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The Art of THE DEAL

Vanity Fair US

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The Hollywood Issue 2025

What it took to get my movie about Donald Trump and Roy Cohn in front of an audience

- Gabriel Sherman

The Art of THE DEAL

Sebastian Stan, who plays Donald Trump in The Apprentice, was one of the few Hollywood actors interested in the role.

ON THE NIGHT of May 20, I stood in the storied Auditorium Louis Lumière at Cannes and listened as more than 2,000 people in black tie gave an eight-minute standing ovation for the film I wrote: The Apprentice. The movie is a Frankenstein’s monster origin story about Donald Trump, played by Sebastian Stan in prosthetics and a golden toupee. It follows Trump as he rises in Manhattan real estate under the tutelage of lawyer turned fixer Roy Cohn, played with dead-eyed menace by Jeremy Strong. One scene depicts Trump sexually assaulting his first wife, Ivana. Others showed Trump getting liposuction, undergoing scalp reduction surgery, and popping amphetamine diet pills—details reported in Harry Hurt III’s 1993 Trump biography, Lost Tycoon. (Trump denied the claims at the time.)

During the after-party, with views of oligarch-owned yachts anchored in the harbor, I began getting alerts on my phone: Trump announced he planned to sue to block the movie’s release. Campaign spokesperson Steven Cheung called the movie “malicious defamation” and “election interference by Hollywood elites.” I had a pit in my stomach, but I also felt strangely validated. Trump’s legal threat followed the first rule Cohn elucidates in the movie: Attack, attack, attack.

Two days later, Trump’s lawyers sent the film’s director, Ali Abbasi, and me cease-and-desist letters that warned Hollywood companies against distributing the movie.

I hoped the controversy and buzz would translate into a deal. But by the time I flew home, no Hollywood company had made an offer to release the movie in the United States.

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