The Most Unexpected Donald Trump Cameos In Film  

Jonathan H. Kantor
124 votes 33 voters 13 items

List Rules Vote up the most surprising Donald Trump cameos.

Donald Trump may be the 45th president of the United States, but the real estate magnate didn't always aspire to become the leader of the free world. For many years, he worked hard to build an acting career. Granted, he was more interested in appearing as himself than he was in playing a character, but the fact remains that Donald Trump has an extensive IMDb profile page.

According to actor Matt Damon, there's a reason Trump was able to show up in so many films, and it's not because of his acting talent. The real estate mogul has a special requirement for Hollywood filmmakers who want to use any of his properties in a film, and Damon explained the clause in an interview with The Hollywood Reporter:

[Director] Martin Brest had to write something in Scent of a Woman - and the whole crew was in on it. You have to waste an hour of your day with a bullsh*t shot: Donald Trump walks in and Al Pacino’s like, “Hello, Mr. Trump!” - you had to call him by name - and then he exits. You waste a little time so that you can get the permit, and then you can cut the scene out. But I guess in Home Alone 2 they left it in.

Because he usually pops up in cameos playing himself or a version of himself, Trump almost always shows up as a surprise. It may seem obvious that the mogul would show up in a movie like Wall Street: Money Never Sleeps, but who expected to see him pop up in Home Alone 2: Lost in New York?

Whether you knew he was coming or not, these movies feature surprising appearances from the future president of the United States. Find the one you think is the most surprising, and vote it up to see which one rises to the top!

Home Alone 2: Lost in New York is listed (or ranked) 1 on the list The Most Unexpected Donald Trump Cameos In Film
Photo:  20th Century Fox

Donald Trump pops up in the second Home Alone film as Kevin McCallister is walking through the Plaza Hotel. The young lad is trying to find the front desk, so he asks a well-dressed gentleman who is walking past. That fellow is, of course, none other than Donald Trump.

Trump had purchased the lush Plaza Hotel just three years before filming began on Home Alone 2 in December 1991. By the time the film hit theaters in November 1992, the Plaza was one of three Trump properties forced into bankruptcy that year.

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Zoolander is listed (or ranked) 2 on the list The Most Unexpected Donald Trump Cameos In Film
Photo:  Paramount Pictures

Donald Trump and his third wife Melania appear in a scene in the movie Zoolander. The couple show up on the red carpet, where Trump gives a short interview about the subject of the film: "Look, without Derek Zoolander, male modeling wouldn’t be what it is today."

Trump's appearance, though brief, is unexpected - seeing as the film is about the world of male modeling. It might have made more sense for the interviewer to grab a soundbite from Melania, who'd been active in the modeling world since the age of 16.

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The Little Rascals is listed (or ranked) 3 on the list The Most Unexpected Donald Trump Cameos In Film
Photo:  Universal Pictures

In a cameo that likely went way over the heads of the film's target demographic, Trump appears as the father of Waldo - the rich, entitled antagonist - in 1994's The Little Rascals.

Trump appears during the film's climactic go-kart race. As the kids are whizzing along, the camera switches to a crowd sitting in some bleachers with Trump centered in the frame. Speaking to Waldo via mobile phone, Trump utters the unforgettable phrase, "You're the best son money can buy."

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The Pickle is listed (or ranked) 4 on the list The Most Unexpected Donald Trump Cameos In Film
Photo:  Columbia Pictures

The Pickle is a comedy from the early 1990s about a filmmaker trying to revitalize his career after a series of flops. In a case of life imitating art, The Pickle flopped with both audiences and critics. The movie's failure probably wasn't due to its brief cameo from Donald Trump.

In the film, Trump can be seen standing across the street from the Plaza Hotel as the crew is setting up their equipment. The mogul then turns to a random person and asks, "Who gave them permission to shoot in front of the Plaza?" Of course, Trump is the only person who could have given that permission.

Ironically, by the time The Pickle hit theaters in '93, Trump had given up his controlling percentage, salary, and day-to-day role in the operations of the Plaza

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