a novel, even less is it a poem, and still less a historical chronicle.” So what is it then? Difficult to read, certainly, as later chapters abandon narrative altogether to dive deep into matters of philosophical contemplation.

Moby Dick

Moby Dick

By Herman Melville

After those last couple of tomes, Herman Melville’s magnum opus feels positively brief by comparison, clocking in at a “mere” 720 pages. Those 720 pages are barnstormers, though. Widely considered one of the “Great American Novels,” Moby-Dick is jammed front-to-back with dense themes, poetic language, and plenty of nautical terminology that can leave more landbound readers all at sea. Despite that, it’s one of the most famous books in the world, and features one of literature’s best-known first lines: “Call me Ishmael.”

D. H. Lawrence called it “the greatest book of the sea ever written,” while William Faulkner said that it was a book he wished he had written himself. Not every person who tried to crack its often seemingly impenetrable tale of monomania and one man’s quest for a white whale has found the job an easy go, however, and even in Melville’s time the book was seen as a commercial failure, only attaining its great reputation after the author’s death.

ulysses, one of the most difficult books to read


By James Joyce

Like Moby Dick, James Joyce’s classic novel Ulysses is “only” around 720 pages long—it also travels a remarkably small distance, compared to many of the other books in this list, taking place on a single day within the city of Dublin, despite its thematic connection to Homer’s much more traditionally epic Odyssey.

Divided into sections and written in a dizzying array of styles, from stage play to stream-of-consciousness, Ulysses is a novel like no other, and is considered by many to be the “demonstration and summation of the entire movement” of modernist literature, a school with which Joyce was inextricably linked. Such formal boldness may make the book a dazzling example of the movement—and, in many estimations, of literature itself—but it doesn’t exactly make it an easy or simple book to read.

gravity's rainbow by thomas pynchon, a book with a famous first line

Gravity's Rainbow

By Thomas Pynchon

There is an exchange, in the 2019 film Knives Out, in which Benoit Blanc, our resident gentleman detective, mentions Gravity’s Rainbow by Thomas Pynchon. “I’ve never read it,” Marta Cabrera replies. “Neither have I,” Blanc says. “Nobody has.”

Despite its reputation for being, among other things, impenetrable, Gravity’s Rainbow was actually selected to receive the Pulitzer Prize for Fiction in 1974. It didn’t actually get the prize, however, when the advisory board deemed it “unreadable,” “overwritten,” and “turgid,” among other things. Instead, no Pulitzer Prize for Fiction was issued that year. 

Quite a legacy, and also a pretty good indication of why Gravity’s Rainbow tends to dominate lists of books that are difficult to read. Set at the end of World War II, the novel centers on the production of V-2 rockets and gets… pretty in-depth in the subject. The Literary Encyclopedia called it “the postmodern novel” and said that it redefined “both postmodernism and the novel itself.” A stunning accomplishment, perhaps, but not one that makes for casual beach reading.

Featured photo via Unsplash / Spencer