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10 Works of Literature That Were Really Hard to Write

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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15 Things You Might Not Know About Your Favorite Poets
English Romantic poet Lord Byron being visited by his muse.
English Romantic poet Lord Byron being visited by his muse.
Hulton Archive, Getty Images

When we think of poets, too often we imagine posh parlors, stoic sophistication, and austere attitudes. But the lives, hobbies, and eccentricities of some of the world's greatest poets made them much more than titans of the turn of phrase. Here are 15 fun facts about some of your favorite poets.

1. CHARLES BUKOWSKI WAS A CAT PERSON.

portrait of Charles Bukowski
GABRIEL BOUYS, AFP / Getty Images

This transgressive German-American poet was once declared a "laureate of American lowlife" by Time magazine. But Bukowski had a soft spot for felines, and owned a pet cat called Minx. In the poem "My Cats," he wrote, "when I am feeling/low/all I have to do is/watch my cats/and my/courage/returns."

2. ELIZABETH BARRETT BROWNING'S LAST WORDS WERE FITTINGLY SWEET.

Portrait of Elizabeth Barrett Browning
Hulton Archive, Getty Images

Many of the Victorian-era writer's romantic poems, like "How Do I Love Thee?", were inspired by her beloved husband, poet Robert Browning. And even her death had an air of romance—at 55, she was dying of an undetermined illness (she had spent most of her life in poor health). Browning held her in his arms and asked how she was feeling. Her final word was simply, "Beautiful."

3. PABLO NERUDA PREFERRED TO HANDWRITE HIS POEMS IN GREEN INK.

portrait of Pablo Neruda
STF/AFP/Getty Images

The Pulitzer Prize-winner from Chile favored a fountain pen that he filled with his signature color. It's popularly believed that Neruda, who blended surrealism and politics into his poetry, saw green as the color of hope.

4. IN AN EYEBROW-RAISING DEDICATION PAGE, E.E. CUMMINGS ONCE CALLED OUT THOSE WHO SPURNED HIM.

E.E. Cummings
Hulton Archive, Getty Images

Even after releasing a novel, poetry collections, and plays, American writer E.E. Cummings's proposed collection 70 Poems was rejected by 14 publishers. With a loan from his mother, he finally managed to publish the book in 1935, but with two noteworthy revisions. First, he changed its title to No Thanks, a reference to the dismissal letters he'd received. And on its dedication page, Cummings printed a concrete poem—a poem written in the shape of a funereal urn, listing the names of every publisher who had rejected him.

5. SAPPHO MIGHT HAVE BEEN THE ADELE OF HER DAY.

Sappho
Picture Post, Getty Images

This archaic Greek poet is touted as one of the greatest to ever work in the medium. However, ancient texts described her writing as melê, which translates to "songs." Historians still debate how Sappho's works were performed, but this description suggests they were lyrics set to music, meaning Sappho may have been a popular songwriter, more than a poet. It's speculated Sappho's fans copied her lyrics onto papyrus and pottery, unintentionally preserving her talent and verses for thousands of years.

6. SHEL SILVERSTEIN WAS AN AWARD-WINNING SONGWRITER.

A Shel Silverstein poem
Jabiz Raisdana, Flickr // CC BY-NC 2.0

Shel Silverstein is best known for his illustrated poetry books for children like Where The Sidewalk Ends and A Light In the Attic, but the American humorist also earned Golden Globe and Academy Award nominations in 1991 for writing the song "I'm Checkin' Out," which was performed by Meryl Streep at the end of the movie Postcards From the Edge. Two decades earlier, he won the Grammy for Best Country Song for penning the playful (if violent) "A Boy Named Sue," which Johnny Cash also won a performance Grammy for.

7. LANGSTON HUGHES MAY HAVE BEEN A KEY INFLUENCE ON MARTIN LUTHER KING, JR.

Langston Hughes.
Hulton Archive, Getty Images

The popular poet of the Harlem Renaissance and the bold Civil Rights leader were friends who exchanged letters, including one where King told Hughes, "I can no longer count the number of times and places … in which I have read your poems."

Scholars have long explored how this friendship shaped both men. But English professor Jason Miller illuminates striking similarities, which suggest Hughes's poem "I Dream A World" may have inspired King's iconic "I Have a Dream" speech. Hughes wrote, "A world I dream where black or white,/Whatever race you be,/Will share the bounties of the earth/And every man is free." In comparison, King's 1953 speech included, "I have a dream that one day … little black boys and black girls will be able to join hands with little white boys and white girls and walk together as sisters and brothers."

8. FAMED CHICAGOAN GWENDOLYN BROOKS WAS AN INSPIRATION TO ANOTHER YOUNG CHICAGO CREATIVE.

sketch of Gwendolyn Brooks
Burns Library, Boston College, Flickr // CC BY-NC-ND 2.0

In an interview early in his career, Kanye West noted that Brooks—the first African-American to win a Pulitzer Prize, for her portrayal of a young black girl growing up on Chicago's South Side—was one of his favorite writers. West recounted how when he was in grade school, he'd met Brooks at a dinner for local students—she was an educator and longtime advocate for children's education. "They had a dinner and Gwendolyn Brooks was there and everyone was reading their poems," he said. "She said, 'Do you have a poem?' I said [switches to a high-pitched voice], 'No, but I can write one real quick.' I went in the back, wrote a poem, and then read it for her and the 40 staff members."

