Why Sebastian Stan's Donald Trump Role Left Him With 'Sleepless Nights'

Sebastian Stan, best known for his role as Bucky Barnes/Winter Soldier in the Marvel Cinematic Universe, recently stepped into one of his most challenging roles yet: portraying a young Donald Trump in the film “The Apprentice,” written by Gabriel Sherman and directed by Ali Abbasi.

The film dives into Trump’s rise as a real estate mogul in 1970s and 1980s New York City, exploring the ambition, power struggles, and personal controversies that shaped his early career.

Sebastian Stan’s portrayal offers a closer look at Donald Trump’s formative years, capturing the complexities of the man who would later become one of the most polarizing figures in modern political history.

Sebastian Stan Claims His Donald Trump Role Was His Most Challenging

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At the 2025 Golden Globe Awards, where Stan accepted the trophy for Best Performance by a Leading Actor in a Musical or Comedy Film for his role in “A Different Man,” he was asked about his most challenging role to date.

Without hesitation, he pointed to “The Apprentice.”

“Without a doubt, the man in orange, right? Donald Trump, definitely the hardest,” Stan said, per People, with a wry smile before acknowledging the challenges of his Golden Globe-winning role. “And that is not to diminish why I’m up here right now talking to you. I think this in itself is really difficult. There was a big risk in terms of what it speaks to and trying to walk into somebody else’s shoes who has more -osis, like Adam Pearson. So that had its own challenges as well, and I wanted to do that right.”

Stan continued, reflecting on the weight of playing such a controversial figure. “But in terms of when I look back at the sleepless nights and the responsibility that I feel I carried—and still feel—it’s about ‘The Apprentice’ and wanting to do the best that I can to honor the boss division and to offer further perspective on something that I think we’re all inevitably having to do.”

‘The Apprentice’ Gains Mixed Reviews

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When the film first premiered at the Cannes Film Festival in May 2024, it was met with both praise and controversy -- and those reviews continued after its official release in October 2024. Its unflinching portrayal of Trump’s personal and professional life includes a deeply unsettling scene involving Trump, played by Stan, and his first wife, Ivana, portrayed by Maria Bakalova.

One of the scenes draws from Ivana Trump’s 1990 divorce deposition, where she described a distressing encounter with her then-husband. “On one occasion during 1989, Mr. Trump and I had marital relations in which he behaved very differently towards me than he had during our marriage,” Ivana said, as reported by The Guardian. “As a woman, I felt violated … I referred to this as a rape, but I do not want my words to be interpreted in a literal or criminal sense.”

Legal Drama Surrounds ‘The Apprentice’

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After the May premiere, Steven Cheung, communications director for the Trump campaign, issued a statement to People, claiming, “We will be filing a lawsuit to address the blatantly false assertions from these pretend filmmakers.”

“This garbage is pure fiction which sensationalizes lies that have been long debunked,” Cheung added, referring to the rape scene. “This ‘film’ is pure malicious defamation, should not see the light of day, and doesn’t even deserve a place in the straight-to-DVD section of a bargain bin at a soon-to-be-closed discount movie store. It belongs in a dumpster fire.”

Sebastian Stan Gets Candid

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During a November 2024 screening in Los Angeles, Sebastian Stan revealed that he was invited to participate in Variety’s renowned Actors on Actors series but ultimately couldn’t take part due to difficulties in finding a suitable pairing. The candid admission, reported by Buzzfeed, sheds light on the challenges actors can face when tackling projects with complex or sensitive subject matter.

“They were too afraid to go and talk about this movie, so I couldn’t do it,” Stan shared at the November 19 event. “And it doesn’t matter, that’s OK. It’s not to point a finger at anybody — I’ve got to do a lot of great things.”

Stan clarified that no single individual was to blame for the missed opportunity. Instead, he suggested that representatives and publicists may have been hesitant to engage in discussions about the film’s themes. “We couldn’t get past the publicists or the people representing them because they were too afraid to talk about this movie,” he explained.

Sebastian Stan Wins Golden Globe For His Role In ‘A Different Man’

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The acclaimed actor was nominated twice at Sunday’s ceremony: once for his role in “The Apprentice” and once for “A Different Man,” winning the latter over notable contenders such as Jesse Eisenberg, Gabriel LaBelle, Hugh Grant, Jesse Plemons, and Glen Powell.

In his acceptance speech, Stan addressed the profound impact of “A Different Man” and the societal attitudes it confronts. Calling it “not an easy” movie to make, he emphasized the need for greater understanding and representation.

“Our ignorance and discomfort around disability and disfigurement has to end now,” Stan said passionately. “We have to normalize it and continue to expose ourselves to it and encourage acceptance in our children. One way we can do that is by continuing to champion stories that are inclusive.”

Both “The Apprentice” and “A Different Man” are now available to rent or buy on-demand, allowing audiences to experience the powerful performances and important narratives Stan has brought to life on screen.