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10 Works of Literature That Were Really Hard to Write

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Instead of judging works of literature based on their artistic merit, we’ve decided to rank them by degree of difficulty. These 10 authors may not be Shakespeare, but they sure had vaulting ambitions.

1. The Story That Will Never Be an e-Book
Gadsby by Ernest Vincent Wright

Some might call Gadsby a “love” story. But Ernest Vincent Wright wouldn’t have used that word. Instead, he described his novel as a story of “strong liking” and “throbbing palpitation.” That’s because in 1939, Wright gave himself one restriction: He promised to write Gadsby without using the letter E.

Wright wanted to prove that a great author could work around such a restriction and still tell a gripping story. To prevent any stray Es from entering the text, he tied down his typewriter’s E key, and then put his expansive vocabulary to the test. The result is an astounding feat of verbal gymnastics. While vividly describing a wedding scene, Wright manages to avoid the words “bride,” “ceremony,” and even “wedding” (he calls it “a grand church ritual”). To explain away the verbosity of the language, he uses a narrator whose poor command of English and circumlocution even irritates the story’s other characters.

When the book was announced, one skeptic attacked Wright in a letter, claiming that the feat was impossible. “All right,” replied Wright in the book’s intro, “the impossible has been accomplished.” Sadly, Wright didn’t live long enough to revel in Gadsby’s critical acclaim. He died the year the book was published.

2. The Tale Told in the Blink of an Eye
The Diving Bell and the Butterfly by Jean-Dominique Bauby

Many authors have struggled through illness and injury to write their masterpieces, but none more so than Jean-Dominique Bauby, editor-in-chief of French fashion magazine Elle.

In 1995, at the age of 43, Bauby suffered a major stroke and slipped into a coma. He regained consciousness two days later, but his entire body—with the exception of his left eyelid—was paralyzed.

Still, Bauby was determined to write. Using only his lucid mind and one eye, he began working on his memoir, The Diving Bell and the Butterfly. Each night, he’d lie awake editing and re-editing the story in his mind, memorizing every paragraph as he hoped to relay it. By day, his transcriber would recite the alphabet to him over and over. When she reached a letter Bauby desired, he’d wink. Each word took about two minutes to produce, and during the course of a year, Bauby managed to tell his story of life in paralysis. His moving and often funny prose won critical acclaim, and The Diving Bell and the Butterfly became a bestseller throughout Europe. Sadly, Bauby died of pneumonia in 1997, soon after the first edition was published in France. He missed not only the English translation, but also the award-winning film adaptation released in 2007.

3. The Poetry of Speed
Transcendence-Perfection by Sri Chinmoy

Before his death in 2007, Indian spiritual master Sri Chinmoy wrote at least 1,000 books, 20,000 songs, and 115,000 poems. Some he penned in his mother tongue, Bengali, and some in his second language, English. His poems won numerous awards and inspired countless writers and musicians. And while Sri Chinmoy was clearly a fast writer, he was never as quick as on November 1, 1975, when he wrote Transcendence-Perfection, a collection of 843 poems—all written in 24 hours.

How was Sri Chinmoy so prolific? He believed the key was meditation. As he once explained, “The outer mind is like the surface of the sea. On the surface, the sea is full of waves and surges ... But when we dive deep below, the same sea is all peace, calmness and quiet, and there we find the source of creativity.”

4. History’s Greatest Sonnet
"Washington Crossing the Delaware" by David Shulman

Etymologist David Shulman was a true lover of words. One of the most prolific contributors to the Oxford English Dictionary, Shulman tracked down the roots of Americanisms for more than 70 years. But those weren’t Shulman’s only contributions to the world. During World War II, he served in the army and used his language skills to crack Japanese codes. His most astonishing feat as a wordsmith, however, occurred in 1936, when he composed the sonnet "Washington Crossing the Delaware."

What makes the poem so remarkable is that every one of Shulman’s 14 lines is an anagram of the title. What’s more, the lines are rhyming couplets, and they tell a story, more or less. Here’s an excerpt:

A hard, howling, tossing water scene.
Strong tide was washing hero clean.
“How cold!” Weather stings as in anger.
O Silent night shows war ace danger!

As poetry, it isn’t exactly Walt Whitman. But then, Whitman was never this good with anagrams.