9. ONE POEM HELPED EDNA ST. VINCENT MILLAY GAIN BOTH NATIONAL ATTENTION AND A PATRON TO FUND HER EDUCATION.

portrait of Edna St. Vincent Millay
Hulton Archive, Getty Images

Growing up on the coast of Maine, Edna was an outgoing tomboy who preferred to be called "Vincent." Her parents had divorced when she was young, and her mother was raising three young girls on her own. They were quite poor, but her mother had long encouraged her writing pursuits, and when Edna was 20, Cora Millay insisted she enter a poem in a contest."Renascence" didn't win, but there was such an outcry from readers and columnists that it gave Edna instant clout. At a reading she gave not long after, one guest was so impressed that she offered to help fund Millay's college education and at age 21, Millay enrolled at Vassar College.

10. ELIZABETH BISHOP REFUSED TO BE INCLUDED IN GENDER-SPECIFIC ANTHOLOGIES.

Elizabeth Bishop
Elizabeth Bishop in 1934, in the Vassar College yearbook.
Wikimedia Commons // Public Domain

Pulitzer Prize- and National Book Award-winning Elizabeth Bishop loathed when her gender was mentioned in connection with her talent as a writer. When she was asked in the early '70s if she would allow one of her poems to be included in an anthology called The Women Poets in English, Bishop responded that "(Men and women) do not write differently," adding, "Why not Men Poets in English? Don't you see how silly it is? … I don't like things compartmentalized like that." She echoed this belief throughout her career. "Literature is literature, no matter who produces it."

11. DENIED A DOG, LORD BYRON MADE A BEAR HIS PET.

portrait of Lord Byron
Hulton Archive, Getty Images

When the English nobleman was a young, cheeky student at Trinity College in Cambridge, the school had a rule against students keeping dogs. Byron—who so famously loved his Newfoundland, Boatswain, that he had a tomb inscribed with a poem for the dog after its death in 1808—obliged, but instead took advantage of the language and purchased a bear instead, which he would walk around the grounds on a chain leash.

In an 1807 letter to a friend, Byron wrote of his unusual pet, "I have got a new friend, the finest in the world, a tame bear. When I brought him here, they asked me what to do with him, and my reply was, 'he should sit for a fellowship'."

12. AFTER HER DEATH, DOROTHY PARKER'S ASHES SPENT NEARLY 20 YEARS IN A FILING CABINET.

Dorothy Parker
Evening Standard, Getty Images

When poet and satirist Dorothy Parker died in 1967, she left instructions for her entire estate to be left to Martin Luther King, Jr. and for her body to be cremated—she didn't, however, specify where she wanted her ashes interned or scattered. After the executor of her estate failed to claim her ashes from the mortuary, her attorney collected them, put them in a filing cabinet, and left them there until 1987, when a Parker biographer mentioned wanting to visit her grave. Her remains were eventually moved to a memorial garden built by the NAACP (who now controls her estate, following King's death). The plaque above her urn aptly reads, "Excuse My Dust."

13. AFTER HIS UNEXPECTED DEATH, PERCY BYSSHE SHELLEY'S WIFE KEPT A GRISLY MEMENTO.

Portrait of Percy Bysshe Shelley
Hulton Archive, Getty Images

This English Romantic was husband to Mary Shelley, author of Frankenstein. So perhaps it's fitting that when he drowned tragically at 29, Mary held onto his heart, literally. The story goes that the organ did not burn when the rest of his remains were cremated. So his loving widow wrapped it in a silken shroud, and took it with her wherever she went. Nearly 70 years later, Shelley's heart was finally buried in the family vault with the couple's son.

14. EZRA POUND CONCOCTED A PECULIAR PLAN TO CONVINCE T.S. ELIOT TO QUIT HIS DAY JOB.

Ezra Pound in Italy
Ezra Pound
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Ezra Pound was so in awe of fellow American ex-pat T.S. Eliot's 1922 masterpiece "The Waste Land," that he felt the London bank teller should devote himself completely to poetry. Pound even crowdfunded to make it happen, but without consulting Eliot first to see if he'd be game. This impulsive plan sparked a scandal when Eliot wouldn't leave the bank (he stayed in the job for another couple of years, before moving to a publishing house). But Pound was right about his instinct to help foster Eliot's career—20-some years later, Eliot won the Nobel Prize in Literature.

