How Amazon’s ‘The Last Tycoon’ Explores the Costs and Reality of the American Dream

Creator Billy Ray and executive producer Chris Keyser talk about their casting luck and plans for future seasons.
Courtesy of Amazon Studios
Matt Bomer in 'The Last Tycoon'

Amazon’s newest drama was born in the heart of the Lost Generation, hidden between the pages of F. Scott Fitzgerald’s last, unfinished novel.

The Last Tycoon takes place in the late 1930s, finishing an untold story of the Golden Age of Hollywood amid the Great Depression and the rise of the Nazi regime across the Atlantic, which threaten the American freedom Hollywood reaped the benefits of in the past.

“The story that we’re trying to tell is both the gap between the dream of Hollywood and the reality of Hollywood and why that dream has such an irresistible and intoxicating grasp on us,” Tycoon creator Billy Ray tells The Hollywood Reporter. “We were sort of past Fitzgerald’s novel by the time we were done with the pilot."

Ray, the Oscar-nominated writer of Captain Phillips and a longtime movie screenwriter, and fellow executive producer Chris Keyser hope their series both conveys the struggles of Hollywood in 1936 and brings them into the present, where those issues still remain.

“Is it really true that we live in a country in which we all have the chance to become something other than who we are?” Keyser asks. “That’s not really clear anymore and the question of all of that is very critical.”

“The American dream both works and has its costs," he adds. "[The characters] are all putting on clothes and trying to be somebody else as they attempt to make it in America. That’s really romantic, obviously, but at the same time, that’s really destructive.”

The show is not solely driven by those questions, though. “It’s Fitzgerald. It’s '30s Hollywood. It’s irresistibly juicy,” Ray says of the series, which features plenty of plot twists and forbidden love triangles.

“It is a beautiful, shocking, funny, romantic, slightly dangerous, compelling, operatic, intimate, American story that says something about who we are as a people in a timeless way,” Ray promises of the series, the first season of which starts streaming on Amazon on Friday (July 28).

The Last Tycoon stars Kelsey Grammer, Matt Bomer and Lily Collins alongside castmembers Rosemarie DeWitt, Dominique McElligott and Iddo Goldberg. And many of the scenes were written for this cast specifically.

“Every actor that we wanted said yes,” Ray says, speaking of his fortune to have been able to get the all-star cast he dreamed of. “It starts to feel like a party people want to be at and we benefited from that hugely."

The team spoke highly of their experience with the cast while in production, with Ray calling it the “most fun he’s ever had in his career.”

And Ray and Keyser hope to keep the party going, with plans for as many as five seasons worth of stories.

“The last episode [of the first season] ends in a way that is no way closed-ended and there are things  you get answers to some questions  but there are more things left unanswered," Ray says. "It was written entirely in anticipation of our hoped-for second season."

Keyser adds, “We have plans for the last scene of the last episode of the last season, which we are planning to be season five, we just need that opportunity."

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