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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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Ernest Hemingway’s Guide to Life, In 20 Quotes
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Central Press/Getty Images

Though he made his living as a writer, Ernest Hemingway was just as famous for his lust for adventure. Whether he was running with the bulls in Pamplona, fishing for marlin in Bimini, throwing back rum cocktails in Havana, or hanging out with his six-toed cats in Key West, the Nobel and Pulitzer Prize-winning author never did anything halfway. And he used his adventures as fodder for the unparalleled collection of novels, short stories, and nonfiction books he left behind, The Sun Also Rises, A Farewell to Arms, Death in the Afternoon, For Whom the Bell Tolls, and The Old Man and the Sea among them.

On what would be his 118th birthday—he was born in Oak Park, Illinois on July 21, 1899—here are 20 memorable quotes that offer a keen perspective into Hemingway’s way of life.

ON THE IMPORTANCE OF LISTENING

"I like to listen. I have learned a great deal from listening carefully. Most people never listen."

ON TRUST

"The best way to find out if you can trust somebody is to trust them."

ON DECIDING WHAT TO WRITE ABOUT

"I never had to choose a subject—my subject rather chose me."

ON TRAVEL

"Never go on trips with anyone you do not love."

Ernest Hemingway Photograph Collection, John F. Kennedy Presidential Library and Museum, Boston. [1], Public Domain, Wikimedia Commons

ON THE RELATIONSHIP BETWEEN INTELLIGENCE AND HAPPINESS

"Happiness in intelligent people is the rarest thing I know."

ON TRUTH

"There's no one thing that is true. They're all true."

ON THE DOWNSIDE OF PEOPLE

"The only thing that could spoil a day was people. People were always the limiters of happiness, except for the very few that were as good as spring itself."

ON SUFFERING FOR YOUR ART

"There is nothing to writing. All you do is sit down at a typewriter and bleed."

ON TAKING ACTION

"Never mistake motion for action."

ON GETTING WORDS OUT

"I wake up in the morning and my mind starts making sentences, and I have to get rid of them fast—talk them or write them down."

Photograph by Mary Hemingway, in the Ernest Hemingway Photograph Collection, John F. Kennedy Presidential Library and Museum, Boston., Public Domain, Wikimedia Commons

ON THE BENEFITS OF SLEEP

"I love sleep. My life has the tendency to fall apart when I'm awake, you know?"

ON FINDING STRENGTH 

"The world breaks everyone, and afterward, some are strong at the broken places."

ON THE TRUE NATURE OF WICKEDNESS

"All things truly wicked start from innocence."

ON WRITING WHAT YOU KNOW

"If a writer knows enough about what he is writing about, he may omit things that he knows. The dignity of movement of an iceberg is due to only one ninth of it being above water."

ON THE DEFINITION OF COURAGE

"Courage is grace under pressure."

ON THE PAINFULNESS OF BEING FUNNY

"A man's got to take a lot of punishment to write a really funny book."

By Ernest Hemingway Photograph Collection, John F. Kennedy Presidential Library and Museum, Boston. - JFK Library, Public Domain, Wikimedia Commons

ON KEEPING PROMISES

"Always do sober what you said you'd do drunk. That will teach you to keep your mouth shut."

ON GOOD VS. EVIL

"About morals, I know only that what is moral is what you feel good after and what is immoral is what you feel bad after."

ON REACHING FOR THE UNATTAINABLE

"For a true writer, each book should be a new beginning where he tries again for something that is beyond attainment. He should always try for something that has never been done or that others have tried and failed. Then sometimes, with great luck, he will succeed."

ON HAPPY ENDINGS

"There is no lonelier man in death, except the suicide, than that man who has lived many years with a good wife and then outlived her. If two people love each other there can be no happy end to it."

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Scientists Study the Starling Invasion Unleashed on America by a Shakespeare Fan

On a warm spring day, the lawn outside the American Museum of Natural History in Manhattan gleams with European starlings. Their iridescent feathers reflect shades of green and indigo—colors that fade to dowdy brown in both sexes after the breeding season. Over the past year, high school students from different parts of the city came to this patch of grass for inspiration. "There are two trees at the corner I always tell them to look at," Julia Zichello, senior manager at the Sackler Educational Lab at the AMNH, recalls to Mental Floss. "There are holes in the trees where the starlings live, so I was always telling them to keep an eye out."

Zichello is one of several scientists leading the museum's Science Research Mentoring Program, or SRMP. After completing a year of after-school science classes at the AMNH, New York City high school students can apply to join ongoing research projects being conducted at the institution. In a recent session, Zichello collaborated with four upperclassmen from local schools to continue her work on the genetic diversity of starlings.

Before researching birds, Zichello earned her Ph.D. in primate genetics and evolution. The two subjects are more alike than they seem: Like humans, starlings in North America can be traced back to a small parent population that exploded in a relatively short amount of time. From a starting population of just 100 birds in New York City, starlings have grown into a 200-million strong flock found across North America.

Dr. Julia Zichello
Dr. Julia Zichello
©AMNH

The story of New York City's starlings began in March 1890. Central Park was just a few decades old, and the city was looking for ways to beautify it. Pharmaceutical manufacturer Eugene Schieffelin came up with the idea of filling the park with every bird mentioned in the works of William Shakespeare. This was long before naturalists coined the phrase "invasive species" to describe the plants and animals introduced to foreign ecosystems (usually by humans) where their presence often had disastrous consequences. Non-native species were viewed as a natural resource that could boost the aesthetic and cultural value of whatever new place they called home. There was even an entire organization called the American Acclimatization Society that was dedicated to shipping European flora and fauna to the New World. Schieffelin was an active member.

