Challenging Books Everyone who is a self-proclaimed book-lover loves reading because books are fun! Most of us first fell in love with books through books like Matilda or the Goosebumps series, books that tell fun stories about magic and adventure. Wonderful as such books are, they’re not the only kind of fun to be had in literature. Sometimes the fun of a novel is the way it challenges you to think in new ways, or the way it plays with the very concept of what a book actually is. That’s not to say that the likes of Matilda wasn’t challenging for you as a kid; we all had to go through the growing pains of beefing up our vocabularies. But now that you’ve mastered your ABCs, and have maybe even taken on some of the big scary thousand-page challenges like War & Peace, you might be looking for a whole new challenge from your books. If that’s the case, then these are the books for you.Challenging Books Fair warning: these books are not for the casual reader. They’re the kind of make-your-brain-hurt, re-read-every-sentence-three-times, I-didn’t-know-words-could-do-that books that make most readers give up by Chapter 4. But, if you stick it out, you’re in for a real intellectual treat that’ll have you trying to force these tough tomes on all your friends. #1 Paradise by Toni Morrison Challenging Books This is easily Morrison’s most complicated novel, and also probably the most shocking, considering the first line is “They shoot the white girl first. With the rest they can take their time.” But beyond being a little traumatizing, it’s also pretty darn complex. There are so many time-shifts that you can hardly tell what the actual sequence of events is, and, not naming the characters until later in the book, it’s difficult to tell which character is which. On top of all that, you’d have to read the book every week for a lifetime before you could begin to see all of the meanings that exist under the surface of the novel. It’s incredibly rewarding to dig, though. #2 Finnegan’s Wake by James Joyce Challenging Books Finnegan’s Wake would easily make anyone’s list of most difficult books ever. It’s perhaps the king of all complex books. There’s nothing in this novel that looks anything like any other novel you’ve ever read. To embark on this book you’ll need dictionaries in various different languages, a very open mind, and an understanding that if you’ve only read this book once, then, ha!, you haven’t read it at all. #3 The Waves by Virginia Woolf Challenging Books So, there are six characters in this novel… and none of them actually interact or talk to each other. And, if you read it superficially, then it would seem like nothing even happens in the novel. But read it closely, and you’ll have to take frequent breaks to contemplate all the ideas Woolf is playing with. The Wavesis a series of six different internal monologues that don’t actually sound terribly different from each other. It’s a little bit of poetry, a little bit of prose, and a whole lot of weird. #4 Imaginations by William Carlos Williams Challenging Books Imaginations is actually a collection of what you might call a bunch of literary experiments by William Carlos Williams. One of the essays (or whatever you want to call it) is literary about the impossibility of writing. Other pieces are strange (but beautiful!) mixes of prose and poetry and other things. Honestly, it’s all just kind of a mess, but a pretty one. You could just open up to random pages and read a few lines and find yourself sighing blissfully without really even understanding what you just read. #5 The Chandelier by Clarice Lispector Challenging Books This one is so complex that you’ll have trouble finding a good translation of it (I had to read it in Spanish, but am totally including it here so that perhaps publishers will get the idea and make it more available. Cross your fingers!).Clarice Lispector’s novels are already pretty strange and nontraditional, but The Chandelier is the strangest and least traditional of them all. It reads sort of like what you’d imagine the inside of someone’s head sounds like, complete with non-sequiturs and broken-up bits of thoughts that would really only make sense to the person thinking them. If you can’t find the book in a language you know, don’t worry, Lispector’s other novels are equally strange and intellectually playful. Try Near to the Wild Heart! #6 Dhalgren by Samuel Delany Challenging Books Go ahead, just read the first page. Done yet? Confused yet? Yeah, the book’s protagonist is an amnesiac traveling to a fictional dystopian city called Bellona in a world where seriously weird things happen, like streets changing places and two moons randomly appearing in the sky. On top of that, the book sometimes seems a little plotless as you dive headfirst into the amnesiac hero’s stream of consciousness. If you manage to make it to the end of this bizarre book, you’ll not only be one of the few to do so, but you’ll either totally discouraged or blissfully bemused by what seems to make the novel something of a giant riddle. Good luck! #7 If On A Winter’s Night A Traveler by Italo Calvino Challenging Books If On A Winter’s Night A Traveler is about a reader who is trying to read a book called… If On A Winter’s Night A Traveler. Yep, it’s as much of a mind explosion as it sounds like. Parts of the book are in the rare second-person voice – that is, using “you,” which makes for a whole lot of philosophical confusion about who the book is talking about – you, the reader… or “you,” the guy in the book who is also the reader? Confused enough yet? #8 Hopscotch by Julio Cortazar Challenging Books This book comes with instructions from the author… should I continue? That’s never exactly a good sign unless it’s a choose-your-own-adventure novel. And, well, in a lot of ways this book is. You can read the novel in any number of ways or orders. It’s also got that tell-tale sign of a “difficult” novel – the stream-of-consciousness narrative style. All this combines to make a really fun reading experience that challenges you in ways you didn’t think a novel could. Side note: Grammar nerds, beware: Cortazar is also constantly breaking grammar rules in ways that might make you burst a neuron or two. #9 Tractatus Logico-Philosophicus by Ludwig Wittgenstein Challenging Books Not every complex book has to be a behemoth of a book. Tractatus Logico-Philosophicus is a measly hundred pages or so. However, the philosophical text takes on the entire idea of language and thought, asking, more or less, how language represents real things. I know, what am I even saying, right? Well, let’s just put it this way… it ain’t easy. And if that doesn’t convince you that it’s a tough text, remember that everybody’s favorite complicated author David Foster Wallace had lots of admiring and complicated things to say about the Tractatus.