Gabriel Sherman has been at the forefront of reporting on the rise of the right-wing media. His coverage of the Murdoch family infighting makes “Succession” look like a documentary, and his chronicling of the rise of Fox News, coupled with reporting that brought the fall of its architect Roger Ailes, is the stuff of Greek tragedy.
In addition to being a well-sourced reporter, Sherman is a writer with a knack for narrative, with a keen eye for how human frailty mixed with greed and power have created such destructive forces on our society. Therefore, it’s not surprising that in recent years Sherman started to develop non-fiction scripted projects in Hollywood, most notably the Russell Crowe-led adaptation of his Roger Ailes biography into the Showtime limited series “The Loudest Voice.”
Sherman’s latest project to hit the big screen is “The Apprentice,” which opens in theaters October 11. The independently financed film, directed by Ali Abbasi (“Border,” “Holy Spider”), based on a script by Sherman, is the story of how a young, ambitious Donald Trump (Sebastian Stan) is mentored by the cutthroat Roy Cohn (Jeremy Strong).
The film is set in the 1970s and ’80s, and is shot like the gritty New York-based movies of the era. It serves as a Trump origin story of sorts, as we watch the still malleable, almost innocent, pre-fame Trump learn his take-no-prisoners philosophy and bare-knuckle tactics that will be all-too-familiar for an American audience that has had our politics dominated by Trump for the last decade.
After spending much of his professional life chronicling how the right wing wields its power, you would think Sherman would have a clear-eyed view going into “The Apprentice” of the obstacles he would face in getting the film into theaters. But as Sherman revealed this week in an essay he wrote for Vanity Fair, his difficult journey from premiering the film at the Cannes Film Festival in May to theaters tomorrow has been his “dark night of the soul moment.”
Sherman is still not quite sure what transpired during his four-month fight to find distribution while under the threats from Trump of a lawsuit, an investor who blocked the sale of the film, but the experience has left him reflective on the risk-averse state of Hollywood in 2024, an issue he dug into the interview below, as he walked IndieWire through his experience of getting “The Apprentice” to the big screen.
IndieWire: Let’s go back to May, your film’s just premiered at Cannes, and your phone’s blowing up, Trump is threatening to sue. As someone who has followed him and has made this film about how Roy Cohn taught Trump, “attack, attack, attack,” you had to be expecting that, right?
Gabriel Sherman: I mean, yes. I was obviously feeling two things at the same time. First, I was obviously stressed out because I knew that a threat of a lawsuit might complicate the ability for us to sell the film. But secondly, I was also kind of chuckling because it was a case of life imitating art. Trump was just following the playbook that Roy Cohn, played by Jeremy Strong, had spent the previous two hours explaining in the movie.
I was frankly surprised that we didn’t hear anything from Trump prior to Cannes. It had been in the press for years that I was developing this movie and there had been tabloid photos of Sebastian Stan, who plays Trump in the film. And I was expecting, honestly, that Trump would have threatened to sue earlier.
I get the sense you were a little surprised, though, by how distributors reacted, correct?
Yes, I was. I wrote this in my Vanity Fair piece, it’s been a lot for me to really process to see how risk adverse the big Hollywood companies have become. In 2019, I adapted my Roger Ailes biography into a limited series at Showtime starring Russell Crowe and Naomi Watts and Sienna Miller. The main subject of the film, Roger Ailes, had died prior to filming the series, but the series was a very dark look at Fox News, which is a major force in our present-day culture and Showtime distributed the series and was fully behind us.
So, from 2019 to 2024, to see Hollywood have no interest in tackling a controversial present-day story like Donald Trump, I think, was a sign the industry is just in a much more timid place than it was even five years ago. So I was surprised and disappointed by that. I think post-COVID, post-strikes, post-Netflix-correction, I think the financial difficulties of the industry have made them creatively a lot more cautious.
Editor’s note / spoiler alert: “The Apprentice depicts Trump sexually assaulting his first wife, Ivana (Maria Bakalova), which is a dramatization based on allegations Ivana made in a deposition during her 1990 divorce. 25-years later, when Trump went to run for President, Ivana recanted, clarifying when she had used the word “rape” under oath, she did not mean Trump assaulted her in a “criminal sense,” only that she felt violated. The other controversial elements of the film show Trump getting liposuction, undergoing scalp reduction surgery, and taking amphetamine diet pills, all details previously reported in Harry Hurt III’s 1993 Trump biography, “Lost Tycoon.” Trump has denied all of these claims.
