Macho Facts About Ernest Hemingway, The Lost Writer

Rachel Seigel

Ernest Hemingway and his notorious reputation loom large over the 20th century…but to be honest, most people don’t even know the half of it. This hard-drinking, fast-living, bad-loving writer had a life most people only get nightmares about, and it all led up to his infamously tragic end. Get out your tumblers and highball glasses, because you’re going to need them for this one.


Ernest Hemingway Facts

1. His Family Was Eerily Normal

Ernest Hemingway wasn’t like other boys, but it didn’t seem that way at first. He was born into a comfortable middle-class family in idyllic Oak Park, Illinois, which architect Frank Lloyd Wright once described as having, “So many churches for so many good people to go to.” But under the cover of this pleasant setting, the Hemingway family was downright disturbing.

2. His Mother Controlled Him

The family matriarch, Grace, was extremely domineering and paid special “attention” to her eldest son Ernest. Ernest recalled how his mother forced him to learn the cello even he staunchly refused to practice, as well as how she had his father Clarence wrapped around her finger. Only, when it comes to Hemingway’s relationship with his mother, that just the beginning of the bizarre nightmare.

3. He Masqueraded As A Girl

Ernest and his older sister Marcelline were very close in age, and this drove his mother to make a very creepy decision. For some reason, Grace believed the “healthiest” thing to do was to raise the siblings as twin girls. She dressed them both up in frilly Victorian-style clothing, and until Ernest was three she refused to cut his hair, preferring to let him and Marcelline get mistaken for each other. Did this negatively affect Ernest? Oh heck yes it did.

4. He Genuinely Hated His Mother

Given this upbringing, it’s no wonder that Ernest absolutely despised his mother, and he wasn’t ashamed to shout it from the rooftops when he grew up. One of Hemingway’s friends, Major General Charles Lanham, admitted that Hemingway “was the only man he ever knew who really hated his mother.” Soon enough, this would devolve into a much darker disdain…but before that happened, more trauma was on the way.

5. He Tried To Prove Himself

When Hemingway grew into a gangly 18-year-old, he was (unsurprisingly) desperate to prove his masculinity. Besides being an avid boxer and hunter, he also wanted to add “soldier” to his list. He tried out for the US Army to serve in WWI and received a rejection for his poor eyesight, but this didn’t slow him down one bit. Hemingway simply went a different route and signed up with the Red Cross as an ambulance driver in Italy. His mission finally accomplished, Ernest went into Europe with high ideals—and came out a haunted man.

6. He Had A Brutal Coming Of Age

Just months after landing in Europe, Hemingway went through a violent awakening. On July 8, he was bringing canteen supplies to men on the front line when mortar fire caught him and he went down hard. Shrapnel went into both of his legs, but even in the chaos of the conflict, he helped more severely wounded men to safety. It was a baptism by fire, and there was more to come.

7. He Fell In Love With His Nurse

After successful emergency surgery on his legs, Hemingway had to spend the next six months recovering in a hospital in Milan. At first, despite his harrowing path there, his stay was a happy one, and he even fell in love with his nurse, Agnes von Kurowsky. Although Agnes was a full seven years old than the teenager, Hemingway thought she reciprocated his feelings. Sadly, they were more doomed than Romeo and Juliet.

8. He Had A Long Distance Romance

In January of 1919, Hemingway was well enough to leave the hospital in Milan and go back home to the United States. Full of hope and joy for his future with his love, Hemingway made plans for Agnes to join him in just a few short months, where they would then marry stateside and begin their happily ever after. Well, this is right about when Agnes shattered his heart into a million pieces.

9. His Lover Betrayed Him

After waiting through the winter for news of Agnes, Hemingway finally got a letter from her in March 1919. Its contents nearly killed him. In the message, Agnes confessed to Hemingway that she had met an Italian officer in his absence, and she was now the man’s fiancee. Hemingway’s first love was dust, and his reaction was nothing short of tragic.

10. He Never Wanted To Trust A Woman

If Hemingway’s issues with women began with his mother, they spread like wildfire when Agnes betrayed him. Her letter hurt more than the shrapnel, and he could never have trust in romance again. Indeed, as we’ll see, he would spend the rest of his life getting vengeance on Agnes’s memory through a series of failed relationships, each one more bitter than the last. Oh, and it didn’t take long for him to find his first “replacement.”

