Written By: Ben Cosgrove

That Ernest Hemingway was, for years, the most celebrated writer in America is hardly surprising. After all, if he had written nothing besides, say, The Sun Also Rises, the early collection, In Our Time, and the superlative “The Short Happy Life of Francis Macomber,” he would still be an indispensable American writer. The preposterous literary myth that Hemingway himself created and nurtured, meanwhile—that of the brawling, hard-drinking, thrill-seeking sportsman who is also an uncompromising, soulful artist—ensured that generations of writers would not merely revere him, but (often to their abiding detriment) would also try to emulate him.

Incredibly, one of Hemingway’s most highly regarded novels, the short masterpiece, The Old Man and the Sea, was first published, in its entirety, in a single issue of LIFE magazine in September 1952.

At the time, Hemingway was—if we might employ an apt metaphor for a man who fairly worshiped machismo—the heavyweight champ of American letters. Even if his productivity had waned, and even if the searing brilliance of his early years had, by 1952, been reduced to an occasional flare of the old genius, “Papa” was still a cultural force to be reckoned with.

(A mere two years before, John O’Hara, in a New York Times review of the novel, Across the River and Into the Trees, had gone a bit overboard, calling Hemingway “the most important author living today, the outstanding author since the death of Shakespeare.” But such was the shadow he cast.)

The issue of LIFE featuring Old Man and the Sea was an enormous success, selling millions of newsstand copies in a matter of days. The novel itself earned Hemingway his first and only Pulitzer Prize for fiction, and remains among his most widely read works.

And yet, by the early 1950s Hemingway’s private world was one increasingly defined not by protean artistic achievements, but by rivers of booze; bewilderment at his own diminishing powers as a writer; depression and even rage at his failing, once-indomitable health. The larger-than-life figure who prized “grace under pressure” above all other attributes was besieged; in less than a decade, his demons would drive him to suicide by shotgun.

All of this helps explain why, when LIFE’s Alfred Eisenstaedt went to Cuba to photograph Hemingway for the September 1952 issue, he encountered not a gracious, if perhaps prickly, fellow artist and man of letters, but a thoroughly disagreeable, paranoid, booze-sodden lunatic.

Eisenstaedt was able, eventually, to capture a few usable images of the middle-aged man who was soon be awarded the Nobel Prize for Literature. His cover photo of Hemingway, in fact, is something of a classic: a riveting portrait of a no-longer-young, still-formidable literary lion.

But the experience of trying to photograph the 52-year-old writer, as Eisenstaedt recalled years later in an interview with historian Alex Groner, was a stressful and at times even frightening misadventure.

Hemingway, Eisenstaedt wonderingly noted, drank from the moment he awoke until the time he went to bed, with a lackey constantly plying him with booze; obsessed over his virility (sometimes literally pounding his chest, “like King Kong,” to illustrate that, while perhaps diminished, he was still a man to whom attention must be paid); erupted into violent rages over minor slights, both real and imagined; rarely spoke a sentence, to anyone, that wasn’t peppered with obscenities; and generally behaved like a buffoon.

Words and phrases that crop up repeatedly in Eisenstaedt’s reminiscences include “crazy,” “berserk,” “wild,” “insulting,” “drunk,” and “blue in the face.” Eisenstaedt found very few moments when he could take or when Hemingway would allow him to take usable photos. More than once, the gregarious, easy-going Eisie, who by all accounts got along famously with virtually everyone he met, went off by himself to photograph quieter scenes on the island, hoping the writer might calm down enough so that he might make a few worthwhile pictures.

“He was,” Eisenstaedt once said of Hemingway, “the most difficult man I ever photographed.” Coming from a man who was a professional photographer across seven decades—someone who photographed presidents, emperors, socially awkward scientists, testy athletes, egomaniac actors, insecure actresses and once, famously, a scowling and goblin-like Nazi minister of propaganda, Joseph Goebbels— that bald assertion about Hemingway is striking, and sadly revealing. And it’s especially sad in light of the effort that Eisenstaedt evidently put into trying to like Hemingway.

Ernest Hemingway was a major writer. Not everything he wrote was great; but some of what he wrote was as good as anything ever written by an American, and a handful of his works are, by common assent, vital and groundbreaking landmarks in world literature.

This gallery serves as both a tribute to Hemingway’s achievements, and a reminder of the haunting truth that when they fall, great men fall very, very far indeed.

Liz Ronk edited this gallery for LIFE.com. Follow her on Twitter @lizabethronk.

 

Ernest Hemingway in Cuba August 1952

Ernest Hemingway in Cuba, August 1952

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

A contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

A contact sheet of Alfred Eisenstaedt’s pictures of Ernest Hemingway in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

Ernest Hemingway chats with fellow patrons at a cafe he enjoyed frequenting in Cuba, 1952.

Ernest Hemingway chatted with fellow patrons at a cafe he enjoyed frequenting in Cuba, 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

A contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

A contact sheet of Alfred Eisenstaedt’s pictures of Ernest Hemingway in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

Ernest Hemingway at home in Cuba, August 1952.

Ernest Hemingway at home in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

An image from a contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

An image from a contact sheet of Alfred Eisenstaedt’s pictures of Ernest Hemingway in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

An image from a contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

An image from a contact sheet of Alfred Eisenstaedt’s pictures of Ernest Hemingway in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

A contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

Ernest Hemingway in Cuba, August 1952

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

Cojimar, a Cuban fishing village and the inspiration for the village in Hemingway's novel, The Old Man and the Sea, August 1952.

Cojimar, in Cuba, provided the inspiration for the fishing village in Hemingway’s novel, The Old Man and the Sea, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

An image from a contact sheet of Alfred Eisenstaedt's pictures of Ernest Hemingway in Cuba, August 1952.

An image from a contact sheet of Alfred Eisenstaedt’s pictures of Ernest Hemingway in Cuba, August 1952.

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

Ernest Hemingway in Cuba, August 1952.

Ernest Hemingway in Cuba, August 1952

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

09_01_52.jpg

LIFE Magazine cover, September 1, 1952

Alfred Eisenstaedt The LIFE Picture Collection/Getty Images

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