Well, let’s talk about that, if we were to make a comparison between Hollywood to your reporting for publications like Vanity Fair, I’m sure there’s pushback with some of what you write, but isn’t this a case with what this film is showing that you are on such safe ground, because of previous reporting regarding the divorce papers, the rape accusation, and what was in “Lost Tycoon,” like the liposuction? Wouldn’t publications feel they were on safe, legal ground in terms of a lawsuit?
Yeah, I mean there’s nothing in this film that has not been well documented on the historical record for years. When I turned in the script when we got this shooting script ready for production, I had to annotate the script for our lawyers, and I had to go through, just in the same way I would for a Vanity Fair article, I had to annotate every fact and show where I got it, and if I dramatized a fact, show the creative basis for how I would have dramatized a certain scene. So there’s nothing in terms of information that’s fundamentally new in this movie. So, you know, one, I just, I’m surprised that Hollywood was so resistant to it.
I think it raises a larger question for me and I genuinely don’t have the answer, but I’ve always wondered why it’s considered more controversial to have a scripted version of a story, because we have had plenty of documentaries. I mean, Netflix released a four-part documentary on Trump, I believe, in 2016 or 2017. There have just been numerous documentary treatments of this material. And yet to have actors like Sebastian Stan and Jeremy Strong playing these characters it became this whole other conversation that I didn’t quite understand why is it so much more controversial to have them acting the scenes. Regardless, the end result was that we came out of Cannes without anyone willing to distribute this movie.
Editor’s note: The largest investor in “The Apprentice” was Mark Rapaport, who was given millions of dollars to start his production company Kinematics by his billionaire father-in-law Dan Snyder, one of Trump’s largest political donors. Sherman wrote in Vanity Fair he does not know why the Trump supporter backed the film, “The answer, as best as I can tell, is that Snyder didn’t know what kind of Trump movie his son-in-law was making,” and it was Snyder who was pushing the film be rushed for a Cannes premiere, where he planned to throw a party for the film aboard his 305-foot yacht. But after screening the film for Snyder, Rapaport demanded the sexual assault scene be removed. It was a demand Rapaport contractually couldn’t enforce, but as the largest investor in the film his sign-off was required to accept a distribution deal from Tom Ortenberg’s Briarcliff. When Kinematics refused sign off on the deal, it looked as if the film would not be released prior to the 2024 election.
I understand it’s all speculation as to why a Trump supporter’s money was behind this movie, but I do wonder — and I know we want to be careful with this term — for a moment there when Briarcliff wanted to buy the film and couldn’t, did you feel like this was a case of catch and kill? Did this feel like they were trying to hold up a deal?
I mean, it did feel like that. Again, I’m not ascribing motivations to Kinematics at all, because I genuinely don’t know. But all I do know is that they were not allowing us to sign this distribution deal with Tom Ortenberg’s company, Briarcliff. And we needed to sign this deal basically by Labor Day so that we could get the film ready for release. I mean it is a sprint. We basically signed a deal Labor Day and we’re having the movie released six weeks later. Normally studios spend months on a marketing rollout and we just don’t have that time.
The fact that we couldn’t get our financier to agree meant that if they didn’t sign the deal, the movie would not be released before election and we would not be allowed to release it internationally because of the holdback rights in the contract. So for all intents and purposes, the movie would just not see the light of day, and then it’s unclear what would happen after the election. Perhaps, just do a thought experiment, if Trump wins the election, Hollywood companies were nervous about distributing this film while Trump is just a candidate. Now, put him in the White House. I think the appetite for distributing this movie would go down even more. So from my point of view, it felt like the only window to get this movie released would be before Trump gets in power, if he does win the election.
I never heard a convincing explanation from our financiers as to why, what their plan was if they wouldn’t let us sign the Briarcliff deal, what was their alternative plan to get this movie distributed? I don’t know. And that’s where I started to feel like, well, maybe they don’t want it distributed. The end result is a good friend of mine, Fred Benenson and another investor, James Shani, came together and bought out the Kinematics position, and that freed us up to release the movie.
