The Most Challenging Books to Read (And How to Finish Them)

Why it’s hard: Joyce spent seventeen years building a language out of puns in dozens of tongues. The book opens mid-sentence with “riverrun” and its last sentence runs back into its first, so there is no real beginning or end. It tops almost every list of the most challenging books for good reason.

Time: 40 hours or more. Many readers take months.

Tip: Read it aloud. It makes more sense heard than seen, and Joyce’s own 1929 recording of the “Anna Livia Plurabelle” passage shows how. Keep Campbell and Robinson’s A Skeleton Key to Finnegans Wake nearby.

Try it if: you have finished Ulysses and want to know where Joyce went next.

Why it’s hard: Heidegger coins his own terms, Dasein above all, and uses ordinary words in new senses. The book is also unfinished: he published only the first two divisions of a much larger plan.

Time: 40 hours plus, and most people reread.

Tip: Read it beside a guide. Hubert Dreyfus’s Being-in-the-World walks through Division I paragraph by paragraph.

Try it if: you want the source behind half of twentieth-century philosophy and are happy to study rather than read.

Why it’s hard: One day in Dublin, 16 June 1904, told in eighteen episodes that each change style: newspaper headlines, a play script, a question-and-answer catechism, a near-unpunctuated monologue. The vocabulary runs to about 30,000 different words.

Time: 30 to 40 hours.

Tip: Read a short summary of each episode before you start it, and keep Don Gifford’s Ulysses Annotated for the allusions.

Try it if: you like comic novels. Under the experiments, it is a very funny book.

Why it’s hard: A V-2 rocket story set at the end of the Second World War, with hundreds of named characters, sudden songs, rocket science and long paranoid digressions. In 1974 the Pulitzer fiction jury chose it and the advisory board refused, calling it unreadable among other things, so no fiction prize was given that year.

Time: 30 to 40 hours.

Tip: Accept confusion on a first pass and keep moving. Steven Weisenburger’s A Gravity’s Rainbow Companion explains the references page by page.

Try it if: you enjoy conspiracy, slapstick and big ideas in the same paragraph.

Why it’s hard: Only 180 pages, but almost every sentence is a knot of imagery. Much of it is given over to the extravagant monologues of Dr Matthew O’Connor. T.S. Eliot, who wrote the introduction, warned that readers trained on poetry would get the most from it.

Time: 5 to 7 hours, plus a reread.

Tip: Read it the way you would read poetry: slowly, a chapter at a sitting.

Try it if: you want an early, frank portrait of queer love in Europe and New York between the wars.

Why it’s hard: The first section is narrated by Benjy Compson, a man with a cognitive disability for whom past and present are the same. Time jumps without warning, often marked only by italics. Faulkner wanted the section printed in different coloured inks, and the Folio Society finally did it in 2012.

Time: 10 to 12 hours.

Tip: Push through Benjy, finish the book, then reread the first section. It opens up completely the second time.

Try it if: you want a short novel that rewards a second reading more than almost any other.

Why it’s hard: Seven volumes and about 1.27 million words, which makes it the longest novel by most counts. The sentences can run for a page, and whole chapters pass at a dinner party. Of all the most challenging books here, it asks for the most time.

Time: Over 100 hours. Most readers take a year.

Tip: Commit to the first volume, Swann’s Way, and decide from there. Lydia Davis’s translation of it is the easiest way in.

Try it if: you have a long holiday, or a long commute, and like books about memory and jealousy.

Why it’s hard: 1,079 pages with 388 endnotes, some of which have footnotes of their own. The story jumps between a tennis academy, a recovery house and Québécois separatists, and the chronology only settles once you decode the corporate-sponsored names of the years.

Time: 40 to 50 hours.

Tip: Use two bookmarks, one for the text and one for the endnotes, and read every note. The plot hides in them.

Try it if: addiction, entertainment and loneliness are subjects you want to sit with for a long time.

Why it’s hard: A family finds their house is bigger inside than out. That story comes to you as an academic study of a film that may not exist, annotated by a tattoo-parlour drifter who has his own breakdown in the footnotes. Pages run sideways, backwards and nearly blank, and the word “house” is printed in blue. It is the one horror novel among the most challenging books on this list.

