Introducing Difficult Books, A Descriptive List

October 29, 2009 | 2 books mentioned 69 2 min read

Whether scholars, creative writers, or citizen book lovers, most readers agree on a canon of certain legendarily difficult books—books that are hard to read for their length, or their syntax and style, or their structural and generic strangeness, or their odd experimental techniques, or their abstraction.  This post inaugurates a new Millions series devoted to identifying and describing these most difficult books: ones we’ve read/wrangled with ourselves, ones we’ve known students to struggle with time and again, ones that, more simply, “everyone knows” are hard to read—those works whose mere titles glisten with an aura of rarefied impenetrability.

covercovercovercoverThere will, doubtless, be those readers who look scornfully on our choices (“Psh. These aren’t that hard, you’re just not smart enough to read them“). Indeed, for myself, that is probably true. And to those so brilliant that not a one of these tomes challenged or vexed them more than a People magazine, we tip our hats.  This list is for the mere mortals among us—who have found themselves reading and rereading the same paragraph of James Joyce’s Ulysses to no avail, who have been reduced to tears by Faulkner’s one-line chapter, “My mother is a fish,” in As I Lay Dying, who may have spitefully broken the brittle spine of her first used copy of Tristram Shandy, who use a volume of Gibbon’s History of the Decline and Fall of the Roman Empire as a doorstop and eye it with a wary distrust when she walks past it (for it is fond of stubbing toes).

But this is also a list for those who, after breaking the spine, picked up the wounded volume, taped it back together, and finished that infuriating chapter, and another, and another… until, triumph!, it was finished at last. And, perhaps, now that we think on it again, having finished, could it be that it was worth the struggle? Could it be that in the pain of it was a tinge of pleasure, of value (not to mention pride)?

The hope is that our series will eventually be exhaustive, and because this is a series and so on-going, we welcome your suggestions. Where we can, we also offer our advice to aspiring readers of a particular difficult work. Our descriptions aim to be modest primers for those about to embark on the reading of a difficult book, as well as small, memorial essays on these (by many measures) great books. Titles will come from many eras and genres—the Renaissance, the eighteenth and nineteenth centuries, the high Modernism of the early twentieth century, and finally our own time, and we include fiction, poetry, philosophy, and critical theory. Titles will be primarily those written in English, but in some cases we include translations. Future posts will cover works by Immanuel Kant, G.W. F. Hegel, Marcel Proust, Robert Musil, James Joyce, Ezra Pound, Virginia Woolf, Gertrude Stein,  Djuna Barnes, William Vollmann, Thomas Pynchon, Jacques Derrida, David Foster Wallace, Joseph McElroy, Donna Harraway, William H. Gass, William Gaddis, and others.

1621: The Anatomy of Melancholy by Robert Burton
1667: Paradise Lost by John Milton
1704: A Tale of a Tub by Jonathan Swift
1747-8: Clarissa by Samuel Richardson
1759-67: The Life and Opinions of Tristram Shandy, Gentleman by Laurence Sterne
1851: Moby Dick by Herman Melville
1922-62: The Cantos by Ezra Pound
1927: To the Lighthouse by Virginia Woolf
1964: The Sonnets by Ted Berrigan
1969: The Dream Songs by John Berryman
1969: Ada, or Ardor by Vladimir Nabokov
1974: Dhalgren by Samuel R. Delany

is a staff writer for The Millions living in Virginia. She is a winner of the Virginia Quarterly's Young Reviewers Contest and has a doctorate from Stanford. Her writing has appeared in The Washington Times, In Character, VQR, Arts & Letters Daily, and The Daily Dish.


  1. William Gass’s The Tunnel is just brutal, but the people I know who have finished it claim that it’s one of the best things they’ve ever read. Go figure.

  2. I’m one of those people, Saul. I think that should be the front cover blurb: “Just brutal.”

  3. most frustrating and difficult book for me was Women and Men by Mcelroy, i was never able to crack the code and enter the world. Most challenging books to me are like a maze or like learning a new language, with sustained effort i can usually sort of solve it or start to understand it’s rythms and then it flows pretty well, but Women and Men just completely eluded me. Only Revolutions was a little like that for me too but i didn’t try as hard, the whole structure thing i found annoying, i don’t really want to have to put in manual labor while reading.

  4. I found My Name is Red, for all its richness, an incredibly difficult book. The most brutal book I’ve ever read, however, remains the slim Narrative of Sojourner Truth.

  5. After forcing myself to read Ulysses about a dozen years ago because of all the best-book-of-the-20th-century hype I decided slogging through a long book that you are not enjoying is stupid.
    So, after about 50 pages of Infinite Jest I decided it was the new Ulysses and unceremoniously put it down.

  6. The Death of Virgil by Hermann Broch. I have read the English translation, which “unfolds” the German into a confusing hypnotic and intoxicating reading. Very difficult and quite rewarding.

  7. I found _Women and Men_ though it took a year to finish it, a novel that has grown on me over time, and it changed the way I looked at how sentences can be written. McElroy’s humanity and compassion, attributes not easily spotted amongst Usian or other post-modernists, are evident in this book as he tries to show his characters living on multiple levels, just like we do in our daily lives. Forster’s “only connect” came repeatedly to mind as I read this book, and his most recent, _Actress in the House_, which is similar but easier to understand.

