WEST HOLLYWOOD, Calif. — Meltdowns are not Matt Bomer’s style, not even remotely, but he would have been due one in mid-March.
It was late afternoon, and Mr. Bomer had been at work since 5 a.m. on the set of “The Last Tycoon,” the latest adaptation of F. Scott Fitzgerald’s unfinished novel about Old Hollywood. Mr. Bomer, as Monroe Stahr, a gifted young movie executive, had started the day with a difficult monologue about death and moved on to a hot-and-heavy love scene. A confrontational third scene, performed with Kelsey Grammer (as Stahr’s thunderhead boss, Pat Brady), had left Mr. Bomer emotionally raw.
Then I arrived to ask him jagged questions. For more than 90 years, Hollywood has been trying and failing to pull off the perfect Fitzgerald adaptation. Why couldn’t anyone seem to get it right? What would keep this “Last Tycoon,” arriving on Amazon Prime on Friday, July 28, from becoming another sad example?
“Making a great television show is hard enough,” Mr. Bomer said carefully. “To also tackle F. Scott — whoa. But when you have brilliant people guiding you, people like Billy, you trust their vision and go for it.”
That would be Billy Ray, the Oscar-nominated screenwriter (“Captain Phillips”) leading this nine-episode incarnation of “The Last Tycoon,” which Fitzgerald left unfinished upon his death in 1940. Mr. Ray, along with another writer-producer, Christopher Keyser, have envisioned a series of uncommon ambition. Forget Fitzgerald for a moment. Set in 1930s Hollywood, “The Last Tycoon” wants to be Amazon’s version of “Mad Men,” a meticulous period drama that influences pop culture and mesmerizes Emmy voters. More than 40 “Mad Men” crew members — makeup artists, directors, dialect coaches, costume designers, set dressers — are now working on the new show.
Adding a degree of difficulty, “The Last Tycoon” will serve as a vehicle for commentary about modern-day Hollywood and America as a whole. “All these things that are coming to a head right now in our country — immigrants, sexism, the generational clash — are really big elements in our show,” Mr. Bomer said. “There are so many American ideals that Fitzgerald was wrestling with and that we’re still struggling to perfect.”
It all sounds fascinating. But cracking Fitzgerald would be a feat unto itself.
“No one has ever really managed to find the visual equivalent of Fitzgerald’s writing,” said Jeanine Basinger, the author of “The Star Machine” and the founder of Wesleyan University’s film studies program. “It always feels hollow. The soul is gone.”
Of “The Last Tycoon” in particular, she added, “It is awfully hard to film Hollywood — to make it look authentic.”
Fitzgerald’s work has served as the source for at least 20 movies and television shows, and it is hard to name one that truly sizzled. His short stories, in part because they are not as widely known, giving screenwriters more license to extrapolate, have been the least problematic. A PBS adaptation of “Bernice Bobs Her Hair,” about an introverted woman confronting the Jazz Age, drew praise in 1976 for Shelley Duvall’s charming performance. “The Curious Case of Benjamin Button,” the 2008 film starring Brad Pitt as a man aging in reverse, was considered a feat in visual effects.
But movies based on his books have mostly been considered crimes against literature (and sometimes retinas). When “The Beautiful and the Damned,” a Manhattan morality tale, was adapted by Warner Bros. in 1922, Fitzgerald called it “the worst movie I’ve ever seen in my life — cheap, vulgar, ill-constructed and shoddy.” “Tender Is the Night” lost its psychological underpinnings when 20th Century Fox turned Fitzgerald’s complex tale of interlocking relationships into a vehicle for Jennifer Jones in 1962; the film’s director, Henry King, never worked again.
Of the various “Great Gatsby” films, the 1974 version starring Robert Redford is considered by many to be the most watchable, which is saying something. Reviewing that movie in The New York Times, Vincent Canby called it “as lifeless as a body that’s been too long at the bottom of a swimming pool.” Critics were (a bit) kinder to the most recent “Great Gatsby,” directed by Baz Luhrmann in 2013 and starring Leonardo DiCaprio. A. O. Scott, the co-chief movie critic for The Times, called it a “splashy, trashy opera” that was “eminently enjoyable.” But Mr. Luhrmann’s glossy approach horrified some purists. A. Scott Berg, a Pulitzer Prize-winning author and Fitzgerald authority, assessed Mr. Luhrmann’s film this way: “Don’t get me started on that.”
Mr. Berg, whose books include “Goldwyn: A Biography,” about the movie mogul Samuel Goldwyn, is a consulting producer of Amazon’s “The Last Tycoon,” and he vetted every script. Hollywood’s challenges with Fitzgerald, he explained, start with his words.
“What makes his work so intoxicating is the writing — ‘So we beat on, boats against the current, borne back ceaselessly into the past,’” Mr. Berg said, quoting the last line from “The Great Gatsby.” “But you can’t film language. You can use narration, of course. But narration is usually something pasted on a film when the visual storytelling isn’t working.”
Rewrite too much, and Fitzgeraldophiles have a fit. But his novels are generally not structured for film. (“Tender Is the Night,” for one, uses shifting perspectives and moves forward and backward in time.) So screenwriters have no choice. Novels heavier on plot — works by Charles Dickens, for example — lend themselves more easily to adaptation, Mr. Berg noted. “Fitzgerald, on the other hand, fought metaphorically in his writing,” he said.