He chose the starling as the first bird to release in the city. It's easy to miss its literary appearance: The Bard referenced it exactly once in all his writings. In the first act of Henry IV: Part One, the King forbids his knight Hotspur from mentioning the name of Hotspur's imprisoned brother Mortimer to him. The knight schemes his way around this, saying, "I'll have a starling shall be taught to speak nothing but 'Mortimer,' and give it him to keep his anger still in motion."

Nearly three centuries after those words were first published, Schieffelin lugged 60 imported starlings to Central Park and freed them from their cages. The following year, he let loose a second of batch of 40 birds to support the fledgling population.

It wasn't immediately clear if the species would adapt to its new environment. Not every bird transplanted from Europe did: The skylark, the song thrush, and the bullfinch had all been subjects of American integration efforts that failed to take off. The Acclimatization Society had even attempted to foster a starling population in the States 15 years prior to Schieffelin's project with no luck.

Then, shortly after the second flock was released, the first sign of hope appeared. A nesting pair was spotted, not in the park the birds were meant to occupy, but across the street in the eaves of the American Museum of Natural History.

Schieffelin never got around to introducing more of Shakespeare's birds to Central Park, but the sole species in his experiment thrived. His legacy has since spread beyond Manhattan and into every corner of the continent.

The 200 million descendants of those first 100 starlings are what Zichello and her students made the focus of their research. Over the 2016-2017 school year, the group met for two hours twice a week at the same museum where that first nest was discovered. A quick stroll around the building reveals that many of Schieffelin's birds didn't travel far. But those that ventured off the island eventually spawned populations as far north as Alaska and as far south as Mexico. By sampling genetic data from starlings collected around the United States, the researchers hoped to identify how birds from various regions differed from their parent population in New York, if they differed at all.

Four student researchers at the American Museum of Natural History
Valerie Tam, KaiXin Chen, Angela Lobel and Jade Thompson (pictured left to right)
(©AMNH/R. Mickens)

There are two main reasons that North American starlings are appealing study subjects. The first has to do with the founder effect. This occurs when a small group of individual specimens breaks off from the greater population, resulting in a loss of genetic diversity. Because the group of imported American starlings ballooned to such great numbers in a short amount of time, it would make sense for the genetic variation to remain low. That's what Zichello's team set out to investigate. "In my mind, it feels like a little accidental evolutionary experiment," she says.

The second reason is their impact as an invasive species. Like many animals thrown into environments where they don't belong, starlings have become a nuisance. They compete with native birds for resources, tear through farmers' crops, and spread disease through droppings. What's most concerning is the threat they pose to aircraft. In 1960, a plane flying from Boston sucked a thick flock of starlings called a murmuration into three of its four engines. The resulting crash killed 62 people and remains the deadliest bird-related plane accident to date.

Today airports cull starlings on the premises to avoid similar tragedies. Most of the birds are disposed of, but some specimens are sent to institutions like AMNH. Whenever a delivery of dead birds arrived, it was the students' responsibility to prep them for DNA analysis. "Some of them were injured, and some of their skulls were damaged," Valerie Tam, a senior at NEST+m High School in Manhattan, tells Mental Floss. "Some were shot, so we had to sew their insides back in."

Before enrolling in SRMP, most of the students' experiences with science were limited to their high school classrooms. At the museum they had the chance to see the subject's dirty side. "It's really different from what I learned from textbooks. Usually books only show you the theory and the conclusion, but this project made me experience going through the process," says Kai Chen, also a senior at NEST+m.

After analyzing data from specimens in the lab, an online database, and the research of previous SRMP students, the group's hypothesis was proven correct: Starlings in North America do lack the genetic diversity of their European cousins. With so little time to adapt to their new surroundings, the variation between two starlings living on opposite coasts could be less than that between the two birds that shared a nest at the Natural History Museum 130 years ago.

Students label samples in the lab.
Valerie Tam, Jade Thompson, KaiXin Chen and Angela Lobel (pictured left to right) label samples with Dr. Julia Zichello.
©AMNH/C. Chesek

Seeing how one species responds to bottlenecking and rapid expansion can provide important insight into species facing similar conditions. "There are other populations that are the same way, so I think this data can help [scientists],” Art and Design High School senior Jade Thompson says. But the students didn't need to think too broadly to understand why the animal was worth studying. "They do affect cities when they're searching for shelter," Academy of American Studies junior Angela Lobel says. “They can dig into buildings and damage them, so they're relevant to our actual homes as well.”

The four students presented their findings at the museum's student research colloquium—an annual event where participants across SRMP are invited to share their work from the year. Following their graduation from the program, the four young women will either be returning to high school or attending college for the first time.

Zichello, meanwhile, will continue where she left off with a new batch of students in the fall. Next season she hopes to expand her scope by analyzing older specimens in the museum's collections and obtaining bird DNA samples from England, the country the New York City starlings came from. Though the direction of the research may shift, she wants the subject to remain the same. "I really want [students] to experience the whole organism—something that's living around them, not just DNA from a species in a far-away place." she says. "I want to give them the picture that evolution is happening all around us, even in urban environments that they may not expect."

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