If you’ve made it all the way through any of these, give yourself a pat on the back. Bonus points if you actually understood what you were reading.
Finnegans Wake by James Joyce (1939)
What makes it challenging: There's no clear plot — it's 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 d'amores, fr'over 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 topsawyer's rocks by the stream Oconee exaggerated themselse to Laurens County's 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 all's fair in vanessy, were sosie sesthers wroth with twone nathandjoe."
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."
The Canterbury Tales by Geoffrey Chaucer (14th Century)
What makes it challenging: You'll never forget where you were when you learned that Shakespearean language is actually Modern English. That's right — there was an English centuries before that's even harder to understand. Chaucer's 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."
One Hundred Years of Solitude by Gabriel García Márquez (1967)
What makes it challenging: Few family sagas stretch as wide as that of the Buendía clan — there are seven generations depicted here. As if that's 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."