5. The Story of Youth
The Young Visiters, by Daisy Ashford


Daisy Ashford’s novella about Victorian society is considered something of a classic. First published in 1919, the work is still in print and has been turned into a movie. But if that doesn’t sound remarkable, consider that Ashford was only 9 years old when she wrote it.

To preserve the authenticity of the story, publishers decided to leave in Ashford’s plentiful grammar mistakes and spelling errors (the title, for example). They also added a foreword by Peter Pan author J.M. Barrie to assure readers that this was no hoax. Barrie reminded people that the novel was indeed written by a little girl, who was “hauled off to bed every evening at six.”

6. The Most Visionary Story Ever Told
Futility by Morgan Robertson

Occasionally, literature is prophetic. H.G. Wells’ stories, for instance, predicted video recordings, portable television, aerial bombings, and a Second World War starting in 1940 (only one year late). And a 1941 comic book written by Gil Fox described the bombing of Pearl Harbor in surprising detail, precisely one month before it happened.

But perhaps the most meticulously prophetic work of literature is Morgan Robertson’s short and poorly written novel, Futility. In it, Robertson describes the maiden voyage of a British luxury liner called the Titan, which claims to be unsinkable, but sinks anyway after hitting an iceberg. Nearly every detail resembles the story of the Titanic. Of course, nobody thought about that when Futility was released in 1898, a full 14 years before the Titanic set sail.

Futility wasn’t Robertson’s only prescient piece of literature. In 1912, three years before his death, he wrote Beyond the Spectrum. Much like Gil Fox’s tale, Robertson’s story predicted a Japanese sneak attack on an American fleet in Hawaii, and the resulting war between the two countries.

7. Writing by Ear
Anguish Languish by Howard L. Chace

Sinker sucker socks pants, apocryphal awry. If those words don’t make sense together, try saying them out loud: “Sing a song of sixpence, a pocketful of rye.” Now imagine a whole book written like this, and you’ve got Howard L. Chace’s 1940 collection of nursery rhymes and fairy tales, Anguish Languish. The work contains classics such as Marry Hatter Ladle Limb and Ladle Rat Rotten Hut, which begins with the immortal line, “Wants pawn term, dare worsted ladle gull hoe lift wetter murder inner ladle cordage.” Although Anguish Languish is playful, there was also a serious side to it. As a French professor, Chace used the stories to illustrate that, in spoken English, intonation is almost as important to the meaning as the words themselves.

8. James Joyce’s Deaf Translation Jam
Finnegans Wake by James Joyce

James Joyce wrote his final novel, Finnegans Wake, during a 17-year period in Paris, finishing the work just two years before his death in 1941. During that time, Joyce was nearly blind, so he dictated his stream-of-consciousness prose to his friend, Samuel Beckett. That led to some unexpected results. For example, during one session, Joyce heard a knock at the door, which was too quiet for Beckett to perceive. Joyce yelled to the visitor, “Come in!” so Beckett added “Come in!” to the manuscript. When Beckett later read the passage back to Joyce, the author decided that he liked it better that way.

After several such sessions, Finnegans Wake became one of the most impenetrable works of English literature. But the experience didn’t just affect Joyce’s novel; it seemed to have a lasting effect on Beckett’s writing, as well. Beckett would go on to become a leading playwright in the Theatre of the Absurd, where his characters often spent their entire time on stage sitting in the middle of nowhere, hoping that someone would hear their voice.

9. Six Powerful Words
“Baby Shoes”

While the following anecdote may be apocryphal, whoever did write “Baby Shoes” has forced writers forever after to consider the economy of words. Today, the work has inspired countless six-word memoir and story competitions, proving that a story’s brevity is no limit to its power.

According to legend, while having lunch at New York City’s famous Algonquin Round Table, Ernest Hemingway bragged that he could write a captivating tale—complete with beginning, middle, and end—in only six words. His fellow writers refused to believe it, each betting $10 that he couldn’t do it. Hemingway quickly scribbled six words down on a napkin and passed it around. As each writer read the napkin, they conceded he’d won. Those six words? “For sale. Baby shoes. Never worn.”

