Before scoring the presidency, Donald Trump managed to negotiate numerous cameo appearances on the big screen.
Throughout the ’90s and early ’00s, it wasn’t unusual for the former Apprentice star to pop up alongside A-list Hollywood actors like Macaulay Culkin and Hugh Grant.
Trump’s foray into the movies was savvy. He used these bit roles to strengthen his image and reputation as a powerful and recognizable New York businessman, and to some extent it worked.
According to claims, when directors came knocking to ask for permission to shoot at his properties, he allegedly would only agree if they would put him in it.
Trump, however, has previously claimed he was begged by filmmakers to make cameos.
Here, Daily Mail takes a closer look at Trump’s film cameos.
Trump, now 79, made his first on-screen acting appearance in the 1989 box office flop, Ghosts Can’t Do It.
The romcom, which starred Bo Derek and Anthony Quinn, was panned by critics and won Worst Picture, Worst Actress and Worst Actress at the 11th Golden Raspberry Awards.
President Donald Trump made numerous film appearances before assuming office
The businessman made his film debut in the 1989 box office flop Ghosts Can’t Do It
Of the president’s performance, San Francisco Chronicle journalist Mick LaSalle observed that he ‘squints and makes fish lips after every line of dialogue. Interesting choice.’
Trump’s arguably most famous film cameo came three years later when he appeared as himself in the 1992 sequel Home Alone 2: Lost in New York.
The famous scene saw Kevin McCallister – played by Macaulay Culkin – ask Trump to point him in the direction of the Plaza Hotel, which the president owned at the time.
In December 2020, the film’s director Christopher Columbus said in an interview that Trump had made his cameo part of the deal in order for production to use the Plaza, which Trump owned at the time.
He explained to Business Insider at the time that they needed to shoot at the Plaza because it was something that couldn’t be reconstructed on a soundstage.
Columbus said that like most locations in New York, ‘you just pay a fee and you are allowed to shot in that location.’
But when production approached the Plaza, the deal came with an extra ask.
‘Trump said okay. We paid the fee, but he also said, “The only way you can use the Plaza is if I’m in the movie.”
Trump famously appeared in the Home Alone sequel alongside Macaulay Culkin in 1992
While he typically appeared as himself, Trump played Waldo Johnston II in The Little Rascals
‘So we agreed to put him in the movie, and when we screened it for the first time the oddest thing happened: People cheered when Trump showed up on-screen.
‘So I said to my editor, “Leave him in the movie. It’s a moment for the audience.” But he did bully his way into the movie,’ Columbus shared.
Trump blasted Columbus’s claims, however, and insisted in December 2023 that the director had ‘begged him’ to make the cameo.
‘I was very busy, and didn’t want to do it,’ he claimed on Truth Social. ‘They were very nice, but above all, persistent. I agreed, and the rest is history!’
‘That little cameo took off like a rocket, and the movie was a big success, and still is, especially around Christmas time,’ he added. ‘People call me whenever it is aired.’
In 1994, Trump starred as Waldo Johnston II in The Little Rascals, one of his only character roles.
His character was father of an obnoxious rich kid named Waldo, played by Blake McIver Ewing.
In his scene, young Waldo phoned his father to present him with some good news.
‘Hi dad, it’s me,’ he said. ‘You’re going to be so proud of me. I’m going to win this race!’
Trump replied: ‘Waldo, you’re the best son money can buy.’
Trump and his wife Melania popped up in the 2001 comedy film Zoolander
In 2002, he appeared in the romcom Two Weeks Notice in a scene with Hugh Grant
According to the film’s director Penelope Spheeris, Trump ‘fit perfectly as the father of the spoiled brat who had no connection to the rest of the world.’
Trump made further cameos in Across the Sea of Time in 1995 and Eddie and The Associate, released in 1996.
In 1998, he played a VIP Patron in Mark Christopher’s drama 54, which starred Ryan Phillippe, Salma Hayek, Neve Campbell and Mike Myers.
The cameos continued into the millennium and in 2001, Trump had a small part in Zoolander alongside Ben Stiller.
In the comedy, Trump and now-wife Melania were in a scene in which they were interviewed on the red carpet of the VH1 Fashion Awards in New York City.
The future president said in the film: ‘Without Derek Zoolander male modeling wouldn’t be what it is today.’
Ben Stiller defended casting Trump in Zoolander by saying ‘there were so many movies that had a silly cameo from him’
Director Oliver Stone said Trumps acting ‘wasn’t bad’ despite cutting his scene from Wall Street: Money Never Sleeps
Stiller, who directed, produced and played the titular role of Derek Zoolander in the motion picture, said that he was keeping the film intact, as it was reflective of what was going on at the time.
‘There were so many movies that had a silly cameo from Donald Trump,’ he said. ‘He represented a certain thing.’
Trump at the time was a New York City staple and three years from doing The Apprentice on NBC.
One year later, he popped up in Two Weeks Notice, Marc Lawrence’s romantic comedy which starred Sandra Bullock and Hugh Grant.
In the film, he uttered to Grant’s character George Wade: ‘Wait, I hear [Lucy] Kelson finally dumped you!’
Trump’s last cameo came in 2010 when he appeared in Oliver Stone’s drama Wall Street: Money Never Sleeps – but the scene didn’t make it to the final cut.
The president was set to play himself in the sequel, which starred Michael Douglas as the now reformed cutthroat investment banker Gordon Gekko.
Stone insisted that Trump’s acting abilities weren’t to blame for his scene ending up on the cutting room floor.
‘He’s in the deleted scene — not because it was bad but just because it was too long — but I worked with him for about a day with Michael Douglas,’ he said in 2016. ‘He wasn’t bad.’