    Difficult? Yes. Readable and eventually comprehensible? Also yes. It requires patience and interest. McElroy’s not for everyone, perhaps, but few writers are.

  8. Nice to see Gass mentioned, though if anyone ever wanted a reason to read Burton, Woolf, Gaddis, Musil, Kant, Joyce, (and authors not on the above list), Alfau, O’Brien, Elkin, Mann… ah, the list goes on, Gass’s books of loving criticism are a good place to start.

    And the Tunnel is amazing. Wish there was someone of Gass’s abilities to speak for the Tunnel.

  9. I think Michael Brodsky is probably the most demanding novelist I’ve read, followed closely by Robbe-Grillet, Gaddis, early Beckett and Malcolm Lowry. I recommend cleansing your palate in between difficult books with Richard Yates, whose style is so limpid that it almost feels like you’re not reading.

  10. Tristram Shandy is laugh aloud funny. I picked it up a few years ago with no prior knowledge–just wanted a novel from the 18th C. It’s a real treat. At one point, Sterne gets 8 pp. out of a piping hot chestnut falling into a guy’s breeches. This is lofty stuff.

    As for difficult, I nominate JR by Wm. Gaddis. Seven hundred pages, virtually all dialog with no attributions. You have to pretend you’re sitting in a dark room with headphones on, listening to unidentified voices–but soon you recognize who’s talking. There are also, on the Web, guides that will break it all down into scenes by page. This book is a hoot. You just have to let it have its way with you.

  11. At Swim -Two -Birds was unscalable for me. I’ve climbed Ulysses, The Recognitions, Gravity’s Rainbow, Tristram Shandy and enjoyed them all, but O’Brien leaves me gasping.

  12. For sheer length, Richardson’s Clarissa should be a contender here. It’s supposedly the longest book ever written in English.

    And though it wasn’t difficult to read, the 12-volume Dance to the Music of Time by Anthony Powell should also qualify. It took me from November 2007 until June 2009 to get through the whole thing, but I took some long breaks from it.

  13. I must second the nomination for Samuel Richardson’s Clarissa. When I first started it, I thought I would never finish. It is now my favorite book and I have read it many times. For cunning, wit, pure wickedness, and above all, charm, few villains in English literature equal Robert Lovelace.

  14. Add to your list (or reading list): Thomas Carlyle’s Sartor Resartus.Difficult, wonderfully bizarre.

  15. Though I love all of his stuff, it will do many readers a service to take a look at The Master’s last three: The Ambassadors, The Wings of the Dove and especially, The Golden Bowl. Pages would go by and I would not have known what he was saying.

  16. “Mulligan Stew” by Gilbert Sorrentino was just about worth the read with some wonderful jousts with language. The sum greater than the parts? Probably not.

  17. Clarissa isn’t that challenging – it’s essentially a bodice ripper dressed up as moral improvement. But it is loooong. That’s the trouble, right there.

  18. Hands down has to be The Waves by Virginia Woolf. Utterly, totally and completely batshit crazy and baffling from start to finish.

  19. Don’t forget Patrick White. Murky, baroque, and baffling, with flashes of brilliance that keep you reading in the hope that all will eventually become clear…which it never does.

  20. I found Fredric Jameson “The Cultural Logic of Late Capitalism” to still be a little out of my reach a few years back. I am getting ready to try it out again… It should be a bit more accessible in light of the understanding I have gained since my last whack at it.

  21. All books by Gerald Murnane, if you can find them, are fascinating. Obscure and fascinating. One feels as though the grit in one’s reading eye has been thoroughly cleaned out with…something. They are fictions, sometimes_about_ the act of writing, in many cases, though not always.
    He has a newie, Barley Patch, available from Giramondo Press in Australia, that opens, “Must I write?” As my kids might say, intense.

  22. Carlyle’s a good suggestion. And how about Samuel R. Delaney’s Dhalgren? Still working on that one…

  23. If we’re chucking in works of philosophy (Kant, Hegel, et al.), surely Wittgenstein’s Tractatus goes flying in at the top? Head-in-the-microwave hard.

  24. During my late teens I devoured ‘Wolf Solent’ by John Cowper Powys, identifying powerfully with the author’s depiction of the protagonist’s inner world. Subsequently I choked on Cowper Powys’ magnum opus, ‘A Glastonbury Romance’ and the various other Cowper Powys doorsteps over which I attempted to clamber with increasing dispmay. I now have a modest collection of John Cowper Powys first editions, none of which I have read beyond their indigestible first few pages.

  25. thank god someone else mentioned the difficulty of as i lay dying! i thought I was the only one. i’d also like to nominate the man without qualities, and for something more contemporary, 2666. I read the first four books and just couldnt bring myself to finish the fifth.

  26. Kirk, please give Infinite Jest five or six weeks of your attention – it’s a rich, rewarding book. Just keep three bookmarks inside it (one to mark your place in the text, one for the endnotes and one for words to look up). I finished it last weekend and haven’t been able to pick up anything else since. Nothing I’ve read describes entertainment or addiction so clearly and thoroughly.

