Before entering politics, Donald Trump was already a familiar face in pop culture. Known worldwide as a New York real-estate mogul, Trump made several brief but memorable appearances in popular movies and television shows — often playing himself or a wealthy businessman.
Some of these cameos became iconic, while others slipped past audiences unnoticed. Here are five Donald Trump appearances in movies and TV that many viewers completely missed.
1. Home Alone 2: Lost in New York (1992)
This is undoubtedly Trump’s most famous cameo. When young Kevin McCallister (Macaulay Culkin) finds himself stranded at the Plaza Hotel, he stops a tall man in a long coat to ask for directions.
- The Scene: Kevin asks, “Excuse me, where’s the lobby?” Trump responds, “Down the hall and to the left.”
- Fun Fact: Trump actually owned the Plaza Hotel at the time! Director Chris Columbus recently revealed that Trump only allowed filming in the hotel if he was given a part in the movie.
2. The Little Rascals (1994)
In this classic family comedy, Trump took on a rare fictional role rather than playing himself. He played the wealthy father of the “rich kid” antagonist, Waldo.
- The Scene: During the big race at the end of the film, Trump is seen on a cellular phone (a huge one, typical of the 90s!) telling his son, “You’re the best son money can buy.” It was the perfect tongue-in-cheek nod to his billionaire persona.
The cameo became one of the film’s most quoted jokes.
3. Zoolander (2001)
In this cult-classic satire of the fashion industry, Trump appears alongside his wife, Melania Trump, during a fictional red-carpet interview.
- The Scene: He praises the legendary male model Derek Zoolander (Ben Stiller), stating that without Derek, male modeling wouldn’t be what it is today.4.
The moment fits perfectly with the film’s exaggerated humor and celebrity cameos.
4. Sex and the City (1999)
Trump was the ultimate symbol of New York City luxury, so it’s no surprise he appeared in Sex and the City.
- The Scene: In the episode “The Man, the Myth, the Viagra,” he is seen having a business meeting in a restaurant. As Samantha Jones spots him, Carrie’s iconic voiceover remarks, “Donald Trump… you just don’t get more New York than that.”
5. Two Weeks Notice (2002)
In this rom-com starring Hugh Grant and Sandra Bullock, Trump makes a brief but memorable appearance at a high-society cocktail party.
- The Scene: He has a brief, awkward exchange with Hugh Grant’s character, George Wade, showcasing his real-life “business mogul” vibe that fans of The Apprentice would soon come to love.
Final Thoughts
Donald Trump’s movie and TV cameos weren’t about acting — they were about presence. Whether giving directions in a hotel lobby or appearing on a red carpet, these moments captured a specific era of pop culture when Trump symbolized New York luxury and high-profile business success.
Long before reality television and politics, Hollywood had already made him a familiar face.
