Find out how to make hard reading material more accessible and more entertaining for all ages by using the right assistive technology software.

Hard books to read

Sometimes the best literary works make for the most difficult novels to read for both the average and experienced reader. Too much complexity can curb the audience’s enthusiasm and force them to flip to the last page just to find out the ending. The following books are great examples of revered stories packaged in a messy web of narrative styles.

The most difficult books to read in history

Ulysses by James Joyce

Published in 1922, “Ulysses” is one of the greatest literary masterpieces of all time. Although many students are required to provide a classroom analysis and commentary, “Ulysses” is also one of the tougher books to read, regardless of age. However, that doesn’t make the modernist Odyssey-inspired tale less exciting.

The entire action revolves around the events of June 16, 1904, in Dublin and follows three characters. James Joyce did a masterful job of drawing from Homer’s “Odyssey” and Odysseus’s adventures after the Trojan War.

Moby Dick by Herman Melville

“Moby Dick” is a classic adventure book filled with rich and often vulgar characters and a look at life at sea. The first-person perspective sees Ishmael as the narrator joining the whaling crew led by the mysterious captain Ahab.

The book follows the crew’s adventure as they go on a mission to kill a legendary white whale called Moby Dick. While Ishmael is in it for the new experience, Captain Ahab is on a quest for revenge and redemption. But the complex storytelling, character interactions, and motifs used in the book make it a tough read for younger readers.

Finnegans Wake by James Joyce

James Joyce is one of the most acclaimed writers of the 20th century, but he rarely published novels without a certain degree of complexity. Like “Ulysses,” “Finnegans Wake” is one of the author’s most challenging reads.

The experimental novel mixes real life and the dream world, following a philosophical notion that history is cyclical. The plot is one of the hardest to follow and can give modern science fiction movies like Inception a run for their money.

War and Peace by Leo Tolstoy

People study Leo Tolstoy’s classic books in classrooms worldwide in many languages. However, many of Tolstoy’s novels contain complex plots, multiple characters, and transcending character developments between the first and last pages.

War and Peace” explores Napoleon’s Russian invasion and how characters from different social backgrounds struggle with unique problems during hard times.

The Sound and the Fury by William Faulkner

William Faulkner’s “The Sound and the Fury” took two years to receive critical acclaim and required the author to publish two additional novels to make it happen. While it is one of the most impressive American literary works, the book’s plot isn’t easy to follow.

The book covers the aristocratic Compson family of Jefferson, Mississippi, for 30 years. However, the author splits the plot into four parts, uses different narrative styles, and mixes in stream-of-consciousness storytelling to present multiple perspectives. It’s as challenging as classic literature novels come.

Gravity’s Rainbow by Thomas Pynchon

Spy novels are often entertaining and favorites among all age groups, but “Gravity’s Rainbow” isn’t your average book. It’s one of the most challenging books that depict clandestine military organizations against a World War II backdrop.

As fun as it is to read about secret rocket research conducted by Nazis, multiple narrative threads, and complex characters, the book is a tough read due to its storytelling ambiguity.

Atlas Shrugged by Ayn Rand

“Atlas Shrugged” was 12 years in the making before its publication. Many consider the novel to be Ayn Rand’s ultimate masterpiece. However, the author’s view on human existence, answers to tough questions, and the fate of society is a narrative nightmare of sorts.

The novel is a riveting mystery story with plot turns and an unusual central victim for this genre – not a person but a man’s spirit. The novel is a riveting mystery story with plot turns and an unusual central victim in this genre – not a person but a man’s spirit.

One Hundred Years of Solitude by Gabriel Garcia Marquez

Gabriel Garcia Marquez’s novel follows multiple generations of the Buendias family, the founders of the isolated town of Macondo. The many narrative threads, characters, and impactful events make the book a difficult read.

And serving as the backdrop of everything the main characters experience is the town of Macondo. One of the main themes is its transformation from an isolated paradise to a town like all others with growing connections to the outside world.

House of Leaves by Mark Z. Danielewski

Mark Z. Danielewski published his first novel, “House of Leaves,” in 2000. Writing an experimental novel was a bold move, but it put the author in a select category of writers like Franz Kafka and Charles Dickens, who’ve written some of the best and most challenging books in history.

The narration combines multiple layers, relatable and broken characters, and stream-of-consciousness storytelling to bring together a complex plot. It’s a book that delves deeper into each layer as the story progresses and can give readers a headache as they try to untangle the main substance of the text.

Naked Lunch by William S. Burroughs

“Naked Lunch” is a 1959 English novel that follows a heroin user on a weird journey. The plot is hard to follow, given the fast action, fictional settings, and bizarre encounters and experimentations. Another aspect that makes the book challenging is the graphic depictions of substance abuse, violence, addiction, etc.

Add to that the off-beat spatial fluidity of life itself and existence, and “Naked Lunch” is a tough nut to crack.

Honorable mentions

A few other books came close to making this list, from short stories to multi-volume epic novels.

• Infinite Jest by David Foster Wallace
• To the Lighthouse by Virginia Woolf
• The Canterbury Tales by Geoffrey Chaucer
• In Search of Lost Time by Marcel Proust
• The Brothers Karamazov by Fyodor Dostoevsky
• The Silmarillion and the Lord of the Rings by J. R. R. Tolkien
• Blood Meridian by Cormac McCarthy
• Anna Karenina by Leo Tolstoy
• Heart of Darkness by Joseph Conrad

Fortunately, consuming demanding literary content is easier today than ever.

Speechify

Text to speech (TTS) software can help if you want to make reading or re-reading complex works easier. Speechify is a TTS reader that uses artificial intelligence to put written text into natural-sounding speech. It can take text from articles, illustrations, and scanned hardcopy documents and generate real-time audio narrations. It makes revisiting paragraphs and progressing at a desirable speed seamless for readers of all ages and interests.

Try Speechify to read and understand even the most difficult works like never before.