11. He Went On The Rebound

After WWI, Hemingway eventually ended up in Chicago, starting work as a journalist, writing short stories on the side, and living with his friends. He was trying to get his life back on track, but when the St. Louis native Hadley Richardson rolled into town, all bets were off. A shy, nurturing redhead, Richardson immediately charmed Hemingway. But there was a dark side to their flirtation.

12. He Replaced His Ex

Oh sure, the young lovers had things to bond about—after all, Richardson grew up with an overbearing mother just like Hemingway—but that wasn’t why Hemingway liked her so much. Uncomfortably enough, Richardson was eight years older than Hemingway, almost the exact same age gap as his ex Agnes, and people have called Hadley “evocative” of his long-lost love.

With his mommy issues and Agnes issues firmly in play, Hemingway just kept the bad decisions rolling.

13. He Rushed Into Marriage

This time, Hemingway wanted to re-write history, and he refused to let Richardson become the (second) one who got away. Almost from the moment that he met her, Hemingway claimed Richardson was the woman he was going to marry. On September 3, 1921, he made good on his promise, and the couple tied the knot in a ceremony with little fanfare. Then Hemingway met his destiny.

14. He Became An Ex-Pat

Just months after marrying Richardson, Hemingway got the opportunity to be the foreign correspondent for the Toronto Star. Accordingly, the newlyweds headed over to the continent to live in Paris alongside some of the day’s biggest writers, including James Joyce and Gertrude Stein. This is the most famous part of Hemingway’s life for a reason: The budding writer had it all, including a wife who loved him, a European adventure, and his whole future ahead of him. Oh boy, it went badly.

15. He Made Famous Friends

Once more, this new phase of Hemingway’s life started out well. Hemingway and his new wife posted up in the Latin Quarter, and soon he was rubbing shoulders with Stein, who then helped Hemingway get his literary career further off the ground along with the rest of the “Lost Generation” of men who were recovering from WWI. Besides that, Hemingway also had his first child, a boy named Jack, around this time. But there was also too much of a good thing…

16. He Had A Notorious Drinking Buddy

Within months, Hemingway had become fast friends with the modernist crowd in Paris—and bosom buddies with all the bartenders in the city, too. In no time, he began to develop disturbing habits. He and James Joyce would often go on “alcoholic sprees” together, and it was here that Hemingway began to develop his macho persona, leaning in on his, “tall, handsome, muscular, [and] broad-shouldered” looks. And, uh…he would need them.

17. He Loved Getting Into Bar Brawls

Joyce and Hemingway may have bonded, but they couldn’t have been more different in appearance or personality. Joyce was physically weak and unattractive, while Hemingway had boxed from a young age. According to stories, whenever he was with Hemingway, Joyce would pick drunken bar fights and then hide behind Hemingway, shouting, “Deal with him Hemingway! Deal with him!” Hemingway, for his part, was more than happy to accommodate. And those weren’t the only fights he was getting into.

18. He Started A Legendary Feud

All this carousing might have made some good vignettes for Midnight in Paris, but Hemingway was getting quite a big head living it up with his boys. Eventually, his relationship with Gertrude Stein, who had given him his start and was godmother to his son Jack, began to deteriorate. Things got so bad that the two of them became both personal and literary rivals.…and then Hemingway experienced every writer’s worst nightmare.

19. He Suffered A Huge Loss

While in Paris, Hemingway wrote up a storm, generally collecting his most recent writings in a single suitcase. Can you see where this is going? One day in 1922, Hadley Richardson was traveling to meet her husband via the Gare de Lyon, and in the chaos of getting on the train, she forgot his precious suitcase at the station. Tragically, they never found it again, and pages upon pages of future manuscripts disappeared into thin air.

Hemingway tried to recover from his enormous loss, and published his first book, 1923’s Three Stories and Ten Poems, with some of the only remaining writing he had. But he also coped in more destructive ways.

