2026 Reading Challenge

Listopia > Difficult Book Lists

Finnegans Wake by James JoyceUlysses by James JoycePhenomenology of Spirit by Georg Wilhelm Friedrich HegelGravity’s Rainbow by Thomas PynchonCritique of Pure Reason by Immanuel Kant
REALLY, REALLY DIFFICULT BOOKS
260 books — 363 voters
The Lightning Thief by Rick RiordanPeter Nimble and His Fantastic Eyes by Jonathan AuxierHarry Potter and the Sorcerer's Stone by J.K. RowlingThe Strange Case of Origami Yoda by Tom AnglebergerHarry Potter Series Box Set by J.K. Rowling
After Wimpy Kid
191 books — 158 voters

Moby Dick by Herman MelvilleGravity's Rainbow by Thomas PynchonInfinite Jest by David Foster WallaceWar and Peace by Leo TolstoyHeart of Darkness by Joseph Conrad
Flavorwire's 50 Incredibly Tough Books for Extreme Readers
50 books — 105 voters
Ulysses by James JoyceHeart of Darkness by Joseph ConradHamlet by William ShakespeareThe Scarlet Letter by Nathaniel HawthorneWuthering Heights by Emily Brontë
Difficult Reading
102 books — 101 voters

September Ends by Hunter S. JonesSame Old Truths by Delora DennisThe Daughter-in-law Syndrome by Stevie TurnerTorn by Billy Wood-SmithAn Interrupted Love Story by Billy Wood-Smith
Difficult relationships/ Modern love stories
45 books — 58 voters
Choosing Theo by Victoria AvelineGrim by M.K. EidemStolen by an Alien by Amanda MiloLord of the Storm by Justine DavisEyes of Silver, Eyes of Gold by Ellen O'Connell
Hero Considered Less Than
95 books — 39 voters

Phenomenology of Spirit by Georg Wilhelm Friedrich HegelTo the Lighthouse by Virginia WoolfThe Waves by Virginia WoolfUlysses by James JoyceCritique of Pure Reason by Immanuel Kant
The Millions' World's Most Difficult Books
21 books — 17 voters
The Midnight Library by Matt HaigFoods That Fight Pain by Neal D. BarnardElphie by Gregory MaguireBlack Woods Blue Sky by Eowyn IveyA Visit from the Goon Squad by Jennifer Egan
Abandoned in 2025
82 books — 14 voters

Finnegans Wake by James JoyceI Seem to Be a Verb by R. Buckminster FullerUlysses by James JoyceRiddley Walker by Russell HobanA Clockwork Orange by Anthony Burgess
Books Bordering on Unintelligible
12 books — 13 voters
Domination & Submission by Michael MakaiWhen I Met Elena by Desiree SpanMen As Friends by Irwin EpsteinThe Jewish Neighbor by A.M. KhalifaThe Tiger's Wedding by James Dante
Difficult Interethnic/Intercultural Romantic Relationships
5 books — 10 voters

Don't Close Your Eyes by Lynessa JamesComplicated Moonlight by Lynessa LayneMad Love by Lynessa LaynePride and Prejudice by Jane AustenJane Eyre by Charlotte Brontë
Best "Hard to get Ladies and Fellows" books
8 books — 9 voters
Never Go With Your Gut by Gleb TsipurskyThe Handmaid’s Tale by Margaret AtwoodPride and Prejudice by Jane AustenOn the Road by Jack KerouacThe Da Vinci Code by Dan Brown
List of Betterment
44 books — 8 voters

The Illuminatus! Trilogy by Robert SheaFinnegans Wake by James JoyceTropic of Cancer by Henry MillerDas Kapital by Karl MarxNew Science by Giambattista Vico
Most difficult books I've come across
6 books — 3 voters
Ulysses by James JoyceGravity’s Rainbow by Thomas PynchonThe Devil to Pay in the Backlands by João Guimarães RosaPale Fire by Vladimir NabokovThe Brothers Karamazov by Fyodor Dostoevsky
Libri Akro
33 books — 1 voter

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