10. The Art of Writing by Committee
The President’s Mystery Story by Franklin Roosevelt and seven other novelists

Many American presidents have written books, but only Franklin Roosevelt has contributed to a mystery novel. At a White House dinner in 1935, Roosevelt pitched his story idea to author Fulton Oursler. Roosevelt’s tale started like this: A man named Jim Blake is trapped in a stale marriage and a boring job. He dreams of running off with $5 million and starting over with a new identity.

Unfortunately, the President hadn’t worked out one major plot point: How does a man with $5 million disappear without being traced?

To solve the problem, Oursler formed a committee of five other top mystery writers: Rupert Hughes, Samuel Hopkins Adams, Rita Weiman, S. S. Van Dine, and John Erskine. Each author wrote a chapter and ended it with Jim Blake in a terrible situation, which the next author was left to resolve. Despite being the work of a Washington committee, the end result was surprisingly successful. The President’s Mystery Story was serialized in a magazine, published as a book, and even turned into a movie in 1936.

Yet, the writers never came up with a solution to Roosevelt’s original problem. That didn’t happen until 1967, when Erle Stanley Gardner wrote a final chapter to a new edition of the book. In it, the secret to Jim Blake’s mysterious disappearance is discovered by Gardner’s most famous character, Perry Mason.

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10 Things You Might Not Know About J.D. Salinger
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For the past few decades, if any artist has been celebrated for a slim body of work and subsequently disappeared from public view, they’ve invited comparison to Jerome David (J.D.) Salinger. The author (1919-2010) published only one novel in his lifetime, 1951’s The Catcher in the Rye—but what a novel it was. A bildungsroman (coming of age) story about an aimless young man named Holden Caulfield on a mission to find himself after being expelled from a private school, The Catcher in the Rye ushered in a new era of philosophical literature, becoming a staple of classrooms across the country.

A new film about Salinger, Danny Strong's Rebel in the Rye, is once again stirring interest in the reclusive artist. If you’re a little light on Salinger trivia, check out some facts about his war experiences, his disappointing fling with Hollywood, and one curious choice of beverage.

1. HE WORKED ON THE CATCHER IN THE RYE WHILE FIGHTING IN WORLD WAR II.

Salinger was a restless student, attending New York University, Ursinus College, and Columbia University in succession. While taking night classes at the latter, he met Whit Burnett, a professor who also edited Story magazine. Sensing Salinger’s talent for language, Burnett encouraged him to pursue his fiction. When World War II broke out, Salinger was drafted into the Army. During his service from 1942 to 1944, he worked on chapters for what would later become The Catcher in the Rye, keeping pages on his person even when marching into battle.

2. HE HAD A NERVOUS BREAKDOWN.

Following his service, Salinger experienced what would later be labeled post-traumatic stress disorder: He was hospitalized after suffering a nervous breakdown in Nuremburg in 1945 after seeing some very bloody battles on D-Day and in Luxembourg. Writing to Ernest Hemingway, whom he had met while the latter was a war correspondent for Collier’s, he said his despondent state had been constant and he sought out help “before it got out of hand.”

3. HE REFUSED TO BE REWRITTEN.

Settling back in New York after the war, Salinger continued to write, contributing short stories to The New Yorker and other outlets before finishing The Catcher in the Rye. In literary circles, his name was already becoming known for insisting that editors not change a single word of his writing. When publisher Harcourt Brace agreed to publish The Catcher in the Rye, Salinger broke away from the deal after they insisted on rewrites. The untouched book was eventually released by Little, Brown and Company.

4. THE NEW YORKER DECLINED TO PRINT A CATCHER IN THE RYE EXCERPT.

A supply of Catcher in the Rye copies by author J.D. Salinger
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Despite having published stories in The New Yorker previously, Salinger was dismayed to discover that the magazine wasn’t very supportive of his novel debut. Getting an advance copy of the book in the hopes they would run an excerpt, editors said the book's characters were “unbelievable” and declined to run any of it.

5. HE DID GIVE ONE INTERVIEW ... TO A HIGH SCHOOL STUDENT.

Early on, it became apparent that Salinger wasn’t going to embrace whatever celebrity The Catcher in the Rye brought to his doorstep. He insisted that Little, Brown not run an author’s photo on the book’s dust jacket and turned down any opportunities to publicize it—with one exception. After moving to New Hampshire, Salinger agreed to give an interview to a local high school paper, The Claremont Daily Eagle. Salinger was later dismayed to find out an editor wound up putting it on the front page of the local paper. Annoyed and feeling betrayed, he put up a six-foot, six-inch tall fence around his property, further walling himself off from prying eyes.