20. He Saw F. Scott Fitzgerald’s “Package”

Besides downing pints with James Joyce, Hemingway also fell in with notorious party couple Zelda and F. Scott Fitzgerald. And let me tell you, their antics were not safe for work. On one infamous occasion at a restaurant, Zelda was mocking her husband F. Scott’s, er, manhood and insisting he could never truly please a lover in the bedroom. Our boy’s response was pure vintage Hemingway.

Hemingway offered to take a look himself in the men’s room and give his own appraisal. When he did, he was happy to report Fitzgerald’s twigs and berries were perfectly satisfactory. That said, Fitzgerald and Hemingway’s relationship was full of more than just sexual tension…

21. He Made A Frenemy

In truth, Hemingway’s new friendship was shot through with toxicity. Practically right at the moment that the two met, Fitzgerald had just finished his 1925 masterpiece The Great Gatsby, and when Hemingway read it, he was beside himself with jealously. Theirs was a dynamic of “admiration and hostility,” and Hemingway soon swore that his next piece of writing would be a novel, just so he could do better than Gatsby.

The work it would take for him to get there was nothing short of ruinous—to his friends, to himself, and to his marriage.

22. He Had A Dangerous Obsession

In the mid-1920s, Hemingway became obsessed with bullfighting, visiting the violent and dangerous bullfights in Pamplona, Spain several times over. Accordingly, Hemingway decided his first novel, The Sun Also Rises, would be about the corrida, and he packed up Hadley Richardson and a group of other friends for yet another “research” trip to Pamplona. Guess what? It ended in literal blood and tears.

23. He Had A Crush On A Femme Fatale

One of the participants in the trip was the beautiful, kittenish Mary Duff Stirling, who had recently divorced her husband and was on the rebound in a big way. Case in point: She had come to Pamplona with her lover Pat Guthrie, but she had also just been on a romantic vacation with another of Hemingway’s friends on the trip, the writer Harold Loeb.

Of course, with all that going on, Hemingway simply couldn’t resist Messy Mary, either…and the situation went nuclear.

24. He Got Into A Fight Over A Woman

Although Hemingway had brought his wife Hadley along to Pamplona, he sure didn’t spend any time with her. Instead, he mooned over Mary and griped with jealousy about both Guthrie and Loeb getting all of her attention. By the end of the week, Hemingway got into a dang fistfight with Loeb over the romantic rivalry. Still, the drama worked for him, and Hemingway came out of the vacation with a draft of the Sun Also Rises in his hands. Um, and then his marriage truly fell apart.

25. His Marriage Disintegrated

Hemingway was tiring of Hadley Richardson fast, and they both knew it. In December 1925, Hemingway was busy editing his manuscript when their family friend Pauline Pfeiffer joined them. Richardson’s spidey senses about the woman must have been tingling, because when Pfeiffer started offering writing advice, she kept trying to dissuade her husband from listening to her. Within weeks, Richardson found out her uneasy feeling was right.

26. He Backstabbed His Wife

In the midst of trying to get his novel published, Hemingway committed a vicious deception. While his wife Richardson was taking care of the children, Hemingway met up with Pauline Pfeiffer in Paris and, after what had obviously been a long period of flirtation, they went through with a full-blown affair at last. From then on, Hemingway was not subtle.

27. He Brought His Mistress On His Family Vacation

In 1926, Hemingway and Richardson were back in Pamplona again, but this time Hemingway had insisted that they bring his not-so-secret lover Pauline. Yeah, that was obvious to everyone involved, especially Hemingway’s wife. When they returned to Paris, she immediately asked for a separation. Still, Hemingway had one more knife to twist in poor Richardson’s side.

28. He Had A Quickie Wedding

Whether it was his first love Agnes’s cruelty replaying over and over in his head or Hemingway’s own natural coldness, the writer never could seem to exit a relationship gracefully. Indeed, when his divorce to Richardson finally officially went through in January of 1927, Hemingway married Pauline Pfeiffer just four months later. Ouch, dude.

Nonetheless, Hemingway wanted his second marriage to be a fresh start. Well, it began with a violent bang.

29. He Had A Nasty Bathroom Accident

As we’ll see, Hemingway’s life got more bizarre as it went on, but these strange occurrences started one infamous day in a Parisian bathroom. In 1928, Hemingway and his newly pregnant second wife were just about ready to move back to America when the writer, thinking he was pulling a flush chain on the toilet, accidentally brought down an entire skylight over his head while in the bathroom.

