The most daunting books ever written... that you need to read
Some of the most challenging and difficult books ever to read.
Everyone has them; those thick tomes with tiny type that have edged open windows, propped up wobbly tables and weighed down loose paper.
You’ve done everything with them — except read them. They invoke fear. It’s their size, their daunting literary baggage, their impenetrable language — and the very real prospect that if we were to attempt them, we’d spend approximately 4.5 days re-reading passages and another 12 hours looking up obsolete words in the dictionary before suffering a crushing sense of defeat when we finally commit it back to the bookshelf.
But this is a call to arms: it’s time to unearth that hefty work of intellectual brilliance, blow off the dust and show those titans of literature who’s boss.
This is our list of the most daunting books of all time... that we think need to be read by all. These books do take a little patience and perseverance - and it might mean that you have to forgo doom-scrolling Twitter or TikTok for a little bit - but it'll be worth your time.
And if you are thinking, nope, never going to happen. Then please head over to our list of the best books under 100 pages now!
Most daunting books of all time
1. Moby-Dick By Herman Melville (1851)Buy from Amazon now
Page count: 720
What it’s about: The narrator joins a whaling ship captained by Ahab, who wants to catch a certain white whale (Moby-Dick) that took his leg. Despite long digressions about the whaling trade, Ahab’s descent into obsessional madness is gripping.
Why you should read it: It's a cracking adventure book for one, but look beyond the water's surface and there's a deep exploration into philosophy, history, science and much more.
First line: Call me Ishmael.
2. War And Peace By Leo Tolstoy (1869)Buy from Amazon now
What it’s about: The story of five aristocratic families during the French invasion of Russia, told (mostly) in the manner of modern historical fiction. Unfortunately it’s now popularly known as a bad punchline — “What are you writing, War And Peace?”
Why you should read it: The most daunting thing about War And Peace is its size, but break it down and you will be enveloped by the brilliant characters within. This is a story about how the people of Moscow decided to pretty much party when they knew Napoleon was knocking on their door to invade. Throughout the book the perspective shifts too, with narratives being passed along from character to character - a modern trope that makes the book feel fresh, some 150 years after it was written.
First line: “Well, Prince, so Genoa and Lucca are now just family estates of the Buonapartes.”
3. Crime And Punishment By Fyodor Dostoevsky (1866)Buy from Amazon now
Page count: 576
What it’s about: A young Russian intellectual living in poverty sells his possessions before killing his pawnbroker. His guilt turns the story into a psychological thriller about human conscience.
Why you should read it: The Russian names will get some getting used to (especially as everyone seems to have about five of them) but beyond that, this is a book that gets to the core of the human condition and why some people commit crimes and are punished, while others are seemingly not.
First line: On an exceptionally hot evening early in July a young man came out of the garret in which he lodged in S Place and walked slowly, as though in hesitation, towards K Bridge.
4. Ulysses By James Joyce (1922)Buy from Amazon now
Page count: 1,040
What it’s about: Two men — writer Stephen Dedalus and advertising canvasser Leopold Bloom — whose lives intertwine during the course of a single day in Dublin (16 June 1904). Except the ordinary is then turned extraordinary by Joyce’s refusal to shy away from anything, particularly the darker and ruder bits of humanity. Some people are put off by his continual style changes, but the language is crystal-clear.
Why you should read it: Take your time but the lyrical brilliance of James Joyce's words will captivate you. Yes, you made need a guide to get through the denser parts of the story (and scrub up on your knowledge of The Odyssey beforehand) but remember that Joyce wants you to find joy in being confused so it doesn't always have to make sense!
First line: Stately, plump Buck Mulligan came from the stairhead, bearing a bowl of lather on which a mirror and a razor lay crossed.
5. Don Quixote By Miguel De Cervantes (1615)Buy from Amazon now
Page count: 1,008
What it’s about: A comic tale of a humble man who fashions himself as a chivalrous knight and sets out on many adventures. In 2002, it was voted best novel by 100 modern authors.
Why you should read it: It's Paul Auster's favorite novel for one. But beyond that, its episodic structure means that you can take time with this one. Also, it's a book about someone who is unable to separate fact from fiction anymore. An apt allegory, then, for these 'post truth' times.
First line: Somewhere in La Mancha, in a place whose name I do not care to remember, a gentleman lived not long ago, one of those who has a lance and ancient shield on a shelf and keeps a skinny nag and a greyhound for racing.
6. Blood Meridian by Cormac McCarthy (1985)Buy from Amazon now
Page count: 351 pages
What it’s about: Seen by many as The Great American Novel, a teenager travels across the American southwest and northern Mexico, teaming up with a gang who are on a mission to rid America of Indigenous Americans.
Why you should read it: With one of the greatest villains of all time and writing that is compelling throughout, this is a brutal novel that's not for the faint-hearted.
First line: See the child. He is pale and thin, he wears a thin and ragged linen shirt. He stokes the scullery fire.
7. A Brief History Of Time By Stephen Hawking (1988)Buy from Amazon now
Page count: 256
What it’s about: The fundamental questions of physics and our existence tailored to a non-genius audience. Topics covered include gravity, black holes, the Big Bang and the nature of time. The book occupied the bestseller list for several years.
