SeeThe ApprenticeCast Side-by-Side with the Real-Life People They Play (Including Sebastian Stan as a Young Donald Trump)

Mar. 15, 2025

Sebastian Stan filming The Apprentice, Donald Trump.Photo:TheImageDirect.com; Universal History Archive/Universal Images Group via Getty

TheImageDirect.com; Universal History Archive/Universal Images Group via Getty

Long before businessman and former PresidentDonald Trumpwas firing contestants on his NBC reality show,The Apprentice, he was an apprentice himself.

In 1973, a young Trump met Roy Cohn — a cutthroat (and controversial) New York City attorney known for having friends in very high places. In the decade that followed, Cohn served as Trump’s mentor until the lawyer’s death in 1986.

“But it’s also a story of a system, the depiction of the American system, the legal system, the inherent corruption in a system that allowed people like Roy Cohn to navigate freely and sort of pull the levers of power as they see fit," Abbasi toldThe Wrapof the project, which will premiere in 2,000 select theaters on Oct. 11.

“It’s an entertaining character piece.It’s not a hit piece," he added.

“It was a24/7 immersion processof living with him to some extent in my headphones,” Stan said of transforming into Trump for the film. “Whatever I was doing, if I was in the bathroom, I was listening to him. I don’t know how else to do it, except 100%.”

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Sebastian Stan as Donald Trump

Sebastian Stan filming The Apprentice, Donald Trump.TheImageDirect.com; Joe McNally/Getty

TheImageDirect.com; Joe McNally/Getty

“I think, my wanting to do this movie, and why I respect [Abbasi] for having the balls to do it, is because it does attack that very discomfort that you are referencing towards this film,” he explained toThe Hollywood Reporterin September 2024.

“Everything in this film happened,” he added. “People perhaps like to forget that [Trump] was onOprahandDavid LettermanandLarry King, and everybody embraced him and was championing him to be who he was in the eighties.”

02of 08Jeremy Strong as Roy CohnJeremy Strong and Roy Cohn.Briarcliff Entertainment/YouTube; Betty Galella/Ron Galella Collection/GettyJeremy Strong plays attorney Roy Cohn, who is best known for serving as Senator Joseph McCarthy’s chief counsel during the Army–McCarthy hearings in 1954 and the man who helped Trump rise to power in the business world. Cohn died of complications from AIDS in 1986 at the age of 59.“Roy Cohn, you can’t overstate his influence in our country, his legacy of the denial of reality and certain things that he imparted to Donald Trump,” Strong said during an interview withThe New York Times Magazinein March 2024.“His playbook has a tentacular reach that is staggering — the most fascinating person I’ve ever tried to inhabit," he continued. “I should say a disclaimer: My job is to be a humanistic investigator of a subject and to withhold judgment. So while I personally might have a lot of judgment about Roy Cohn, that is not the part of me that engages in the creative work.”

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Jeremy Strong as Roy Cohn

Jeremy Strong and Roy Cohn.Briarcliff Entertainment/YouTube; Betty Galella/Ron Galella Collection/Getty

Briarcliff Entertainment/YouTube; Betty Galella/Ron Galella Collection/Getty

Jeremy Strong plays attorney Roy Cohn, who is best known for serving as Senator Joseph McCarthy’s chief counsel during the Army–McCarthy hearings in 1954 and the man who helped Trump rise to power in the business world. Cohn died of complications from AIDS in 1986 at the age of 59.

“Roy Cohn, you can’t overstate his influence in our country, his legacy of the denial of reality and certain things that he imparted to Donald Trump,” Strong said during an interview withThe New York Times Magazinein March 2024.

“His playbook has a tentacular reach that is staggering — the most fascinating person I’ve ever tried to inhabit,” he continued. “I should say a disclaimer: My job is to be a humanistic investigator of a subject and to withhold judgment. So while I personally might have a lot of judgment about Roy Cohn, that is not the part of me that engages in the creative work.”

03of 08Maria Bakalova as Ivana TrumpMaria Bakalova and Ivana Trump.Briarcliff Entertainment/YouTube; Ron Galella/Ron Galella Collection/GettyMaria Bakalova portrays Trump’s first wife,Ivana Trump. The pair were married from 1977 to 1990 and had three children:Donald Trump Jr.,Ivanka TrumpandEric Trump. Ivana died in 2022 at the age of 73.“I hope I play her with respect and dignity because learning about her made me inspired,” Bakalova toldDeadlinein May 2024, calling Ivana a “boss lady” and a “dedicated mother.“The actress added: “She wanted to live life. She loved to dance, loved to eat, loved to have experiences. We have this privilege to enjoy every single minute [of life]. And she was all about that.”

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Maria Bakalova as Ivana Trump

Maria Bakalova and Ivana Trump.Briarcliff Entertainment/YouTube; Ron Galella/Ron Galella Collection/Getty

Briarcliff Entertainment/YouTube; Ron Galella/Ron Galella Collection/Getty

Maria Bakalova portrays Trump’s first wife,Ivana Trump. The pair were married from 1977 to 1990 and had three children:Donald Trump Jr.,Ivanka TrumpandEric Trump. Ivana died in 2022 at the age of 73.

“I hope I play her with respect and dignity because learning about her made me inspired,” Bakalova toldDeadlinein May 2024, calling Ivana a “boss lady” and a “dedicated mother.”