Yes, that sentence is hilarious—but the injuries Hemingway sustained most certainly weren’t. The mishap left him with an enormous forehead scar that mortified him, and which he often refused to discuss. As it happened, it was also an extremely bad omen for his stateside homecoming.

30. He Got Restless

While in America, Hemingway and Pfeiffer suffered through endless hardships. Although she ended up giving birth to a healthy boy named Patrick, her delivery was grueling, so much so that Hemingway even turned it into a passage in his next novel A Farewell to Arms. Moreover, the couple moved around from state to state constantly, exhausting everyone in their young family. In hindsight, though, everything was only leading up to the bombshell that was about to drop.

31. He Received Gut-Wrenching News

In 1928, Hemingway was just about to board a train from New York to Florida with his eldest son, and then he got the single worst news of his life up until then. He received a cable telling him that his father Clarence had completed suicide. Hemingway was devastated—but the full story of that day is even more heartbreaking.

32. He Made A Dark Premonition

Hemingway had some strange premonitions about his father’s sudden passing. For one, he had just sent Clarence a telegram reassuring him that he would always be there for him, but the message had come only minutes too late. Then, after accepting his father’s death, Hemingway reportedly announced, “I’ll probably go the same way.” As we know now, he was tragically right.

33. He Went Headlong Into War

After his father’s passing, Hemingway grew more restless than usual and flitted about on fishing and hunting trips with his various manly friends. In 1937, he finally found what he was looking for: Clear and present danger. When the Spanish Civil War cropped up, Hemingway flung himself into the action as a journalist. His wife, to no one’s surprise, was extremely hesitant to let him go traipsing into an open war zone. But she had other reasons to worry, too.

34. He Lusted After An Adventurer

While in Spain, Hemingway worked closely with ball-busting and respected reporter Martha Gelhorn, who he had actually met the year before. Now, alone for the first time and full of adrenaline, he and Martha started a tryst. For once in his life, Hemingway was head over heels for Martha because she didn’t “[cater] to him the way other women did.” This didn’t stop it from getting messy fast.

35. He Had A Destructive Romantic Pattern

By now, Hemingway had a pattern, and he didn’t spare his second wife Pauline from one second of indignity. Over the next months, he painfully and deliberately separated from her and their children to shack up with Gelhorn in Cuba. In 1940, when their divorce came through, he married Gelhorn quickly after, just like he had done the last time. But believe me when I say: Gelhorn quickly regretted her decision.

36. He Shunned His Wife

In 1944, Hemingway was again ambulance-chasing on the international stage, and went over to Europe to report on the nascent developments in WWII. What he did to his wife here is almost unspeakable. Already fed up with Gelhorn, Hemingway refused to get the ace reporter a press pass to take a plane ride over to visit. Instead, poor Martha went the long way across the Atlantic on a ship…filled with explosives. When she arrived, she couldn’t believe her eyes.

37. He Couldn’t Stay Faithful

As Martha took the slow boat to London, her husband was acting a darn fool, and it showed. Not only had he started skirt-chasing the beautiful Time writer Mary Welsh, who was nearly 10 years his junior, he had also managed to get into a severe car accident. He was actually in a hospital with a concussion when his wife arrived on British soil. Her response was ferocious.

38. His Wife Humiliated Him

To be fair to Martha, she really didn’t treat Hemingway like his other girls, and she sure as heck wasn’t going to stand for this tomfoolery. When Gelhorn visited her husband in the hospital, she didn’t have a shred of sympathy for him. Instead, she called him a bully and informed him they were “through, absolutely finished” before stomping off.

She stayed true to her promise. Hemingway virtually never saw her again, and Gelhorn won a divorce later that year. Of course, this only left Hemingway to his own devices. And those devices were…terrible.

39. He Tried Desperately To Be A Soldier

Hitting his mid-life crisis right on time, Hemingway became rabid about the idea of accompanying the troops on the Normandy landings in WWII. He was in for a big disappointment. Besides the fact he was, you know, a journalist and not a soldier, Hemingway was famous enough at this point that the leaders considered him “precious cargo.” They told him there was no way, no how he was going on shore. In response, Hemingway acted like a spoiled brat.