When Fitzgerald died, “The Last Tycoon” was half-finished, the incomplete story of two men, partners yet rivals, who keep a fictional film studio afloat as labor unions form and financing ebbs and flows. At the same time, the emotionally wounded younger executive, played by Mr. Bomer (“The Normal Heart”), struggles to move on after the death of his movie star wife.
It was published only after the critic Edmund Wilson completed a version based on notes left behind. The best-known adaptation, directed by Elia Kazan and starring Robert De Niro, was a disaster in 1976. “So enervated that it’s like a vampire movie after the vampires have left,” the critic Pauline Kael wrote at the time in The New Yorker.
But the creative ensemble behind the new “Last Tycoon” saw the unfinished aspect of the book as an opening.
“Keep the icons from the novel — the Shiva head, the two-dimes-and-a-matchbox speech — but polish them up, move things around, explore characters in deeper ways,” Mr. Berg said. “There could be 50 episodes here if done correctly.” He added, “What was put together as a book was extrapolated itself, so let’s extrapolate from there.”
“The Last Tycoon” is a roman à clef. Fitzgerald had returned to Los Angeles in 1937 to give screenwriting another stab. He had bills to pay after the commercial failure of “Tender Is the Night,” published in 1934. As he typed in an office on the Metro-Goldwyn-Mayer lot, he began to hear tales of the interaction between Irving Thalberg, a next-generation film executive seen as a “boy wonder” for his ability to meld art and commerce, and the grandest of studio grand pooh-bahs, Louis B. Mayer.
His observations became “The Last Tycoon.” Joining the men at the forefront of the story is the plucky Celia (Lily Collins), whose father (Mr. Grammer) runs the studio.
“There is just so much going on with Celia — steadfast, tenacious, passionate, naïve but saucy,” Ms. Collins told me between takes. “I think fleshing Celia out was a little bit of how Billy and Chris solved the puzzle, and, you know, made this story into something that can last multiple seasons.”
For his part, Mr. Ray said he was not overly worried about solving anything. Rather, he saw Fitzgerald’s novel as a doorway — to period and setting (as exacting with 1930s Hollywood as “Mad Men” was with 1960s Manhattan) and the movie business, past and present.
“Who has power, what do they do to get it, what do they do when they’ve lost it?” Mr. Ray said. “What are the trades, compromises and deals that you’d make to get your movie made? No difference between 1936 and 2017. None.”
Mr. Ray pointed to a plotline in the pilot, which has been available on Amazon since last summer, about how Mr. Bomer’s character wants to make a movie but can’t because the German government might find the story objectionable. In the 1930s, Germany was a huge box-office market.
“Those exact same conversations are being had about China right now all over Hollywood,” Mr. Ray said. “It’s too big of a market to offend.”
He added, “This is a world — then, now — where creative impulses are systematically tempered if not squashed by the system.” He insisted, however, that the companies behind “The Last Tycoon,” which include Sony Pictures Television in addition to Amazon, had made requests that only improved his show. “They were interested in the glamour and the romance, and they were right,” Mr. Ray said.
(Amazon executives do seem to have a fondness for the period — and Fitzgerald. In January, the streaming service unveiled the series “Z: The Beginning of Everything,” starring Christina Ricci as a fictionalized version of Fitzgerald’s wife, Zelda.)
Mr. Ray’s point about the unchanging nature of the movie business came into sharp relief during my visit to “The Last Tycoon” set. The show had taken over Stage 4 on a compact West Hollywood lot known for hosting productions like “Some Like It Hot” (1959) and “Fiddler on the Roof” (1971). Over the decades, Charlie Chaplin, Howard Hughes, Frank Sinatra and Francis Ford Coppola used it as home base.
Mr. Grammer took a rest on a bench outside the sound stage to chat with me. (“My character has a lot of self-knowledge, but he’s also a bit of a brat,” he said. “All of a sudden, he’s slamming into an emotion he didn’t see coming.”) Inside Stage 4, where the air smelled of paint and wood, Mr. Bomer was marveling over the meticulous production design by Patrizia von Brandenstein, who won an Oscar for “Amadeus” and put John Travolta in his white “Saturday Night Fever” suit. Indeed, there did not seem to be a matchstick out of place in the palatial, wood-paneled office belonging to Mr. Grammer’s studio boss. A monumental carved mahogany desk sat on a platform at the end of the room. Flanked by torchères and ferns and dramatically decorated with an ormolu-mounted encrier, the desk — sitting in front of a stained-glass window — was more throne than anything.
The same scene could well have unfolded in 1936.
Filming soon resumed, with Mr. Bomer and Mr. Grammer performing that confrontational scene. Their fictional studio had fallen on hard times and borrowed money from a cutthroat competitor. Mr. Grammer’s character wanted to pay back the loan by requiring all employees to take a 30 percent pay cut. And he wanted his popular production chief to break the news.
“You can’t treat people this way and expect them to do good work!” Mr. Bomer shouted.
“No,” Mr. Grammer replied. “But you can.”
The director called cut.
A swarm of crew members came out of hiding to fuss over various details. One woman adjusted Mr. Grammer’s pocket square ever so slightly, and a man holding a rolled-up script gave a suggestion to Mr. Bomer. Perhaps add a touch more smoke to the air, someone suggested. (It filters the light in a pretty period way.)
“Let’s try it again,” the director said.
After all, the pressure was on. This time, Fitzgerald was going to be done right.