Naked Lunch by William S Burroughs
One of the most famously incomprehensible works of the 20th century, Naked Lunch was Burroughs’ attempt to relate his drug-fueled experiences in Tangier and the various other places he holed up during the 1950s to indulge his appetite for strong narcotics and young gentlemen. The result is a disconnected, surreal narrative that involves drugs, a talking asshole, lots of paranoia, more drugs, and carnivorous homosexual creatures called Mugwumps. And drugs. Lots of drugs.
Finnegans Wake by James Joyce
What, you thought Ulysses was confusing? Pah! Compared to Finnegans Wake, Joyce’s account of Leopold Bloom’s meanderings through Dublin makes for positively light reading. Honestly, we’re not going to pretend that we’re better than anyone else — we couldn’t make head or tail of Finnegans Wake, and we’re always surprised when someone claims that they can.
A Clockwork Orange by Anthony Burgess
Yes, of course, we know that it’s meant to be incomprehensible. But that doesn’t make A Clockwork Orange any easier to navigate — the droogs’ impenetrable and alienating slang means that finding a way into the novel is difficult in the extreme. This doesn’t mean that it’s not a fantastic book, of course – but it’s definitely hard work.
Trainspotting by Irvine Welsh
Similarly, the narrative of Trainspotting isn’t particularly confusing — it jumps around a bit, and it’s occasionally hard to tell who’s actually narrating, but generally it’s easy enough to follow. The prose, however… Until you get into the swing of reading phonetically rendered Edinburgh slang, you might as well be reading an obscure Norwegian dialect for all you can understand what’s going on. Persevere, though, and read out loud to yourself if necessary — go on, ignore the looks the people on the subway are giving you. Curiously enough, you do end up getting used to the way Welsh writes, and it’s worth it.
The Sound and The Fury by William Faulkner
Although the plot of The Sound and The Fury isn’t complex, the manner in which it’s related makes it difficult to follow — particularly the first part of the novel, which is narrated in an entirely non-linear chronology by a character who suffers from autism. The remaining three parts relate the same sequence of events from different viewpoints, leaving it to the reader to piece together their own interpretation of what actually happened. It’s one of those books that you really need to read twice — the first time, it’s thoroughly confusing, but the second, everything suddenly makes sense.
The Life and Opinions of Tristram Shandy, Gentleman by Laurence Sterne
When a novel takes three volumes to reach the birth of its hero, you know that it’s not exactly going to allow for a quick skim-read. And when those three books involve said hero’s apparently random musings on pretty much any subject that seems to come to mind, you start to wonder quite what you’ve let yourself in for. Not so much incomprehensible as rambling and unruly, Tristram Shandy was way ahead of its time, but its lack of structure and its vernacular can be a struggle for modern readers.
Gravity’s Rainbow by Thomas Pynchon
Pynchon’s never been the easiest of authors, but even his fans and literary supporters were taken aback by the labyrinthine and constantly mystifying nature of his 1973 epic Gravity’s Rainbow. The book encompasses some 400 characters, a narrative structure that has something to do with squares on a sheet of graph paper, a hyperactive prose style that can be challenging enough even without the 400 characters and the squares, and a plot that traces the trajectory of a German V-2 rocket. Yes. It’s confusing, alright.
Underworld by Don DeLillo
There’s a stretch of several hundred pages in the middle of Don DeLillo’s epic novel where it seems like a new character is introduced every few pages — both real historical figures like J. Edgar Hoover and entirely fictional characters — and none of them seem to have any connection to any of the others. It’s like flicking through a cosmic phonebook and reading the life stories of the people you find therein. Of course, all these characters are interconnected, and by the time Underworld draws to a close — 821 pages after it began — you have some idea as to how the whole thing ties together. For most of the novel, however, you’re find yourself continuing dutifully by virtue of a) an appreciation of DeLillo’s prose and b) a vague hope that at some point, somehow, you might work out what’s actually going on.
Foucault’s Pendulum by Umberto Eco
Umberto Eco’s debut The Name of the Rose was a rollicking and thoroughly entertaining period novel that managed to encompass both an involving story and an impressive amount of historical detail. Its follow-up Foucault’s Pendulum was an interminable, turgid load of pretentious nonsense about the Illuminati, the Knights Templar, and the Holy Grail. If a gazillion-page upscale version of The Da Vinci Code – shot through with literary in-jokes and rendered in prose that’s apparently an ongoing attempt to regurgitate the contents of a thesaurus – sounds like your idea of a good time, then read away. If not, we advise steering clear.
Atlas Shrugged by Ayn Rand
Actually, despite its size and its pseudo-intellectual airs, the only incomprehensible thing about Atlas Shrugged is why people still insist on reading it. As opposed to, y’know, throwing it against a wall. Or beating Rush Limbaugh around the head with it.