40. He Was A Rebel Leader

In July 1944, still seeking to recapture some of his glory days, the vaunted modernist writer Ernest Hemingway somehow managed to become the informal leader of a small guerrilla group of rebels in the French countryside. I know…WHAT? Apparently, though, everyone else was just as flabbergasted as us. Because as Hemingway’s “men” advanced toward Paris, he moved ever closer to his infamous punishment.

41. He Was A Geneva Criminal

Fun fact: Leading a group of military men when you’re JUST A JOURNALIST is, as it happens, in direct opposition of the Geneva Convention. Accordingly, the government came down hard on  Hemingway. Men brought up formal charges against the writer for his ridiculous show, and Hemingway only narrowly avoided a conviction after claiming that he just offered the troops “advice.” Somewhere back in the States, Martha Gelhorn just spit out her coffee.

42. His Fourth Marriage Came With Bad Omens

In 1946, Hemingway married his mistress Mary Welsh, and she became his fourth and final wife. But instead of happiness, he got a slew of tragedies. He suffered yet another car accident; Mary had an ectopic pregnancy, and his son Patrick also got into a crash and took months to recover. On top of these physical ailments, spiritual burdens also plagued him. Starting in 1939 and going on for nearly a decade, Hemingway lost friend after friend,  including F. Scott Fitzgerald in 1940 and James Joyce a year later.

By the end of the 1940s, Hemingway was walking wounded. And then came the ordeal that nearly broke him forever.

43. He Got Into A Plane Crash

In 1954, Hemingway and Mary were in Africa on yet another adventure trip; the writer had even bought his young wife a chartered flight over the Belgian-occupied Congo as a Christmas present. Sadly, it all went very wrong in the blink of an eye. While flying over to Murchison Falls to take photos, their plane hit a utility pole and started crashing to the ground. When the dust settled, horror reigned.

44. He Was A Wild Man

As Hemingway and his wife woke up in the midst of the crash, their hearts sank. Hemingway had a serious head injury, and they would later find out that Welsh had broken two of her ribs in the crash. But that wasn’t even the worst part. They were also in the middle of nowhere and had to trek out to get help a full day later. When they finally did reach their destination, the situation took another dark turn.

45. He Had The Worst Luck In History

Hemingway had never been the luckiest man in the world, but his next escapade takes the absolute cake. In a small town, Hemingway and Welsh chartered a second plane to fly them to the Ugandan city of Entebbe to get medical assistance. But just as they lifted off the ground, the plane burst into flames. Although Hemingway and his wife were still miraculously alive, the writer got a severe concussion and his head leaked cerebral fluid. Oh, and this story has one final twist.

46. He Died Before His Time

When Hemingway and Welsh arrived in Entebbe at long last, they came upon shocking news. Reporters had heard about the double crash and were currently printing out obituaries for the great American writer. Hemingway, lucky to be alive, spent the next few weeks recuperating in Entebbe and perusing what everyone was saying about him after his “death.” Still, although this is supposedly a happy ending, Hemingway’s final nightmare was around the corner.

47. He Was Ashamed Of His Nobel Prize

After Hemingway’s double plane crash in 1954, the writer was never the same again. Even when he won the Nobel Prize in Literature that same year for his masterful novella The Old Man and the Sea, the victory turned to ash in his mouth. While Hemingway called the book “the best I can write ever for all my life,” he couldn’t shake the feeling that he had won because the academy knew he had almost died.

48. His Demons Got Darker

The late 1950s were full of sadness and loneliness for Hemingway. Where before he had loosely controlled his alcoholism, now he was letting the substance control him. He was bedridden for nearly half a year thanks to his deteriorating state, but when doctors urged him to stop drinking, Hemingway only managed to quit for a short while. Before long, his health was having eerie effects on his mind.

49. His Mind Started To Go

In 1959, Hemingway experienced a terrifying event for the first time. Famous for his terse writing style, he had never had a problem turning in trim work….except all of a sudden, he couldn’t organize his thoughts properly. He had to ask his friend and editor A.E. Hotchner to help him pare down a series of articles on bullfighting for Life magazine, which Hemingway had “accidentally” made into a full-length novel.

