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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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5 Things You Should Know About Chinua Achebe
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Often referred to as the “father of African literature,” author Chinua Achebe was born in Ogidi, Nigeria on this day in 1930. Though he passed away in 2013, Google is celebrating what would be his 87th birthday with a Google Doodle. Here are five things you should know about the award-winning writer.

1. HE HAD PLANNED TO BE A DOCTOR.

Though he was always an avid reader and began learning English at the age of eight, Chinua Achebe hadn’t always planned to become a beacon of the literary world. After studying at Nigeria’s prestigious Government College (poet Christopher Okigbo was one of his classmates), Achebe earned a scholarship to study medicine at University College in lbadan. One year into the program he realized that writing was his true calling and switched majors, which meant giving up his scholarship. With financial help from his brother, Achebe was able to complete his studies.

2. JOYCE CARY’S MISTER JOHNSON INSPIRED HIM TO WRITE, BUT NOT IN THE WAY YOU MIGHT THINK.

While storytelling had long been a part of Achebe’s Igbo upbringing in Nigeria, that was only part of what inspired him to write. While in college, he read Mister Johnson, Irish writer Joyce Cary’s tragicomic novel about a young Nigerian clerk whose happy-go-lucky demeanor infects everyone around him. While TIME Magazine declared it the “best book ever written about Africa,” Achebe disagreed.

“My problem with Joyce Cary’s book was not simply his infuriating principal character, Johnson,” Achebe wrote in Home and Exile. “More importantly, there is a certain undertow of uncharitableness just below the surface on which his narrative moves and from where, at the slightest chance, a contagion of distaste, hatred, and mockery breaks through to poison his tale.” The book led Achebe to realize that “there is such a thing as absolute power over narrative,” and he was inspired to take control of it to tell a more realistic tale of his home.

3. HE DIDN’T THINK THAT WRITING COULD BE TAUGHT.

Though he studied writing, Achebe wasn’t all too sure that he learned much about the art in college. In an interview with The Paris Review, he recalled how the best piece of advice he had ever gotten was from one of his professors, James Welch, who told him, “We may not be able to teach you what you need or what you want. We can only teach you what we know.”

I thought that was wonderful. That was really the best education I had. I didn’t learn anything there that I really needed, except this kind of attitude. I have had to go out on my own. The English department was a very good example of what I mean. The people there would have laughed at the idea that any of us would become a writer. That didn’t really cross their minds. I remember on one occasion a departmental prize was offered. They put up a notice—write a short story over the long vacation for the departmental prize. I’d never written a short story before, but when I got home, I thought, Well, why not. So I wrote one and submitted it. Months passed; then finally one day there was a notice on the board announcing the result. It said that no prize was awarded because no entry was up to the standard. They named me, said that my story deserved mention. Ibadan in those days was not a dance you danced with snuff in one palm. It was a dance you danced with all your body. So when Ibadan said you deserved mention, that was very high praise.

I went to the lecturer who had organized the prize and said, You said my story wasn’t really good enough but it was interesting. Now what was wrong with it? She said, Well, it’s the form. It’s the wrong form. So I said, Ah, can you tell me about this? She said, Yes, but not now. I’m going to play tennis; we’ll talk about it. Remind me later, and I’ll tell you. This went on for a whole term. Every day when I saw her, I’d say, Can we talk about form? She’d say, No, not now. We’ll talk about it later. Then at the very end she saw me and said, You know, I looked at your story again and actually there’s nothing wrong with it. So that was it! That was all I learned from the English department about writing short stories. You really have to go out on your own and do it.

4. HE WAS WARY OF MACHINES.

Though typewriters, followed by computers, were ubiquitous, Achebe preferred a “very primitive” approach. “I write with a pen,” he told The Paris Review. “A pen on paper is the ideal way for me. I am not really very comfortable with machines; I never learned to type very well. Whenever I try to do anything on a typewriter, it’s like having this machine between me and the words; what comes out is not quite what would come out if I were scribbling. For one thing, I don’t like to see mistakes on the typewriter. I like a perfect script. On the typewriter I will sometimes leave a phrase that is not right, not what I want, simply because to change it would be a bit messy. So when I look at all this … I am a preindustrial man.”