The actress added: “She wanted to live life. She loved to dance, loved to eat, loved to have experiences. We have this privilege to enjoy every single minute [of life]. And she was all about that.”

04of 08Martin Donovan as Fred Trump Sr.Martin Donovan and Fred Trump.Pascal Le Segretain/Getty; Rita Barros/GettyMartin Donovan playsFred Trump Sr., Trump’s father.In 1927, Fred launched his real estate career — an empire his youngest son would eventually inherit. He got his start building single-family homes in New York City’s Queens before going on to develop luxury apartment buildings and hotels, such as Trump Tower in Manhattan. Fred died in 1999 at age 93.

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Martin Donovan as Fred Trump Sr.

Martin Donovan and Fred Trump.Pascal Le Segretain/Getty; Rita Barros/Getty

Pascal Le Segretain/Getty; Rita Barros/Getty

Martin Donovan playsFred Trump Sr., Trump’s father.

In 1927, Fred launched his real estate career — an empire his youngest son would eventually inherit. He got his start building single-family homes in New York City’s Queens before going on to develop luxury apartment buildings and hotels, such as Trump Tower in Manhattan. Fred died in 1999 at age 93.

05of 08Joe Pingue as Anthony SalernoJoe Pingue September 17, 2019 and Anthony Salerno 1986.Paul Archuleta/Getty; Bureau of Prisons/GettyJoe Pingue portrays American mobster Anthony “Fat Tony” Salerno inThe Apprentice.Cohn served as Salerno’s lawyer for many years. Salerno died at age 80 in 1992.

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Joe Pingue as Anthony Salerno

Joe Pingue September 17, 2019 and Anthony Salerno 1986.Paul Archuleta/Getty; Bureau of Prisons/Getty

Paul Archuleta/Getty; Bureau of Prisons/Getty

Joe Pingue portrays American mobster Anthony “Fat Tony” Salerno inThe Apprentice.

Cohn served as Salerno’s lawyer for many years. Salerno died at age 80 in 1992.

06of 08Charlie Carrick as Fred Trump Jr.Charlie Carrick September 11, 2022 and Fred Trump III.Matt Winkelmeyer/Getty; Andrew Savulich/GettyCharlie Carrick plays Fred Trump Jr. — Donald Trump’s older brother.Fred was a pilot, much to his dad’s chagrin, and struggled with alcoholism. In 1981, he died of a heart attack at age 42.

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Charlie Carrick as Fred Trump Jr.

Charlie Carrick September 11, 2022 and Fred Trump III.Matt Winkelmeyer/Getty; Andrew Savulich/Getty

Matt Winkelmeyer/Getty; Andrew Savulich/Getty

Charlie Carrick plays Fred Trump Jr. — Donald Trump’s older brother.

Fred was a pilot, much to his dad’s chagrin, and struggled with alcoholism. In 1981, he died of a heart attack at age 42.

07of 08Mark Rendall as Roger StoneMark Rendall at the Tribeca Film Festival red carpet arrivals for the film “Stockholm” in New York City 2018; Roger Stone attends Roger Stone Exclusive Photo Session on August 19, 1987 at Alan Flusser Boutique in New York City.Michael Brochstein/Getty; Ron Galella/Ron Galella Collection/GettyMark Rendall portrays Roger Stone — a longtime friend and political advisor to Trump. Stone first met Trump and Cohn over bagels when he was trying to raise money for Ronald Reagan’s presidential campaign in 1980.In November 2019, Stone was convicted of seven charges — including lying to Congress under oath, obstruction of a congressional investigation and tampering with a witness duringthe Trump-Russia investigation. However, then-President Trump commuted his sentence in July 2020.

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Mark Rendall as Roger Stone

Mark Rendall at the Tribeca Film Festival red carpet arrivals for the film “Stockholm” in New York City 2018; Roger Stone attends Roger Stone Exclusive Photo Session on August 19, 1987 at Alan Flusser Boutique in New York City.Michael Brochstein/Getty; Ron Galella/Ron Galella Collection/Getty

Michael Brochstein/Getty; Ron Galella/Ron Galella Collection/Getty

Mark Rendall portrays Roger Stone — a longtime friend and political advisor to Trump. Stone first met Trump and Cohn over bagels when he was trying to raise money for Ronald Reagan’s presidential campaign in 1980.

In November 2019, Stone was convicted of seven charges — including lying to Congress under oath, obstruction of a congressional investigation and tampering with a witness duringthe Trump-Russia investigation. However, then-President Trump commuted his sentence in July 2020.

08of 08Ben Sullivan as Russell EldridgeBen Sullivan attends the premiere of Roadside Attractions' ‘Stonewall’ at the Pacific Design Center on September 23, 2015 in West Hollywood, California.Barry King/GettyBen Sullivan playsRussell Eldridge— Cohn’s private secretary. He died of AIDS in 1985.

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Ben Sullivan as Russell Eldridge

Ben Sullivan attends the premiere of Roadside Attractions' ‘Stonewall’ at the Pacific Design Center on September 23, 2015 in West Hollywood, California.Barry King/Getty

Barry King/Getty

Ben Sullivan playsRussell Eldridge— Cohn’s private secretary. He died of AIDS in 1985.

source: people.com