Hotchner helped as best he could, but he was scared to see the previously gruff, powerful Hemingway “unusually hesitant, disorganized, and confused.” Still, no one could have predicted where it was heading.

50. His Genius Left Him

When he reached his 60s, Hemingway suddenly found himself with a case of writer’s block that he was never able to shake again. When aides asked him to contribute a sentence to a presentation volume for John F. Kennedy’s inauguration in 1961, he was unable to come up with a single word. His inability to write shook him so badly that he cried while telling a friend that “it just won’t come anymore.”

51. He Had A Breakdown

It wasn’t long before the press got wind of Hemingway’s odd, out-of-character behavior, and they reported that he was near death. Although Hemingway played it off as nothing, there was far too much truth to these rumors. He admitted to Welsh that he was on the verge of a breakdown, often refused to leave his home or his bed, and began to believe the government was watching him. Concerned for her husband, Mary Welsh made a decision she may have regretted.

52. He Went For Secret Treatments

Starting in 1960, Welsh sent Hemingway to the Mayo Clinic for treatment, but this treatment was top-secret—and harrowing. Hemingway checked in under a false name to retain anonymity, but reports released much later indicate he underwent as many as 15 electro-shock therapy treatments to help bring him back to some semblance of sanity. It didn’t work, and the consequences have rung throughout history.

53. He Retreated From The World

In January 1961, Hemingway finally left the Mayo Clinic. Yet according to one of his biographers, he was “released in ruins.” His mind in tatters and his attempt at getting “better” a colossal failure, Hemingway retreated to his farm in Ketchum, Idaho to try to recover in peace and quiet alongside Welsh and the rest of his family. To everyone’s deep dismay, that recovery never happened.

54. His Wife Stumbled On A Disturbing Scene

Although Hemingway’s end is now infamous, few people know that there were acute warning signs before. Just three months after his release from the Mayo Clinic, Welsh walked into her kitchen one morning to a blood-chilling sight: Hemingway casually holding a shotgun. With no idea how to handle it, Welsh called up Hemingway’s doctors again and put him through more electroshock therapy until the end of June 1961. No, this didn’t work.

55. He Ended His Own Life

When Hemingway went back to Ketchum again, he went right back to his plan. Just two days after getting back to the farm, he took out a “double-barreled shotgun that he had used so often it might have been a friend,” walked into his front foyer, and “quite deliberately” shot himself. Still, for all this icy clarity to that dark day, many mysteries remain…

56. He Had Chilling Similarities To His Father

The world mourned Hemingway’s passing, but the motives behind his end were even more tragic. According to people who knew the family, Hemingway’s bizarre behavior was quite like his father’s just before the elder Hemingway completed suicide. In fact, many thought there might be a genetic culprit behind both their ends. Decades later, modern researchers revealed the truth.

57. He Got A Horrible Diagnosis

In 1991, medical records from Hemingway’s time showed that doctors had diagnosed the writer with a disorder called hemochromatosis. This is where iron builds up in the body’s tissues and produces both physical and mental decline. Very likely, his father had it too, and Hemingway may have decided he couldn’t bear the thought of this kind of future for himself.

58. The FBI Watched Him

Perhaps most poignantly, despite his frail mental health near the end of his life, Hemingway’s paranoid thoughts were right about one thing. The government was watching him. The FBI had actually created a file on him all the way back in WWII, and, knowing that the writer liked to spend time in Cuba, J. Edgar Hoover even got an agent to watch the writer while he was in Havana.

59. He Punched A Famous Actor

Actor and director Orson Welles was just 22 when he first met Hemingway. The pair worked together on a Spanish Civil War documentary, and Welles decided to offer Hemingway a few suggestions on how to improve the script. Hemingway’s reaction was swift and brutal. The two ended up coming to blows and rolling around on the floor, although they ended the fight by opening a bottle of whiskey and drinking their way into a very odd friendship.

Although Welles always publicly claimed they were friends, behind the scenes he apparently loathed Hemingway’s “macho enthusiasms.” Plus, Hemingway didn’t like Welles much either. Maybe friends is an overstatement?