Time: 20 to 25 hours.

Tip: Buy the print edition, not the ebook. The layout is the story.

Try it if: you want horror that makes you physically turn the book in your hands.

Why it’s hard: No quotation marks, untranslated Spanish, words most dictionaries have dropped, and violence on almost every page as a gang of scalp hunters crosses the 1840s borderlands. Harold Bloom admitted it took him two attempts.

Time: 10 to 12 hours.

Tip: Read in short sessions. The cruelty wears you down faster than the prose does.

Try it if: you want the darkest Western ever written and one of fiction’s great villains in Judge Holden.

Why it’s hard: A land surveyor known only as K. tries to reach the officials who summoned him, and never does. Kafka abandoned the book in 1922 and it stops mid-sentence. The difficulty is the frustration itself.

Time: 10 to 12 hours.

Tip: Choose Mark Harman’s translation, which follows Kafka’s own text more closely than the older Muir version. Students who need help writing about Kafka can find essay services compared on review sites such as Academichelp.

Try it if: you have ever spent a morning on hold with a call centre.

Why it’s hard: 827 pages that run mostly backwards from the 1990s to the 1950s, linked by a baseball, the ball Bobby Thomson hit for the winning home run in the 1951 Giants and Dodgers play-off. Characters drop out for hundreds of pages.

Time: 28 to 32 hours.

Tip: Note each section’s year as you go. The chronology is the map.

Try it if: you want a novel about the whole Cold War, from waste disposal to the bomb.

Why it’s hard: Almost nothing happens on the surface. The story lives inside the Ramsay family’s heads, and the short middle section, “Time Passes”, covers ten years and several deaths in a few pages.

Time: 6 to 8 hours.

Tip: Follow who is thinking, not what is happening. Our review of To the Lighthouse sets out the three parts.

Try it if: you want a short, achievable first step into the most challenging books of modernism.

Why it’s hard: A murder mystery in a 14th-century abbey, buried under theology, heresy debates and Latin that Eco left untranslated. He later said he made the first hundred pages slow on purpose, as a test of who should stay.

Time: 18 to 20 hours.

Tip: Get past page 100. After that the mystery takes over.

Try it if: you like detective fiction and libraries in equal measure.

Why it’s hard: The chase for the white whale is gripping. Between the chases come long chapters on whale anatomy, whaling law and the classification of whales, starting with “Cetology”.

Time: 18 to 22 hours.

Tip: Treat the whaling chapters as short essays. Read one a day alongside the story chapters.

Try it if: you want to see how a book that sold poorly in Melville’s lifetime became the great American novel.

Why it’s hard: Edited by Christopher Tolkien after his father’s death, it reads like scripture and chronicle rather than a novel, with thousands of years of history and many characters who go by two or three names.

Time: 12 to 15 hours.

Tip: Keep the family trees and the index of names open as you read. Our guide to Tolkien’s Middle-earth is useful background.

Try it if: The Lord of the Rings left you wanting the myths behind it.

Why it’s hard: Over 1,200 pages, hundreds of characters with Russian name forms and nicknames, passages in French, and long essays on the theory of history, most of all in the second epilogue.

Time: 35 to 45 hours.

Tip: Choose an edition with a character list, and allow yourself to skim the second epilogue on a first reading.

Try it if: you like family sagas. Most of the book is far more readable than its reputation.

Why it’s hard: Seven generations of the Buendía family in the town of Macondo, and the same few names, Aureliano and José Arcadio above all, keep coming back.

Time: 12 to 15 hours.

Tip: Use the family tree many editions print at the front, or sketch your own. Our review of One Hundred Years of Solitude covers what to expect.

Try it if: you want to know where magical realism became a household term.

Why it’s hard: 1,168 pages in the first edition, built to argue Rand’s Objectivism. Near the end John Galt gives a radio speech that lasts three hours in the story and over sixty pages on the page.

Time: 40 to 50 hours.

Tip: Read it as a thriller about a railway and a vanishing elite, and take the speech in sittings. Our Atlas Shrugged review has more.

Try it if: you want to argue about it afterwards, for or against.