  27. Faulkner’s Absalom, Absalom! is one of the few books I’ve ever thrown across a room from frustration. I picked it up and continued, threw it across the room again, picked it up again … and now it’s my answer to anybody when they ask me my favorite American novel. As with so many “difficult” books, once you figure your way in, once you begin to get a foothold, then the magic starts.

  28. William Gaddis’ “JR” is indeed difficult and wonderful but even more complex, and again all dialogue with no character identification was his next one, “A Frolic of His Own,” which takes on the American’s craze for suing one another to the nth degree.
    But for sheer intensity of writing, I suggest “Miss MacIntosh, My Darling” by Marguerite Young, two volumes (Dalkey Archive Press), 1300 pages of paragraphless prose poetry and essentially plot-less. It’s that aspect that allows you decades to finish it (it took me four).
    It also happens to be one of Anne Tyler’s favorite books, which she says she dips into during episodes of writer’s block. The book even had a few seconds of fame in the film version of her “The Accidental Tourist.”

  29. Looking at the list of Difficult Books covered so far, it looks like they are going in chronological order. That means Ill have to wait for my favorites: Vollmann, Gass, and DFW.

  30. @Otto At Swim-Two-Birds harder than Ulysses?!? You must be joking. Without the footnotes, I never would have stood a chance with Ulysses. I never even felt the need for footnotes with O’Brien (and At Swim-Two-Birds is far and away his toughest book).

  31. ‘apologies for getting all epistemological, but “hard” is really (really) subjective in this context…..

  32. I read Ulysses at age 15, and I don’t regret it.
    Now I’m 16, and on to Gravity’s Rainbow.

  33. The Cat in the Hat really blew my preconceptions away.
    What is it with that tall, anthropomorphic, mischievous cat, wearing a tall, red and white-striped hat and a red bow tie.

  34. I have a few white whales that I will dominate. Did I miss it in the comments? Did no one mention Proust? I’ve read Swann’s Way, but I feel uncomfortable making that statement. I just don’t feel like I paid enough attention. Oh also, Auerbach’s Mimesis. Maybe one day, I’ll figure that one out.

  35. Sorry I just realize my previous first sentence made no sense. (I call the books that truly challenge me white whales…usually in my best grizzly old sea captain voice.)

  36. Have read 2/12: Moby-Dick and Paradise Lost. I have to say that, for me, both are superseded in difficulty by Bronte’s ‘Villette’. It’s long, jumps in and out of French during speeches, and has a very devious narrator — the reader has a task to work ahead of her.

  37. If “House of Leaves” by Mark Z. Danielewski is not on this list when its done, it cant be taken seriously…

  38. Ashamed to say I’ve read not a single one on that list…BUT (I saved a lot on my car insurance) I DID make it through The Royal Family by William Vollman. I’ll choose waterboarding next time.

  39. i am surprise that the bible is not number one , very difficult to read and everybody have a different interpretation

    it have all murder ,mystery, science fiction , mass murder ,jealousy ,erotic poems ,magic.

    plus not many have read it covert to covert , one problem though no jokes !

  40. I’ve read (and felt I understood) quite a few difficult philosophers like Derrida, Heidegger, Hegel, Adorno, Baudrillard and even Lacan, but nothing could get me through Being and Nothingness, by Sartre.

  41. Great project, sweet feeling of investment paying off when you have suffered through some entry on the list.

    If the flood gates are opened to french philosophy, well, there are many… but Lacan and his Écrits should definitly be considered. Derrida just need a friendly explanation, but Lacan never intended something as mundane as being understood. Even Zizek admits it: unreadable.

  42. I second two books: Darconville’s Cat-moreover, you
    reach the point of increasing returns.

    And Oswald Spengler’s Decline-the 2 volume unabridged set with fold-out
    charts will make for instant discombobulation.

    Also Laura Warholic by Theroux.

  43. I loved “Moby Dick” when I read it in the 1980s, but that was because I had the now out-of-print Harold Beaver edition from Penguin with its 300 pages of notes telling you what you need to know.
    I have loved the first 3 pages of “Ulysses” each and every time I have read them.
    Wittgenstein’s “Tractatus”, ugh.
    Carlyle’s “Sartor Resartus” is actually supposed to be funny, rather than impenetrable. Melville was inspired by Carlyle but lightened up the prose.
    Wright’s “Arabic Grammar” (Dover reprint) is easily the best Arabic grammar I know, but the author assumes the reader already reads Arabic, as well as German, French, Latin, Greek, Hebrew, Aramaic, Syriac, Coptic and Ethiopic, so people who had trouble with Spanish …

  44. I’d nominate Cloud Atlas, by David Mitchell, and The Illuminatus Trilogy, by Robert Anton Wilson and Shea. The former due to its postmodern and semi-experimental semiotics; the latter due to its length. The people I’ve met who have abandoned these works far outweigh those who have completed them.

    Cloud Atlas, however, is a higher achievement. Amazing work.

Add Your Comment:

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.