Why you should read it: Yes, it's a book about science but it's not written with scientists in mind. It boils down incredibly complicated theories about black holes and the like into digestible segments.
First line: A well-known scientist (some say it was Bertrand Russell) once gave a public lecture on astronomy.
8. Underworld By Don DeLillo (1997)Buy from Amazon now
Page count: 832
What it’s about: Nick Shay is a waste-management executive with a sinister past and a wife who’s having an affair. The novel spans his life, wider historical events and the lives of the famous, using a baseball as the constant link between people and time. A 2006 survey of authors and critics by The New York Times voted it runner-up for best American novel of the previous 25 years (Toni Morrison’s Beloved came first).
Why you should read it: Written by one of the greatest modern day American authors, DeLillo gets to the very heart of what make America tick, from baseball to Cold War paranoia and everything in between.
First line: He speaks in your voice, American, and there’s a shine in his eye that’s halfway hopeful.
9. Remembrance Of Things Past By Marcel Proust (1927)Buy from Amazon now
Page count: 2,656 (Parts I & II)
What it’s about: A narrator reflects on his life and tries to understand it. One of the longest novels ever written, it took Proust more than a decade to complete.
Why you should read it: Over 400 characters, some million plus words. Yes, this one is for those who are in it for the long run. Stick with it and you have prose that is genuinely funny in places, while playing with the concepts of identity and memory. We will also always have a soft spot when it comes to novels that are about the process of writing as well.
First line: For a long time I used to go to bed early.
10. Gravity's Rainbow by Thomas Pynchon (1973)Buy from Amazon now
What's it about: Among many complex, maddening strands of this non-linear novel, the main plot is about a group of individuals trying to uncover secrets of a secret rocket made by the Nazis near the end of WWII - which is told by way of myriad erections, flashbacks to the 1700s, flash forwards and anything else Pynchon decides to through into his primordial soup of a novel.
Why you should read it: It'll take some decoding but there is a lot of fun to be had in Pynchon's meta fiction. Maybe try one of his other books first, though, to get acquainted with the author - something like Inherent Vice.
First line: A screaming comes across the sky.
11. Foucault’s Pendulum By Umberto Eco (1988)Buy from Amazon now
Page count: 656
What it’s about: Three Italian editors play a game creating a super-conspiracy linking major events in European history, attracting attention from real conspiracy theorists who want to know the truth at all costs.
Why you should read it: If you want to understand just how and why people get caught up in conspiracy theories, then this is the book for you. It's utterly evocative how the narrative is spun connecting big moments in history, even if you feel like you've entered a dark QAnon forum.
First line: That was when I saw the Pendulum.
12. Infinite Jest By David Foster Wallace (1996)Buy from Amazon now
Page count: 1,104
What it’s about: Set in a future North America, the plot ‘focuses’ on a halfway house for addicts, a tennis academy and an attack by separatists from Quebec, wrapped up with famously sprawling footnotes. Wallace was only 33 when he wrote it.
Why you should read it: There really is nothing like Infinite Jest and its themes have aged like a fine wine. The virality of pop culture, TV binge-watching... all of this is skewered in the book, in a story that wants to fight how entertainment has turned us all into mush - by making you work for your entertainment with a book that contains endless footnotes.
First line: I am seated in an office, surrounded by heads and bodies.
13. Zen & The Art Of Motorcycle Maintenance By Robert Pirsig (1974)Buy from Amazon now
Page count: 432
What it’s about: A man takes his son on a 17-day motorcycle journey. Along the way he discusses philosophy, his past and what is meant by ‘good’.
Why you should read it: Don't be put off by its title! It's not hawking Buddhism and doesn't really give much insight into motorbikes either. But what it does do is offer up philosophical questions that will/may get you questioning how you live.
First line: I can see by my watch, without taking my hand from the left grip of the cycle, that it is eight-thirty in the morning.
14. 2666 By Roberto Bolaño (2004)Buy from Amazon now
Page count: 912
What it’s about: Five sections with different characters and settings, all linked to a Mexican city where 300 young women have been murdered. It’s based on the real town of Ciudad Juarez, where thousands of women have been murdered or gone missing in the past 20 years.
Why you should read it: It's strange and maddening in places, but this is a novel for those who like to genre jump. It's got five sections that explore different genres, including thrillers, romantic fiction, detective fiction and much more.
First line: The first time that Jean-Claude Pelletier read Benno von Archimboldi was Christmas 1980, in Paris, when he was nineteen years old and studying German literature.
15. Little Dorrit By Charles Dickens (1857)Buy from Amazon now
Page count: 912
What it’s about: William Dorrit is being held in debtor’s prison Marshalsea, where Dickens’ father was once jailed. While Dorrit spends years locked up, his daughter — Little Dorrit — tries in vain to pay his debts. A satirical work that takes a swipe at HM Treasury and Britain’s burgeoning industrial workplace.
Why you should read it: There's no better description of Victorian London than in this book. And while you need to suspend disbelief when it comes to how the characters are all linked, the characters themselves are all beautifully realised.
First line: Thirty years ago, Marseilles lay burning in the sun, one day.