15. WILLIAM CARLOS WILLIAMS BELIEVED HIS WORK AS A DOCTOR MADE HIM A BETTER POET.

photo of William Carlos Williams
Beinecke Rare Book & Manuscript Library, Yale University, Wikimedia Commons // Public Domain

While many artists bemoan their survival jobs, Williams relished his. Trained in pediatrics and general medicine, Williams found inspiration in his patients. And in his 1967 autobiography, he aimed to explain how he felt his two jobs served to benefit each other: "They are two parts of a whole. It is not two jobs at all … one rests the man when the other fatigues him."

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12 Things You Might Not Know About Beverly Cleary
Public Domain, Wikimedia Commons
Public Domain, Wikimedia Commons

Moving, relatable, and frequently hilarious, Beverly Cleary’s stories have been captivating readers of all ages for more than 60 years. From Ramona Quimby to Socks the Cat, Cleary's characters—and the tales they inhabit—are still going strong all these decades later. Here’s what you might not know about one of the world’s favorite children’s authors, who turns 102 years old today.

1. SHE'S A FORMER LIBRARIAN.

After graduating in 1939 from the University of Washington with a Library Science degree, Cleary worked as a children’s librarian in Yakima. 

2. SHE HELPED IMPROVE THE LEAVE IT TO BEAVER FRANCHISE.

Cleary once wrote a pair of original Leave It to Beaver tie-in stories starring Wally and The Beav which, according to several letters she received, many fans found much more enjoyable than the series’ film adaptation. (Her explanation? “I cut out dear old Dad’s philosophizing.”)

3. YOU CAN VISIT THE BEVERLY CLEARY SCULPTURE GARDEN IN PORTLAND, OREGON.

Many of Cleary’s best-known stories were partially set in Portland’s Grant Park (she grew up nearby) and, as a loving nod, the city unveiled statues of Ramona Quimby, Henry Huggins, and Ribsy the dog at the park in 1995.

4. SHE'S ALWAYS SYMPATHIZED WITH STRUGGLING READERS.

Getting put into the lowest reading circle in first grade almost made young Cleary resent books. Phonic lists were a drag and being force-fed Dick & Jane-style narratives was flat-out excruciating. “[We] wanted action. We wanted a story,” she lamented in her autobiography. It was an experience Cleary never forgot. Since then, she claimed to have always kept children who might be undergoing similar trials in mind while writing.

5. SHE'D WRITE AND BAKE SIMULTANEOUSLY.

Many authors crank up their favorite tunes during scribing sessions, but Cleary had a different approach. “I used to bake bread while I wrote," she once explained. "I’d mix the dough up and sit down and start to write. After a while, the dough would rise and I’d punch it down and write some more. When the dough rose the second time, I’d put it in the oven and have the yeasty smell of bread as I typed.”

6. THERE'S AN ELEMENTARY SCHOOL NAMED IN HER HONOR.

Beverly Cleary Elementary is an Oregon K-8 school with three campuses in Portland, Oregon.

7. DESPITE HER PARENTS' OBJECTIONS, CLEARY ELOPED WITH THE MAN SHE LOVED.

“Gerhart” is the pseudonym her memoirs give to the fellow Beverly’s folks actually tried setting her up with, though the pair shared virtually no chemistryClarence Cleary, her future husband, was a kind-hearted economics and history student she met in college. He was also Roman Catholic, which didn’t sit well with her Presbyterian parents. Undaunted, Beverly Atlee Bunn eloped and became Beverly Cleary in 1940. The couple would remain together until Clarence’s death in 2004.

8. HARPER COLLINS PUBLISHING CREATED A HOLIDAY FOR HER BIRTHDAY.

Kids reading outdoors
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It's called D.E.A.R. (Drop Everything And Read), and though they encourage you to celebrate all the time, April 12 is the official date in honor of Cleary's birthday.

9. THE LIBRARY OF CONGRESS DECLARED HER A "LIVING LEGEND."

This award is exclusively granted to “artists, writers, activists, filmmakers, physicians, entertainers, sports figures, and public servants who have made significant contributions to America’s diverse cultural, scientific, and social heritage.” Cleary received her title in 2000, joining the ranks of Judy Blume, Muhammad Ali, and Madeleine Albright.

10. SHE HAS A VERY WISE WRITING MANTRA.

When she was still a little girl, Cleary’s mother, an ex-teacher, gave her this advice: “The best writing is simple writing. And try to write something funny. People enjoy reading anything that makes them laugh.” Another tip that stuck with her came from a college professor, who often said, “The proper subject of the novel is the universal human experience.”

11. SHE'S A CAT LOVER.

Cleary has owned several cats over the years, one of whom used to resent having to compete with her typewriter for attention and would sit on the keys in protest.

12. SHE HAS A THEORY ABOUT WHY KIDS LOVE RAMONA QUIMBY SO MUCH.

“Because [Ramona] does not learn to be a better girl. I was so annoyed with the books in my childhood, because children always learned to be ‘better’ children and, in my experience, they didn’t. They just grew, and so I started Ramona … and she has never reformed. [She’s] really not a naughty child, in spite of the title Ramona the Pest. Her intentions are good, but she has a lot of imagination, and things sometimes don’t turn out the way she expected.”

A version of this story originally ran in 2014.

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