It’s hard to believe that there was a time Donald Trump wasn’t in the news every single day, and instead would just spend his time popping in and out of films and TV shows in glorifying cameos whenever he felt like it.
The former US President is currently gearing up for the upcoming election, facing off against Democratic candidate Kamala Harris in the polls next week.
Ahead of the 2024 US Presidential Election, which has been described as a ‘long, brutal, drawn-out, miserable slog’, we looked back over the 78-year-old’s efforts in Hollywood, including ‘bullying’ his way into his infamous stint in Home Alone 2, and a brief moment in Sex and the City.
It’s fair to say those moments now remind viewers of a much simpler time, when misinformation wasn’t as rampant and the Republican candidate wasn’t spewing shade at some of the biggest stars in the world.
Here are some of Trump’s most bizarre, scene-stealing moments from the 1990s and early 2000s…
One of Trump’s first – and most recognized – big screen moments came in 1992 when he happened to be strolling around the Plaza at just the right time in Home Alone 2: Lost in New York.
It is common knowledge that if you filmed in a property owned by the businessman at the time, you had to give him a role in the project.
With much of the Christmas classic being filmed at the Plaza Hotel, he requested a starring role that is still in the final cut today.
In a blink-and-you’ll-miss-it moment, Macaulay Culkin’s Kevin McCallister approached him to ask where the lobby was, and he uttered the now-infamous phrase: ‘Down the hall and to the left’.
Cinematographer Julio Macat lifted the lid on the festive flick in a chat with in 2020, shedding light on what it was like briefly working with the politician.
‘We shot at the Plaza Hotel, which at the time was run by Trump,’ he told us. ‘He was such a ham.
‘He would be around the filming, we filmed in the hotel, we stayed there for almost a month and a half, at the Plaza.
‘We filmed in their lobby and he was around, and he had to be in the movie, he had to photobomb the shoot one day, and came walking in with his entourage, and wanted to walk through the shot.
‘Of course, we said yes because we’re filming in his hotel. As he does the shot, he turns the looks to the camera, so you could really see his face.’
Director Chris Columbus later opened up about that scene in an interview with Insider, claiming that Trump ‘bullied’ his way in front of the camera.
‘We approached The Plaza Hotel, which Trump owned at the time, because we wanted to shoot in the lobby. We couldn’t rebuild The Plaza on a soundstage,’ he recalled. ‘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.”
‘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.’
Trump hit back at his comments last year, alleging that those behind the screen actually begged him to make an appearance, while also crediting himself with the huge success of the movie.
‘They rented the Plaza Hotel in New York, which I owned at the time,’ he said on Truth Social. ‘I was very busy, and didn’t want to do it. 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. People call me whenever it is aired.
‘Now, however, 30 years later, Columbus (what was his real name?) put out a statement that I bullied myself into the movie.
‘Nothing could be further from the truth.’
Trump followed this up with yet another cameo but swapped New York for California to appear in the Fresh Prince of Bel-Air, sharing the screen with Will Smith, Alfonso Ribeiro, James Avery, Tatyana Ali and co.
In the season four episode, For Sale By The Owner – which first aired in May, 1994 – he strolled into the Banks’ Bel-Air household, ready to open up his wallet and purchase the property.
It was down to Geoffrey to announce his presence, after which Carlton cheered, It’s the Donald! Oh my God,’ before fainting.
‘I like keeping a low profile,’ Trump told his hosts as Hilary flirted: ‘You look much richer in person.’
While the rest of the family rushed to impress their guest, Ashley thanked him for ‘ruining her life’, to which he uttered a now cryptic premonition: ‘Everybody’s always blaming me for everything…’
Although ‘the Donald’ didn’t end up buying their property, that wasn’t the end of his ‘rich guy’ screen persona.
Months after his trip to Bel-Air, Trump enjoyed a very quick appearance in the Little Rascals reboot, in one of his only character roles – playing the dad of an obnoxious rich kid named Waldo.
As the youngster (Blake McIver Ewing) picked up a humungous phone to call his parents, the former President was on the other end.
‘Hi dad, it’s me,’ he said. ‘You’re going to be so proud of me. I’m going to win this race!’
Trump, credited simply as ‘Waldo’s dad’, replied: ‘Waldo, you’re the best son money can buy.’
The Apprentice host soon got back to playing himself during a stint in Sex and the City, making a cameo in the season two episode, the Man, the Myth, the Viagra.
During the instalment, which hit the small screen in 1999, Samantha Jones (Kim Cattrall) was filmed sitting at a bar while the camera panned to the man she was trying to date at the time, who happened to be sat across from the businessman.
In a voiceover, Carrie (Sarah Jessica Parker) said: ‘Samantha, a cosmopolitan, and Donald Trump… You just don’t get more New York than that.’
‘Listen man, I’ve got to go,’ he told Samantha’s beau. ‘But think about it. I’ll be at my office at Trump Tower.’
Detailing the episode in Jennifer Keishin Armstrong’s book, Sex and the City and Us, the writers later vowed that they would scrap his appearance if they made the show again.
‘If we could do it over again the main thing we would choose is not to involve Donald Trump,’ they declared, according to the New York Daily News.
Ben Stiller didn’t feel quite the same way as the SATC writers while reflecting on Trump’s brief screen moment in 2001’s Zoolander, alongside Melania Trump.
During a fictional red carpet interview, the Republican heaped praise on his titular character, raving: ‘Without Derek Zoolander, male modeling wouldn’t be what it is today.’
Unpacking the scene on the New Abnormal podcast in 2020, Stiller said: ‘We were shooting at the now defunct VH1 Fashion Awards.
‘As people were coming up the red carpet, we pulled them aside and asked them to talk about Derek Zoolander, and so Trump and Melania did that.
‘I’ve had people reach out to me and say, “You should edit Donald Trump out of Zoolander”. But at the end of the day, that was a time when that exists and that happened.
‘There were so many movies that had a silly cameo from Donald Trump. He represented a certain thing.’
Two Weeks Notice – 2002
Trump had another starring role in the early 00s, this time opposite Sandra Bullock and Hugh Grant in 2002 rom-com, Two Weeks Notice.
He was able to utter seven words to Grant’s character, George Wade, telling him: ‘Wait, I hear [Lucy] Kelson finally dumped you!’
However, he didn’t quite leave a lasting impression on Grant, who admitted that the former President ‘didn’t really register’ because he had more important things to think about.
Appearing on the Graham Norton Show earlier this month, he said: ‘He played a bit part as himself in a romantic comedy I did with Sandra Bullock. But the fact is that I don’t really remember him very well.
‘The night he came, I had a bet with Sandy that I could make the chairman of Warner Brothers cry by 9pm. I was completely focused on that.
‘It was quite a big bet. She didn’t believe I could do it, but I did it.’
‘I’m afraid Donald Trump didn’t really register,’ Grant insisted. ‘All I remember is that, a day or two afterwards, I got a call to say, “You’ve been made a member of Trump National New York – which was a golf club.
‘I don’t remember him greatly as a person.’
Ouch…