5

If on a Winter's Night a Traveler -- Italo Calvino

If on a Winter's Night a Traveler is a book about a person reading a book called If on a Winter's Night a Traveler.

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If your hand instinctively made a jerking-off motion when you read that, well, that's not an uncommon reaction.

The book is told in interleaving chapters, with the odd-numbered chapters, about the person reading If on a Winter's Night a Traveler, told in second person. As in, "You are enjoying reading this book. You're not feeling annoyed at all by this and are definitely going to be recommending this book to your friends."

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"You also definitely aren't making a jerking-off motion with your hand right now."

4

"For Sale: Baby Shoes, Never Worn" -- Ernest Hemingway

"For Sale: Baby Shoes, Never Worn" is both the title and the entire text of a "novel" purportedly written by Ernest Hemingway. In the interest of accuracy, I should note that the authorship of the piece isn't wholly settled, but seeing as the story of Hemingway writing it to win a bar bet is so amusingly in sync with what we know about Hemingway's character, I highly recommend you not question it.

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"Who wants to bet that I can't drink this baby?"

3

A Void -- Georges Perec

A Void is a novel written using a stunt that I can barely contemplate. If someone asked me to try this with one of my columns, I'd say it was impossible and spit in their face.

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"Spell check, Jack? Inconceivable." -hork. horrrrrrrk. HORRRRRRRRRKKKKKKKKKKK-

2

Pale Fire -- Vladimir Nabokov

Nabokov might be better known for Lolita, his novel about the seduction of a 12-year-old girl that I'm not going to make too many jokes about.

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Not after Legal reviewed my column, anyways.

Pale Fire might be his better novel, though, constructed around, would you believe it, yet another insane structure. The book is laid out as a 999-line poem called Pale Fire, written by a fictional author, and presented alongside annotations written by a fictional editor and friend of the author. The plot of the novel is laid out in these annotations, which discuss both men's slightly nutty lives. Like the fact that they're haunted by a variety of ghosts, or that one of them might have been mistakenly killed by an assassin who was trying to kill the deposed king of a country called Zembla.

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That old saw.

What makes the plot so complicated is how non-linear it is, the details spelled out in the interplay between the poem and the annotations. With all those annotations pointing back and forth, it's often cited as being one of the first books written in hypertext.

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Which the world has since used for nothing but the highest-browed work, as evidenced by all the sites we have with [REDACTED BY CRACKED LEGAL] that are really just begging for it.

1

Finnegans Wake -- James Joyce

Finnegans Wake took James Joyce 17 years to write, and he was going to be damned if anyone would be able to read it in less time. Widely regarded to be among the most difficult books in the English language, Finnegans Wake tells the story of... something. That's about all anyone can say, really.

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"A word, a word, a word. Another one. Yes, there's definitely something going on here, word-wise."

To make any sense of the work involves unpacking it sentence by sentence, subjecting every word to a brutally intensive analysis, collecting all the various meanings that fall out of this process, and reassembling them into something that actually resembles a coherent thought; reading it is a serious fucking operation.

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No shit.

The whole book is written in stream-of-consciousness, dream-logic gibberish, in languages that don't actually exist. Joyce invented his own completely bonkers language that was kind of English but also not, sort of as if he'd taken English and lightly pulsed it in a food processor before he started writing with it. The book has no plot that deserves the name, although trying to analyze it for a plot may be missing the point entirely. There are main characters of a sort, but they're a little hard to pin down, given the fact that they are given hundreds, even thousands of names within the text.

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"Heh heh heh heh hehhhhhhehhehehe."

In short, it's basically unlike anything that's ever been written. If we're being generous, we can call this the work of a man trying to reinvent the very concepts of a novel, language, and possibly even concepts themselves.

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"No, I did it to fuck with people."

Ahh, well there you go. OK, I take everything back. Fuck books.

Chris Bucholz is a Cracked columnist and does not want you to take that literally. Join him on Facebook or Twitter.