The most challenging books you will ever read

A list of brilliant, demanding books that will challenge you in various ways.

Be warned, within this list are some of the most challenging books you will ever read. Notorious for having too many pages, overly complicated language, or even being just so depressing that readers can’t carry on - these books are nevertheless celebrated as literary masterpieces. There might be times where you feel like giving up, or when you may not entirely understand what you are reading, but trust us when we say each of these books is well worth the effort. So . . . are you ready for a challenge?


by Hernan Diaz

Book cover for Trust

Trust is a book within a book that will demand your time and patience. In this Booker-longlisted novel about a Wall Street tycoon’s rise to power in 1920s New York, you’ll join the characters in disentangling fact from fiction. You’ll be taken on a quest for truth through multiple avenues of evidence: a work of fiction written about the tycoon and his wife, his own autobiography, a memoir written by an employee and the private diary of his late wife. As you slowly peel back each layer of the story, you’re challenged by your own judgement of whose version of events you can trust. Full of contradictions and manipulations, this is a work of metafiction that will have you trapped in its unpredictable pages.

Anna Karenina

by Leo Tolstoy

Book cover for Anna Karenina

Sitting at 1,136 pages, Anna Karenina is a novel of astonishing scope and grandeur, and if you're up for the challenge, Tolstoy's grand narrative and complex characters make for an intricate read. Anna, entangled in a consuming affair, battles societal norms in a restrictive Tsarist Russia. When Anna flees her stifling marriage and travels to Italy with dashing Count Vronsky, she finds herself isolated from all except the man she loves, and who loves her. But can they live by love alone? The richness of the text, its mastery of human emotions, and its vivid social panorama reward the dedicated reader. Anna Karenina is a masterpiece of realism and illuminated by irresistible characters from the grand master of Russian literature.

A Time Outside This Time

by Amitava Kumar

Book cover for A Time Outside This Time

A Time Outside This Time delves into the tumultuous landscape of memory, politics, and the blurring boundaries of truth in a digital age. With components like a globally impactful pandemic, a politically polarised climate, and the ceaseless churn of the news cycle, it presents a nuanced web to unpick. As reality and fabrication intertwine, this provocative novel might pose a demanding exploration. However, braving through its complexities rewards readers with a profound reflection of our post-truth era, making it a consequential read that resonates strikingly with current times.

A Little Life

by Hanya Yanagihara

Book cover for A Little Life

If you decide to pick up A Little Life, get ready to be emotionally challenged. At the centre of the story is Jude, a victim of unresolved trauma of which Hanya Yanagihara spares us no mercy in revealing. There are explicit moments of self-harm, addiction and abuse on Jude’s journey, and despite a sprinkling of compassion from his bittersweet friendships with Willem, Malcolm and JB, he never finds relief from this suffering. If you manage to appreciate this novel’s painful honesty and brutal display of human endurance, you’ll become emotionally invested in these characters who will remain in your heart forever. A strong contender for one of the most addictively depressing books you’ll ever read, prepare for a gut-punch on each of its 752 pages of beautifully explored misery.


by Don DeLillo

Book cover for Underworld

If you didn’t know much about American history in the eventful second half of the 20th century, you will after reading this. Spanning from the 1950s through to the 1990s in a non-linear fashion, Underworld is an 832 page panoramic vision of America. We weave in and out of a number of intertwined themes, including baseball, waste disposal, guns and the Cold War. But what also challenges us is its exhausting roster of disparate characters, as we dip into each of their respective lives while they search for meaning. Despite this being a beast of a book, it’ll reward the most patient of readers with its remarkable awe-inspiring story. We wouldn’t recommend enjoying it with a glass of wine though as you’ll already be drunk on Don DeLillo’s words.

To The Lighthouse

by Virginia Woolf

Book cover for To The Lighthouse

We all know how important the first page of a book is in drawing you in, but To the Lighthouse really makes you work for it. Written from the perspective of one’s inner voice, you are thrown straight into a blurred mesh of the Ramsay family’s thoughts and actions. Without the aid of frequent punctuation or consistent dialogue to carry you through, you’ll need to employ fierce levels of concentration to distinguish who’s inner monologue you’re in and what time of day it is. It's no easy task; if you look away for one moment, you’re lost. But there's a reason this book is regarded as one of the best novels ever written in the English language, and we promise that you will come away from this read having learnt much about the complexity of human relationships.

Paul Takes the Form of a Mortal Girl

by Andrea Lawlor

Book cover for Paul Takes the Form of a Mortal Girl

It’s time to rewrite all those intrinsic assumptions you have about gender, because Paul Takes the Form of a Mortal Girl will really challenge you to become open minded. Paul is a shapeshifter who can change his body whenever he likes, and he uses it to change into different gender identities. You’ll be charmed by this playful and provocative novel that follows Paul/Polly as they enter into different kinds of queer spaces. Prepare to be hypnotised by our hero/ine as he compulsively journeys through struggle and pleasure, challenging ideas of gender fluidity in a hilariously intimate manner. So if you’re looking for an adventurous escape from our world of categorisation, this will have you hooked.

Don Quixote

by Miguel de Cervantes

Book cover for Don Quixote

Have you tackled Europe's first 'modern' novel? Don Quixote, a profound yet hilariously tragic tale, charts the quixotic quests of an eccentric knight and his faithful squire in sixteenth-century Spain. With its intricate narrative over 1,000 pages long and satirical take on romantic tropes, Miguel de Cervantes' seminal work may be a demanding one. However, its timeless humor, inventive storytelling, and incisive social commentary ensure that the endeavor is highly rewarding, affirming Don Quixote as an enduring master of literature.


by Rian Hughes

Book cover for XX

The battle for your mind has already begun, figuratively, and quite literally. When AI expert Jack Fenwick tries to decode a mysterious signal, he finds a complex alien network from an interstellar civilization. What follows is a fictional battle to protect human minds, whilst in reality our minds as readers are in battle with the text on the page. Wrapping stories within stories, as well as featuring NASA transcripts, newspaper articles, artwork and Wikipedia pages, you could call this novel the Moby-Dick of sci-fi, but it’s even longer (1008 pages is no joke). But if you manage to decipher the narrative, you’ll enjoy a story of what might happen in the wake of the biggest scientific discovery in human history.

Finnegans Wake

by James Joyce

Book cover for Finnegans Wake

This novel begins in the middle of a sentence (that’s what you’re getting yourself into when you open this book.) It then ends in the middle of that same sentence, giving it a circular structure, with a whole load of dreamy, nonsensical language existing in between as a stream of consciousness. So come with the expectation that you won’t be making any sense of this famously incomprehensible novel. You could call the fantastic dream-language playful or you could call it baffling, pick your side! Don’t worry, there’ll be no shame if you admit you cannot understand this book, it's definitely a universal feeling. But you’ll still be left with a triumphant feeling at the end of it, having read perhaps the most challenging novel of all time.