60. He Was A Soviet Spy

As it happens, Hemingway’s time as a guerrilla leader wasn’t even the stupidest thing he ever did. There is recent evidence that in 1941, while he was on assignment in China with Martha Gelhorn, the Soviets recruited Hemingway into espionage under the code name “Agent Argo.” The stupid part? Hemingway was a patently awful spy—if the rumors are true, he gave them no useful intelligence at all.

61. He Had A Bizarre Nickname

During the early 1920s, the young, burgeoning Hemingway received a strange nickname. Everyone, even his much older friends, started calling him “Papa.” Although no one could quite remember where the nickname came from (or at least they never told), the moniker stuck, and Hemingway signed missives “Papa” well into his later years.

62. Even His Writing Style Was Manly

Hemingway did most of his writing in his bedroom, but for the most part, not at the desk that dominated the space. His typewriter sat on top of a bookcase that he called his “work desk,” which he’d stand over for hours at a time while he wrote. On a good day, he would wear down seven pencils, and only moved to shift his weight from one leg to the other.

63. He Was A Thief

Of all the eclectic items that are on display in the Hemingway museum in Key West, the oddest might be the bar urinal that Hemingway converted into a garden fountain. Hemingway stole the urinal from his favorite bar, Sloppy Joe’s, after deciding that he’d “pissed away” so much money in that urinal that he owned it. That’s one way of looking at it, I guess.

64. He Fought A Group Of Sharks

One of Hemingway’s passions was fishing, and as a group of unsuspecting sharks learned, you don’t mess with his catch. While on a trip to the Bahamas in 1935, he used a Thompson submachine gun to open fire on a frenzy of sharks who were trying to steal the giant tuna he was after. However, the blood from the shots only served to stir up the sharks more, and they ended up winning the prize. Hemingway made up for the loss by setting a world record in 1938 and netting seven marlins in one day.

65. He Had A Hidden Trunk

In 1956, just a handful of years before his passing, an errant memory came to Hemingway, and ended up changing his legacy. He’d recalled that back in 1928, he had stored a bunch of old trunks in the Ritz hotel in Paris, and went back to retrieve them. Inside were old notebooks from his glory days in the French capital, and Hemingway shaped them into what would become his posthumous memoir A Moveable Feast.

66. He Was Tacky

If you’re keeping count, Hemingway married four times, each within a year of divorcing the previous wife. None of them can say he didn’t leave them with anything, however; each of them received a dedication in one of his novels. Call it a consolation prize?

67. He Didn’t Write His Most Famous Words

There’s a popular urban legend that Hemingway made a $10 bet that he could write a novel in six words. He then supposedly scrawled the phrase “For sale, Baby shoes, never worn” on a napkin and passed it around the table. The line has long been a favorite example of writing teachers, but it turns out it wasn’t really Hemingway’s. The real story is much stranger.

A similar line appeared in a newspaper as early as 1906, and there’s absolutely no proof that the bet ever happened or that Hemingway ever wrote or even talked about the micro-novel. A literary agent apparently concocted the tale in 1974, and the legend continued to spread. Even if he didn’t write it, it’s still a good example of minimalist writing.

68. He Was A Perfectionist

Hemingway re-wrote the last page of A Farewell to Arms 39 times before he was happy with the result. When an interviewer asked him what exactly was causing him trouble, Hemingway replied stoically, “Getting the words right.” OK then. Still, some of Hemingway’s friends and rivals thought they knew how to help him out…and they paid the price for their “generosity.”

69. He Had The Perfect Comeback

In what was a colossally stupid move, Hemingway’s ultimate frenemy F. Scott Fitzgerald once sent his buddy a 10-page letter giving him some advice. In it, Fitzgerald held court on which passage Hemingway should use to end A Farewell to Arms, since he couldn’t decide himself. Uh, Hemingway did not like this advice. Ever succinct, Hemingway sent back a note with just three words: “Kiss my a**!”

70. He Fell In Love With A Teenager

Hemingway had a notorious reputation for carousing and womanizing by the time he died, but there’s one excruciating part of his love life that still makes historians uncomfortable. In 1948, the nearly 50-year-old Hemingway—still very much married to Mary Welsh—fell in love with the teenager Adriana Ivancich while they were both staying in Venice, and carried on a years-long relationship with her.

In fact, he was so head over heels, he wrote the novel Across the River and into the Trees about their love…which he then published to almost universal derision.

Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40

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