You said your biggest fear going into “The Apprentice,” was the danger of making a Trump movie that played like a parody. Could you talk about that and how you avoided it?
The danger with trying to dramatize the most famous person in the world is that it would just become an impression. Two things helped to avoid that with this movie. Number one, I always knew that it would be impossible to make a film about present day Trump. There’s just no way to do it because he’s on our TV screens all the time. There’s just no way, no matter how talented an actor is for them to create a character that would feel real when we can see the real life Trump every day. So I knew the only way to make a Trump movie would be to do it about him as a young man. I thought, what if the movie stops when he’s forty years old, and he still looks young and somewhat attractive and he’s not tan the way he is now. That’s such a different version of this character that the audience is going to be able to get lost in the story, they’re not going to be comparing that character to the one we see.
And then secondly, I thought the act that the actor is still going to have to do a version of the character that doesn’t try to mimic Trump. And I think what Sebastian did so brilliantly is that he doesn’t try to impersonate Trump. He finds his own version of the character. And it works in a way where you feel like you’re watching a real person. You’re not watching Sebastian trying to be Donald Trump.
He finds a nice balance. He does things with his mouth that remind you of Trump, and he has certain mannerisms, but it’s not a straight-up impersonation. In terms of doing something with a modern-day Trump, there’s also just something dramatically uninteresting about his current mental state; there’s no change.
No, exactly, that’s exactly right, I’m so glad — that’s a smart observation, because when I was coming up with the idea for the film, I thought that the other thing this movie sets up is the fact that when it ends in the year 1987, the last scene of the film, spoiler alert, at the end of the movie, Trump has become a version of the character that we see today, and I argue that everything that happens after this movie takes place Trump is basically already the same.
He’s like a great white shark that’s just like swimming forward and dramatically that is just a very hard character to write because the essence of drama is change and conflict. So I thought, well, let’s do this movie where the final scene of the movie is, OK, now we see the guy and we don’t need to see anything that comes after it. We don’t even need title cards. The movie ends and you know exactly how Trump became the way he [is] today.
The way it’s written, he was malleable at this stage, and not that Fred Trump (Martin Donovan) was going to rear some great man here, but there is an element of the script saying this intersection with Roy Cohn set a course that wasn’t inevitable that he’d become what he is.
A thousand percent. I recommend to your readers to go watch an interview. It’s, I think, Trump’s first nationally televised interview. It’s on YouTube. If you type in Donald Trump, Rona Barrett, we recreate a version of the scene in the film. I watched this interview in my research and it’s fascinating becausethis interview takes place in 1980 and Trump is soft spoken. He’s articulate. He’s charming. He’s just so different than the man we know today. And it really opened my eyes up to the fact that before he became our version of Trump, he was just a very different person. And so I thought that would be dramatically interesting for that version of Trump to start out one way.
And over the two hours of the movie, we see the evolution of his character. Because you’re right, I argue in this film that it didn’t have to happen this way. I mean, if he hadn’t met Roy Cohn, Donald Trump might have become a loudmouth, New York City real estate developer, but I don’t think he would have had the political toolbox to become the demagogue that he’s become today.
You were convinced an American shouldn’t direct this. Instinctively that makes a lot of sense to me, but I’m curious if you could spell out your logic with this.
I’m a New Yorker. I’ve written about Trump as a journalist for going on 20 years. I’m so close to this material that we thought bringing in an outsider, who’s going to look at it fresh, could have an original point of view that would be really interesting.
Ali’s not afraid of this material. I don’t think he’s afraid of people saying, “Oh, how could you make a movie about Trump?” Cause he’s like, “I’m not American. I’m just going to make a movie that I think captures this world as [I] sees it.” And I always worried an American director would be too political in the sense of like trying to beat the audience over the head with the politics. Ali and I always wanted this to be judged as a film. If you change the names of the characters in your mind and you just sat down and watched this, would this be entertaining as strictly judged as a film? I believe it is. And so I think that’s what freed us up creatively to just try to make this the most compelling version, rather than worrying, “Are we being too hard or too easy on Trump?”
“The Apprentice” opens in theaters on Friday, October 11.