6. HE DID WIND UP SELLING A MOVIE IDEA.

Although his most celebrated work has been kept offscreen, Salinger did have a brief courtship with Hollywood. In 1948, producer Darryl Zanuck purchased the rights to one of his short stories, “Uncle Wiggily in Connecticut.” Released as My Foolish Heart in 1949, it earned actress Susan Hayward an Oscar nomination (plus a second one for Best Original Song). Salinger reportedly hated it.

7. HE SUED HIS BIOGRAPHER.

Choosing a difficult subject to profile, author Ian Hamilton insisted on pursuing a biography of Salinger in the 1980s. Salinger was so peeved he sued Hamilton to prevent him from using excerpts of unpublished letters. A Supreme Court ruling gave him a victory, barring Hamilton from using the passages. Hamilton later wrote a book, 1988's In Search of J.D. Salinger, an account of his own legal dealings with Salinger.

8. HE PROBABLY DRANK HIS OWN PEE.

By Time Inc., illustration by Robert Vickrey. Time Magazine Archive - National Portrait Gallery Collection, Public Domain, Wikimedia Commons

Salinger’s reclusive habits made him easy prey for a litany of rumors, but some of his more intriguing habits were disclosed by his daughter, Margaret, in a memoir that described her father as speaking in tongues and occasionally sipping his own urine. That practice, called urophagia, is said to have health benefits, although no reputable studies have been able to demonstrate as much.

9. HE ALWAYS LOATHED THE IDEA OF A CATCHER IN THE RYE MOVIE.

With its persistent interior monologues, The Catcher in the Rye might be almost unfilmable—but that hasn’t stopped directors as revered as Billy Wilder and Steven Spielberg from trying. Throughout his life, Salinger famously rebuffed any attempt to purchase the rights to make a film from his book, but did leave open a small possibility that it could possibly happen after he died. “It pleasures me to no end, though,” he once wrote, “to know that I won’t have to see the results of the transaction.” (The Salinger estate has yet to disclose whether they would seek to prevent an adaptation.)

10. A CARTOONIST WON A RESIDENCY AT HIS HOUSE.

In late 2016, the Cornish Center for Cartoon Studies Residency Fellowship accepted applications for cartoonists who wished to live in a one-bedroom apartment above the garage of Salinger’s former residence in Cornish, New Hampshire. The fellowship was granted so the winner could have a place to focus and produce “exceptional work.” The CCS repeated the offer this year, with a guest due to move in on October 16. Harry Bliss, a cartoonist for The New Yorker, is the current owner of the property.

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How the Rise of Paperback Books Turned To Kill a Mockingbird Into a Literary Classic
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If you went to middle or high school in the U.S. in the last few decades, chances are you’ve read To Kill a Mockingbird, Harper Lee's now-classic novel (which was adapted into a now-classic film) about racial injustice in the South. Even if you grew up far-removed from Jim Crow laws, you probably still understand its significance; in 2006, British librarians voted it the one book every adult should read before they die. And yet the novel, while considered an instant success, wasn’t always destined for its immense fame, as we learned from the Vox video series Overrated. In fact, its status in the American literary canon has a lot to do with the format in which it was printed.

To Kill a Mockingbird came out in paperback at a time when literary houses were just starting to invest in the format. After its publication in 1960, To Kill a Mockingbird was reviewed favorably in The New York Times, but it wasn’t the bestselling novel that year. It was the evolution of paperbacks that helped put it into more hands.

Prior to the 1960s, paperbacks were often kind of trashy, and when literary novels were published in the format, they still featured what Vox calls “sexy covers,” like a softcover edition of The Great Gatsby that featured a shirtless Jay Gatsby on the cover. According to a 1961 article in The New York Times, back in the 1950s, paperbacks were described as “a showcase for the ‘three S’s—sex, sadism, and the smoking gun.’” But then, paperbacks came to schools.

The mass-market paperback for To Kill a Mockingbird came out in 1962. It was cheap, but had stellar credentials, which appealed to teachers. It was a popular, well-reviewed book that earned Lee the Pulitzer Prize. Suddenly, it was in virtually every school and, even half a century later, it still is.

Learn the whole story in the video below from Vox.

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