5. HIS DEBUT NOVEL REMAINS ONE OF THE MOST TAUGHT PIECES OF AFRICAN LITERATURE.

Achebe’s status as the “father of African literature” is no joke, and it’s largely due to his debut novel, Things Fall Apart. Published in 1958, the book—which follows the life of Okonkwo, an Igbo leader and wrestling champion—has gone on to sell more than 10 million copies and has been translated into 50 different languages. Even today, nearly 60 years after its original publication, it remains one of the most taught and dissected novels about Africa.

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13 Fascinating Facts About Kurt Vonnegut
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Best known as the eccentric author of Slaughterhouse-Five and Cat’s Cradle, Kurt Vonnegut filled his novels, plays, and short stories with irreverence, satire, and wry wit. He wrote about dystopian societies, disillusionment with war, and skepticism, particularly connecting with millions of readers in the 1960s counterculture. To celebrate what would have been Vonnegut’s 95th birthday, we compiled a list of facts about the beloved science fiction writer.

1. HE MET HIS FIRST WIFE IN KINDERGARTEN.

Born in Indianapolis, Indiana in 1922, Vonnegut met his future wife, Jane, in kindergarten. Although they dated as teenagers in high school, their relationship paused when Vonnegut went to Cornell University, dropped out to serve in World War II, and became a prisoner of war in Germany. After returning to the U.S., he married Jane in 1945. The couple had six children—three biological and three adopted—but divorced in 1971.

2. HIS MOTHER COMMITTED SUICIDE ON MOTHER'S DAY.

When Vonnegut was born, his parents were well-off. Kurt Sr., his father, was an architect and Edith, his mother, was independently wealthy from the brewery that her family owned. But due to Prohibition and the Great Depression, the family struggled to make ends meet, sold their home, and switched their son to a public school. Edith, who suffered from mental illness, became addicted to alcohol and prescription pills. In 1944, when Vonnegut came home from military training to celebrate Mother’s Day, he found Edith dead. She had committed suicide by overdosing on sleeping pills, and the 21-year-old Vonnegut soon went to Germany to fight in World War II. In an interview with The Paris Review, Vonnegut remembered his mother as being highly intelligent, cultivated, and a good writer. "I only wish she’d lived to see [my writing career]. I only wish she’d lived to see all her grandchildren," he said.

3. HE TURNED HIS PRISONER OF WAR EXPERIENCE INTO A BESTSELLING BOOK.


By United States Army [Public domain], via Wikimedia Commons

Because Vonnegut was flunking his classes at Cornell, he decided to drop out and join the army to fight in World War II. During the Battle of the Bulge, in 1944, German forces captured him, along with other American prisoners of war, in Dresden. Forced to work long hours in a malt-syrup factory, he slept in a subterranean slaughterhouse. In a letter he later wrote to his family, Vonnegut described the unsanitary conditions, sadistic guards, and measly food rations. After surviving the February 1945 Allied bombing of Dresden, in which tens of thousands of people were killed, Vonnegut was forced by his captors to remove jewelry from the corpses before cremating them. "One hundred thirty thousand corpses were hidden underground. It was a terribly elaborate Easter-egg hunt," he said in his Paris Review interview.

Later in 1945, Vonnegut got frostbite and was discharged from the army (he earned a Purple Heart). Over two decades later, in 1969, Vonnegut published the bestselling novel Slaughterhouse-Five, which gave readers a fictionalized account of his wartime imprisonment. He later said that only one person benefited from the raid in Dresden: him. "I got three dollars for each person killed. Imagine that," he said.

4. CONTRARY TO RUMORS, HE WASN’T FRAT BUDDIES WITH DR. SEUSS.

An urban legend suggests that Vonnegut and Theodor Geisel (a.k.a. Dr. Seuss) were college friends who spent time together in the same fraternity. But according to Snopes, the tale of Geisel and Vonnegut’s friendship is greatly exaggerated … that is, it’s false. The two authors probably never met, and they didn’t attend any of the same schools (plus, Geisel was 18 years older than Vonnegut). Geisel did, however, once visit a friend who belonged to Cornell’s Delta Upsilon fraternity. Geisel drew a mural on the wall of the fraternity’s basement, and Vonnegut saw his drawings at Cornell a decade later as a student.

5. HE HELD A SERIES OF ODD JOBS TO SUPPORT HIS FAMILY.

In 1947, Vonnegut began working in public relations for General Electric, an experience that he drew upon to write Cat’s Cradle. He wrote articles and short stories for magazines such as Collier’s and The Saturday Evening Post, and his first novel, Player Piano, was published in 1952. Vonnegut then briefly wrote for Sports Illustrated, managed a Saab car dealership in Massachusetts (the first in the U.S.), and worked as an English teacher.

