Vanity Fair – With help from Frank Sinatra and hopes of a postshow burger, the Prada- and Cartier-clad Stan prepared for his first major awards show victory.

Note: Photoshoot and Outtakes (other) are here: Session #155 – Nisha Johny and Jonathan Jacobs

Sebastian Stan entered the Golden Globes 2025 with two chances at winning—nominated for both his portrayal of Donald Trump in The Apprentice and his more comedic performance as Edward, an aspiring actor living with neurofibromatosis, in A Different Man. But in the lead-up to his big night, Stan was eager to put his double nominations into perspective, instead focusing on what he could control: a hearty postceremony meal. “You always read about people having burgers or something after these award shows,” he told Vanity Fair. “I mean, that sounds kind of nice, to be honest.”

A celebratory nosh was well-earned by Stan, who won best actor in a musical-or-comedy film, his first-ever Golden Globe. After thanking A Different Man filmmaker Aaron Schimberg and his costar Adam Pearson, who has the genetic condition neurofibromatosis in real life, Stan advocated for more inclusive narratives onscreen. “Our ignorance and discomfort around disability and disfigurement has to end now,” he said. “We have to normalize it and continue to expose ourselves [and our children] to it. Encourage acceptance.”

A Different Man languished for two years before it debuted at the Sundance Film Festival, and the A24 movie later landed Stan the Silver Bear for best lead performance in Berlin. But The Apprentice, directed by Ali Abbasi and written by Vanity Fair special correspondent Gabriel Sherman, also endured a beleaguered road to distribution in the weeks before the 2024 presidential election. “Both of these films started out as major risks,” Stan told VF shortly before the Globes. As such, he’s not taking any of the recent accolades for granted.

“I feel very blessed that I have good people around me, friends who I’ve had for 20 years at this point, who remember as much as I do what it was like to be in New York City and going out to auditions and not getting it,” said Stan. “Even my mother, who has been with me over the holidays, I was growing up with her in Vienna, Austria, and not even really knowing that I was going to get to America. So when I think about those moments,” he continued, “I’m immediately humbled and on the ground. Because even as it is currently, without anything happening on Sunday, it already feels like such a win.” Stan dedicated the award to his mother and stepfather during his acceptance speech, also taking the time to profess his love to his girlfriend, actor Annabelle Wallis.

Stan spent hours in prosthetics for both A Different Man and The Apprentice, getting comfortable with a bit of metamorphosis. “I kind of liken it, for better or worse, to being in a relationship,” he said of transitioning back to himself postproduction. “I always remember somebody telling me, ‘However long you’ve been with somebody in a relationship, take away half the time, and that’s how long it’s going to take for you to get over them when you break up.’ It’s a little bit like that. It doesn’t just go away suddenly, I guess. There’s a process…that happens with it. It’s sort of a slow, gradual disconnection.”

But does Stan find it harder to disappear into a character or present as himself at an awards show? “That’s a very good question,” he said with a laugh. “Sometimes it’s easier transforming into a role…. Being yourself at an award show, it can be quite tricky, because I’m not going to an award show [thinking], Oh, I’m a funny, interesting guy. I’m feeling self-conscious.”

Nevertheless, Stan was excited to venture beyond his comfort zone in custom Prada. “It’s really fun and different, and it’s something I’ve never really worn before,” he said, crediting stylist Michael Fisher with steering him toward a different era in Hollywood. “You get romantic sometimes when you see clips in black and white of the Oscars and how people dressed up. So I think I’m more old school like that in my mindset rather than, Hey, let me take a crazy swing on this red carpet. Even though, once in a while, Michael has definitely had me in pink.” This time, though, Stan opted for a black mohair coat and trouser with contrasting white piping detail, paired with a black knit wool sweater and white poplin shirt, plus black brushed-leather lace-ups.

Stan’s vintage-Hollywood vision also extended to his pre-Globes playlist. “I don’t mind a little Frank Sinatra,” he told VF. “We’re going to be getting ready at the Hotel Bel-Air, and that hotel itself has such history and that Old Hollywood classic style. I might be playing some ’20s or ’30s music, something that will at least keep me under the illusion that I’m in a different time, because it does feel like a different time.”

As for grooming, Stan said that with age, he’s embraced more facial hair. “I used to be more clean-shaven when I was younger, but it also depends on what I’m working on at the time,” he said. “A lot of how I was looking this year was informed by the fact that I was shooting Thunderbolts, so there was not much I could do. Even with the hair, I don’t always want everything to be perfect or slick. Maybe that just reflects my attitude in terms of staying flexible in the moment with these things—to go, All right, keep it loose and keep it fun.”

Stan never dreamed that A Different Man and The Apprentice would debut in the same year, but they have been in conversation with each other this awards season by virtue of his involvement. “Both films, to me, are about the loss of identity and the loss of self, and to some extent denial of reality and denial of self-acceptance,” said the actor. “Both of the films focus in different ways on characters that go to great lengths to abandon their true selves.”

Stan’s searching, self-conscious characters in the two films meet ego-driven fates. Edward is “obsessed with what he doesn’t have, and then he spends the rest of the film trying to deal with the shame that he’s buried, the shame that he’s never really accepted himself,” said Stan. “Then the Trump story is very obvious to me—it’s a total loss of humanity, empathy and vulnerability, and any morals, sort of at the hands of this very self-indulgent, self-narcissistic way of life. It’s also about how far one can go to deny the truth, deny reality, and lose humanity as a cost.”

Stan’s performance in The Apprentice, which was bested by Adrien Brody’s in The Brutalist for best male actor in a drama film, has faced a particular uphill battle given the utter Trump fatigue in many circles. “Trump is part of our lives. It’s inevitable that we’re talking about him. You go to a coffee shop, and someone’s talking about him; you open your phone, the news, whatever—he’s everywhere, even in the award season,” says Stan, who believes his film will stand the test of time for boldly “challenging, or at least the attempt was to challenge, history as it’s happening rather than waiting.”

With Trump’s second election to the presidency, it feels as if perception of The Apprentice has shifted, as evidenced by its awards season embrace so far. (Stan is also nominated at the upcoming Independent Spirit Awards.) Would that be the case had Trump been defeated? “I don’t know if I know the answer yet to that,” said Stan. “We’re all still trying to figure out how to feel, or to think, about the election and what happened and the next four years.”

In the days before his first Golden Globe victory, which involved a lively backstage reunion with his frequent Marvel costar Anthony Mackie, Stan was similarly open-minded about what’s next. “[In] Eastern Europe, we grow up with a lot of superstitions,” he said. “But this year I just basically surrendered to whatever’s going to happen. Wherever this wild sort of ride I’m on is taking me, I’m just going to kind of follow and really try to be in the moment as much as possible.”