The Man Behind The Great Gatsby, F. Scott Fitzgerald, and his Friendship with Ernest Hemingway

After meeting Ernest Hemingway in 1925, F. Scott Fitzgerald wrote a letter to his editor at Scribners advising: “I’d look him up right away. He’s the real thing.” Thus began an unlikely friendship between two of the greatest writers in American history. Though complicated, short-lived, and ultimately resentful, the relationship between Ernest Hemingway and F. Scott Fitzgerald helped expose Americans to yet another master of the Lost Generation of literature.

At first glance, their friendship might not seem all that unusual. Both were incredibly talented alcoholic writers who happened to bump into each other in Paris during the 1920’s (when it was the cheap place to be, if you can imagine that). In terms of shared traits, however, this is about as far as it goes.

As Hemingway tells it, F. Scott Fitzgerald was a “charming and endearing” but had a reputation as an overeager socialite. On a more awkward note, Fitzgerald also talked way too casually about the intimate details of people’s lives. (During their first conversation, for example, Fitzgerald asked if Hemingway had had premarital sex with his wife, which isn’t exactly the stuff of cocktail parties.) Later in life, Hemingway wrote scathingly of Fitzgerald, saying that the only thing he ever respected about the guy was his talent – which he’d largely wasted. Ouch.

Ernest Hemingway, in contrast, was a bearlike man’s man with a serious chip on his shoulder for having been repeatedly dressed like a girl by his mother when he was a child. (No, we’re not making this up.) As his treatment of Fitzgerald would seem to suggest, Hemingway was also a bit reactionary when things didn’t turn out the way he’d hoped. His pursuits included traveling, punching people, killing large animals, and living dangerously.

For a while, the two made the most of their differences by bumming around Paris, swapping stories, and playing games like let-Fitzgerald-start-a-bar-fight-so-that-Hemingway-can-finish-it. (We aren’t making this up, either.) The friendship had professional benefits as well. Fresh off his Great Gatsby success, Fitzgerald nurtured Hemingway’s writing and helped bring him into the literary spotlight. (And with a reputation for ingratiating himself to the successful, suffice it to say that Hemingway didn’t stop him.)

A big obstacle to their friendship, however, was the fact that Hemingway and Fitzgerald’s wife, Zelda, absolutely couldn’t stand each other. Zelda had zero tolerance for Hemingway’s machismo, which she felt was totally contrived. (Knowing how to hit him where it hurts, she later accused Hemingway of having an affair with her husband.) In turn, Hemingway thought Zelda was “a crazy” whose neediness drove Scott to drinking. To make matters worse, Fitzgerald’s popularity dwindled as Hemingway’s grew – to say nothing of their respective financial situations. It was only a matter of time before the strange relationship strained under the pressure.

In 1929, after proofreading A Farewell to Arms, Fitzgerald sent Hemingway a thoughtful ten-page letter of praise, critique, and suggestions, particularly focusing on how to improve the closing lines of the novel. Hemingway’s response? A now-famous “Kiss my ass.” Clearly, the apprentice felt he’d outgrown the master.

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