Clark Collis
April 26, 2013 AT 04:00 AM EDT

F. Scott Fitzgerald is one of the most celebrated novelists of all time, but his days writing and rewriting screenplays — including the one for Gone With the Wind — were far less fruitful. As an acquaintance of his, Some Like It Hot director Billy Wilder, once said, ”He made me think of a great sculptor who was hired to do a plumbing job. He did not know how to connect the f—ing pipes.”

Wilder’s view is shared by director Baz Luhrmann, though he prefers a different analogy. ”You put a brilliant dancer — a superstar — in the chorus, and they stick out,” he says. ”They’re hopeless, terrible. They can’t do it.” Luhrmann knows what he’s talking about, Fitzgerald-wise. On May 10, Warner Bros. will release the fourth big-screen adaptation of Fitzgerald’s classic novel The Great Gatsby. The 3-D film is directed and co-written by Luhrmann and stars Leonardo DiCaprio as the title character, a mysterious millionaire who attempts to lure his now-married ex-girlfriend Daisy (Carey Mulligan) back into his life by hosting lavish parties at a Long Island mansion. If the film’s a hit, it will be a rare happy chapter in the story of Fitzgerald and Hollywood — a tale marked mostly by disappointment and disaster.

Fitzgerald, who was born in St. Paul in 1896, loved the movies. ”He was there almost at the infancy of the industry,” says James L.W. West III, professor of English at Penn State and a Fitzgerald scholar whom Luhrmann used as a historical expert on his film. ”He wrote stories about Hollywood and was very interested in the possibilities of cinema.” Shortly after the career-making 1920 publication of his debut novel, This Side of Paradise, the author revealed in an interview that he was a fan of Charlie Chaplin while admitting it might be a problem to ”mold my stuff into the conventional movie form with its creaky mid-Victorian sugar.” However, in the early ’20s, Fitzgerald’s short stories ”Head and Shoulders” and ”The Offshore Pirate” were adapted for the screen, as was his second novel, 1922’s The Beautiful and Damned.

Fitzgerald published The Great Gatsby in 1925, and though the book didn’t sell nearly as well as its predecessors, an adaptation hit theaters in 1926. The next year, the author and his wife, Zelda, headed for Hollywood so he could write an original screenplay called Lipstick for the studio First National. The company subsequently canceled the project, but the famously hard-partying couple left an impression during their stay in L.A., on one occasion gathering together all the purses they could find at a party and cooking them in tomato sauce. Four years later, Fitzgerald was back to adapt another author’s novel for MGM. This time, he was desperate for cash and alone, the troubled Zelda having been hospitalized following a nervous breakdown. The writer caused another scene at a party, drunkenly crooning a song about a dog at an event held at the house of MGM boss Irving Thalberg. He was fired a week later.

In 1937 Fitzgerald returned to L.A. yet again after a director friend persuaded MGM to offer him another contract. His fourth novel, 1934’s Tender Is the Night, had flopped, and the author was largely forgotten and deeply in debt with bills piling up for Zelda’s treatment and their daughter Scottie’s education. ”The first time I saw Scott he was in the commissary sitting alone at a table,” It’s a Wonderful Life screenwriter Frances Goodrich would later tell Aaron Latham, author of the 1971 book Crazy Sundays: F. Scott Fitzgerald in Hollywood*. ”He looked as if he were seeing hell opening up before him. I never forgot that tormented face.”

Fitzgerald faced torments aplenty during his third sojourn in the dream factory. He received his sole screenwriting credit on 1938’s Three Comrades, a film extensively rewritten by producer Joseph L. Mankiewicz (whom the author privately referred to as ”Monkeybitch”). Fitzgerald spent the rest of his time sweating away on projects that never arrived on the screen — including a proposed Joan Crawford vehicle called Infidelity — or for which he failed to receive a credit, such as Gone With the Wind. He recalled toiling on GWTW as a particularly bizarre experience given producer David O. Selznick’s insistence that any dialogue he added should come from Margaret Mitchell’s original potboiler. ”One had to thumb through as if it were Scripture,” Fitzgerald later wrote, ”and check out phrases of hers which would cover the situation!”

Fitzgerald’s lack of success failed to correct the assumption among many that this faded Jazz Age icon had passed away. One day a producer named Walter Wanger called the young writer Budd Schulberg into his office and asked how he would feel about Fitzgerald helping him on his screenplay Winter Carnival. ”Isn’t Scott Fitzgerald dead?” Schulberg asked. ”On the contrary,” replied the producer, ”he’s in the next office reading your script.” Fitzgerald was fired from the film after he turned an East Coast research trip with his new collaborator into an extended drinking bender. He hoped to weave gold out of his Hollywood experiences in the form of a novel, The Last Tycoon, about a Thalbergesque studio chief. Alas, in December 1940, he died of a heart attack, with The Last Tycoon unfinished and his Hollywood dreams unfulfilled.

It’s been 39 years since Jay Gatsby last sauntered across movie screens, in a Robert Redford-starring adaptation that New York Times reviewer Vincent Canby found ”as lifeless as a body that’s been too long at the bottom of a swimming pool.” Professor West argues that screenwriters have been ”hypnotized” by the writer’s prose with negative results: ”It doesn’t seem to live on the screen in quite the same way.” Luhrmann and his co-screenwriter Craig Pearce have stayed true to the book in many ways, but theirs is a far more visually energetic affair than previous adaptations and is certainly the first to boast a hip-hop-fueled soundtrack overseen by Jay-Z. ”I have tried to be not so much faithful to a revered text,” says Luhrmann, ”but to reproduce what it felt like to read a book of incredible immediacy in 1925.”

Five days after its U.S. release, Luhrmann’s Gatsby will open the Cannes Film Festival. That in itself qualifies as something of a happy ending for the sorry tale of Fitzgerald’s relationship with the movies, albeit one with a bleak twist. The peripatetic author actually wrote part of The Great Gatsby on the French Riviera not far from where the film will be screened, while a neglected Zelda embarked on a flirtation with a young French pilot, which many believe turned sexual. ”The ‘happy ending’ is that the film, I hope, comes to life in 3-D on the very beach where his wife was having an affair,” says Luhrmann. ”I don’t know what to make of that, except: Isn’t the circle of life a funny thing?” Funny. And appropriately Fitzgeraldian.

*An earlier version of this article inadvertently left off the full title of Latham’s novel.

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