6. HE ADOPTED HIS SISTER’S THREE KIDS.

In the late 1950s, Vonnegut’s sister, Alice, died of cancer and Alice’s husband died in a train accident within the span of a few days. Although Vonnegut already had three children with his wife, he adopted his sister’s three sons. Since he now had six children to support, Vonnegut spent even more time writing to earn money.

7. HE ATTEMPTED SUICIDE.

Although Slaughterhouse-Five made him a famous, bestselling author, Vonnegut struggled with depression in the midst of his literary success. After getting divorced in 1971, he lived alone in New York City and had trouble writing. His son became psychotic, and although he married his second wife in 1979 (and they adopted a daughter together), his depression got worse. In 1984, he tried to kill himself by overdosing on sleeping pills and alcohol, an experience he wrote about in 1991 in Fates Worse Than Death, a collection of essays.

8. HE GRADED ALL HIS BOOKS.

In an interview with Charlie Rose, Vonnegut discussed his grading system for his books (he also wrote about this system in Palm Sunday, a collection of his works published in 1981). He gave himself an A+ for his writing in Cat’s Cradle and Slaughterhouse-Five but wasn’t as generous with Happy Birthday, Wanda June or Slapstick, which both received Ds.

9. HE LOVED WATCHING CHEERS.

In 1991, while speaking to the press to promote his Showtime television show Vonnegut’s Monkey House, he extolled the virtues of the NBC show Cheers. "I’d rather have written Cheers than anything I’ve written," he said. Although he viewed television in general with skepticism, he made an exception for the long-running sitcom, calling it television’s one comic masterpiece: "Every time anybody opens his or her mouth on that show, it’s significant. It’s funny," he said.

10. HE TRIED TO STOP SMOKING BUT GAINED TOO MUCH WEIGHT.

A lifelong smoker, Vonnegut began smoking cigarettes as a young teenager. Interviews with the author described his chain-smoking, his preferred brand (Pall Mall), and his frequent coughing and wheezing. Vonnegut admitted that he quit smoking twice, but neither attempt succeeded long-term. "Once I did it cold turkey, and turned into Santa Claus. I became roly-poly. I was approaching 250 pounds," he told the Paris Review. The second time, his lack of smoking made him "unbearably opinionated" and curtailed his writing time. "I didn’t even write letters anymore. I had made a bad trade, evidently. So I started smoking again," he said.

11. THANKS TO CAT’S CRADLE, HE FINALLY GOT HIS MASTER'S DEGREE.

While studying anthropology as a young man at the University of Chicago, Vonnegut wrote his graduate thesis comparing 19th century Cubist painters to Native American artists. Vonnegut later explained that the faculty rejected his dissertation, and he dropped out of his master’s program there: "I left Chicago without writing a dissertation—and without a degree. All my ideas for dissertations had been rejected, and I was broke, so I took a job as a P.R. man for General Electric in Schenectady." But the quality of his novel Cat’s Cradle, published in 1963, persuaded University of Chicago faculty to accept the novel as his dissertation. So 20 years after he dropped out, Vonnegut finally earned his master’s degree in anthropology.

12. HE HAS OVER 210,000 TWITTER FOLLOWERS.

Although Vonnegut died in 2007 at 84 years old, his ideas live on in 140 characters or less. A Twitter account dedicated to the writer tweets his quotes several times a day to more than 215,000 followers. Examples of his tweets? "How embarrassing to be human," and "We could have saved the Earth but we were too damned cheap." Fittingly, the account follows just one person, @TheMarkTwain, for Vonnegut greatly admired the Tom Sawyer and Huckleberry Finn author.

13. THE VONNEGUT MEMORIAL LIBRARY CONTINUES HIS LEGACY.

Located in his birthplace of Indianapolis, The Kurt Vonnegut Memorial Library honors the writer’s achievements and keeps his legacy alive. Opened in 2010, the library displays signed copies of Vonnegut’s books as well as early rejection letters. Visitors can also see his drawings, examine family photos, and view his typewriter, cigarettes, and Purple Heart. The library works to fight censorship, a cause that Vonnegut strongly believed in, by giving free copies of Slaughterhouse-Five to students whose schools have banned the book. So it goes.

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