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You may have noticed that some of the most celebrated and iconic works of literature are by no means easy reads.
In fact, they often push the boundaries of structure, narrative conventions, and deal with difficult subject matters.
Every bookworm you speak to will admit to trying to tackle a challenging classic, only to put it down because they couldn’t wrap their heads around it!
While we totally sympathize with wanting to trade in a tough classic for something simpler (challenging isn’t always synonymous with good, after all), the truth is, a lot of these complex classics are worth pushing through.
But which notoriously difficult books are worth your time? Well, we’ve rounded up six famously complex must-reads for you to try!
Finnegan’s Wake by James Joyce
This head-scratcher of a novel is probably one of the first that comes to mind when you think of challenging works of literature.
James Joyce wrote Finnegan’s Wake over a twenty-year period, and when you read this book it’s easy to see why.
A big part of what makes this book so complex is its use of stream of consciousness, which is unwieldy to say the least and refuses to follow any firm structure.
But soldiering on with this novel is totally worth it. It is widely considered a masterpiece, smashing up the rules of storytelling and what readers can expect from a novel.
Infinite Jest by David Foster Wallace
Infinite Jest is a novel that is both funny and exuberant, as well as deeply philosophical.
It takes place in a future world, where the United States, Mexico and Canada have formed a giant superstate, the Organizations of North American Nations, or the O.N.A.N. But the novel centers on the Incandenza family, a dysfunctional and fascinating group of people.
The main theme of the novel is the human desire to be entertained, even when that is at the expense of others, and when it threatens genuine connections with those around us, and our inner selves.
Infinite Jest isn’t just a profound novel that is sure to get you thinking, but it’s incredibly entertaining too.
What makes this such a challenging read, however, is the book’s length (at over a thousand pages), the unconventional narrative structure, and the footnotes and endnotes that fill each page.
Still, Infinite Jest has sold over a million copies all over the world and is one of the most celebrated novels of the 20th century.
War And Peace by Leo Tolstoy
Speaking of lengthy novels, War And Peace is the undisputed king of them all, as well as being an iconic example of a literary epic. Exceeding 1,000 pages, reading War And Peace is a challenge not to be taken lightly.
Yes, the Russian names may be hard to keep track of at first, and some passages feel like philosophical tangents rather than a traditional narrative, but once you get used to all that, it’s a novel you won’t want to put down.
War And Peace follows five aristocratic families in Tsarist Russia during the French invasion, and features some of the most memorable characters in 19th-century literature.
Like many classic works published in this time, War And Peace was originally a series rather than a complete work, and if you want to make your reading experience more manageable, you can still buy the book in shorter installments today.
Moby Dick by Herman Melville
Arguably the most famous addition to this list, Moby Dick is considered one of the most difficult-to-read American novels.
Herman Melville’s most famous novel follows a ship captain obsessed with hunting down a white whale across a large and violent ocean.
This may seem like a rather straightforward premise, but this adventure on the high seas includes sprawling encyclopedic-style entries regarding whales, both their anatomy and the history of hunting them.
You can also find some editions of Moby Dick with illustrations, maps, and further notes, as well as a glossary so you can translate some of the more complex and obscure nautical terms.
It’s unlikely you can finish Moby Dick in a couple of days. In fact, we believe it’s best enjoyed at a leisurely pace, so you can savor every rich detail.
One Hundred Years Of Solitude By Gabriel Garcia Marquez
One of the most famous Latin American novels, One Hundred Years of Solitude is a landmark novel by Colombian author Gabriel Garcia Marquez.
The novel spans generations, chronicling the rocky lives of the Buendia family, founders of the fictional town of Macondo.
Over a hundred years, the family becomes entangled in some of the most poignant and significant events in Colombian history.
Some have described this novel as the quintessential fairy tale for adults, and also one of the most masterful examples of magical realism.
But don’t be fooled, this novel is not an easy read. The intertwined generations make the narrative tough to follow at times, especially when a lot of characters share the same name.
However, the overall experience of reading One Hundred Years Of Solitude makes its more challenging aspects well worth it. It is truly one of the most spell-binding and engaging novels of all time.
The Unconsoled by Kazuo Ishiguro
Undoubtedly one of the most challenging novels by the acclaimed author Kazuo Ishiguro, The Unconsoled is bursting with bizarre metaphors and narratives that are transcendental.
The Unconsoled follows a famous pianist who travels to a city in Central Europe to play a concert he has no recollection of agreeing to play.
In fact, where he even is exactly is a mystery to him. But leading up to his performance, he falls into a dreamlike state and quickly loses grip on reality.
What makes this a challenging read is its complex themes and plot that defies logic. In fact, when it was originally published in 1995, critics unfavorably deemed it ‘baffling’ and ‘indecipherable.’
But like most challenging literary works, the tides of criticism soon shifted, and now The Unconsoled is considered one of Ishiguro’s most engaging works, and one of the most provocative novels of the 20th century.
Final Thoughts
If you want to take on a challenging literary classic but don’t know where to start, we hope our article has helped you out! These novels may take a while to get into, but once you sink your teeth in, you’ll be glad you did as these rich, groundbreaking and provocative works are classics for a reason.
I first had the idea for Seeking A Good Book when I was in college and everyone would come to me for book recommendations. More often than not, everyone I recommended a book to would always come back with a glowing review of it.
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