Trump's Cameo Moments in Film: How the 47th President Made His Mark on Hollywood

All the Movies Donald Trump Was In: From Home Alone 2 to His Return as 47th President

Okay, let’s be real—Donald Trump might not be the first name you think of when it comes to Hollywood star power. But if you dig into the archives, you’ll find that Trump has actually popped up in a bunch of iconic movies. Yup, the guy who recently secured a return to the White House as the 47th president had his fair share of Hollywood cameos, and they’re every bit as over-the-top as you’d imagine. From helping Kevin find the lobby in Home Alone 2 to appearing as a party-goer in Zoolander, Trump’s roles all share one thing: they’re about glitz, glamour, and his signature “Trump” vibe. So, whether you remember these scenes or are hearing about them for the first time, let’s take a stroll through Trump’s unexpected film career. Get ready for some major throwbacks and laughs—you might just find yourself surprised by where he shows up!

Movies Appearances

1. Home Alone 2: Lost in New York (1992)

Scene: Around 25 minutes into the movie, Trump appears as Kevin McCallister (Macaulay Culkin) roams the Plaza Hotel. Kevin, lost and trying to find the lobby, asks Trump for directions. Trump gives a quick answer, guiding him toward the lobby, creating one of the most iconic moments in the film.

Fun Fact: Trump owned the Plaza Hotel at the time, and reportedly, his cameo was part of the deal for allowing the film to shoot there.

2. The Little Rascals (1994)

Scene: About 45 minutes into the movie, Trump appears briefly as the father of Waldo, the spoiled rich kid in the “He-Man Woman Haters Club.” During a phone call, Trump scolds Waldo, saying, “Waldo, you're the best son money can buy," adding a comedic touch.

Fun Fact: Trump’s line reflects his “money can buy anything” persona, giving a wink to his public image at the time.

3. Zoolander (2001)

Scene: Roughly 7 minutes into Zoolander, Trump appears as himself, praising male model Derek Zoolander at an award ceremony, saying, “Without Derek Zoolander, male modeling wouldn’t be what it is today.” His quick line adds to the celebrity-studded atmosphere.

Fun Fact: Trump’s cameo alongside other celebrities, like his then-wife Melania Trump, helped elevate the movie’s satirical take on the fashion industry.

4. Celebrity (1998)

Scene: In Woody Allen's film Celebrity, Trump appears about 25 minutes in, playing himself. He shares the screen with actor Charlize Theron, appearing at a posh Manhattan party. He talks briefly about his public image, a subtle nod to his persona in New York high society.

Fun Fact: Trump’s presence reflects the theme of fame and the obsession with celebrity culture, fitting right into Allen’s satirical storyline.

5. Two Weeks Notice (2002)

Scene: About 12 minutes into the film, Trump makes a cameo as himself, greeting Sandra Bullock’s character, Lucy, at a social event. Trump playfully acknowledges her boss, played by Hugh Grant, with a lighthearted exchange.

Fun Fact: The cameo in Two Weeks Notice captures Trump’s connection to New York City’s elite circles, which is central to the film’s backdrop.

6.Eddie (1996)

Scene: Around 53 minutes in, Trump appears courtside at a New York Knicks game as Whoopi Goldberg’s character, Eddie, becomes the team’s new coach. He briefly praises Eddie’s unusual coaching style, adding some star power to the sports comedy.

Fun Fact: Trump was often seen at real Knicks games, making this cameo a perfect reflection of his real-life interests in sports and entertainment.

7. 54 (1998)

Scene: About 20 minutes into this film, which is set at the iconic Studio 54 nightclub, Trump appears in a quick shot mingling with guests. He’s seen in a party setting, fitting with the film’s focus on celebrity culture in the 1970s.

Fun Fact: Given his ties to New York’s nightlife scene, Trump’s appearance at Studio 54 was a nod to his status in the city’s social elite.

8. Wall Street: Money Never Sleeps (2010)

Scene: Near the beginning of the film, around 6 minutes in, Trump makes a quick cameo as a Wall Street insider. His appearance as a symbol of wealth fits perfectly into the world of finance and high stakes portrayed in the movie.

Fun Fact: Trump’s cameo taps into his well-known image as a real estate mogul and business magnate, blending seamlessly with the movie’s themes.

9. Ghosts Can't Do It (1989)

Scene: Trump plays himself in a small role where he interacts with the main character, played by Bo Derek. In the film, Trump appears as a ruthless businessman, even delivering a line about power, which fits his public image.

Fun Fact: Trump actually won a “Worst Supporting Actor” Razzie Award for this role, a testament to the film's infamy and his over-the-top portrayal.

10. The Associate (1996)

Scene: About halfway through this Whoopi Goldberg comedy, Trump briefly appears as himself, greeting Goldberg’s character as she rises in the male-dominated world of finance. Trump’s cameo nods to his fame in New York’s business scene.

Fun Fact: This cameo reinforced Trump’s reputation as a staple in New York’s elite business and social circles.

11. Marmalade (2004)

Scene: In this indie film, Trump has a quick, blink-and-you’ll-miss-it appearance. He’s seen as part of a flashy New York scene, emphasizing his “always in the spotlight” image.

Fun Fact: Marmalade is lesser-known, but Trump’s inclusion, even briefly, kept him connected to New York’s film culture.

TV Show Appearances

1. The Fresh Prince of Bel-Air (1994)

Scene: In the episode “For Sale By Owner,” Trump makes a cameo alongside his then-wife Marla Maples when they visit the Banks’ mansion, considering buying the property. Trump’s appearance plays into his reputation as a wealthy mogul, much to the amazement of Will and the rest of the family.

Fun Fact: Trump’s cameo was a ratings hit and added to his “rich real estate guy” image, which The Fresh Prince audience found hilarious.

2. The Nanny (1996)

Scene: In the episode “The Rosie Show,” Trump appears briefly as himself, attending a fictional talk show. Fran Fine (played by Fran Drescher) is delighted to spot him in the audience and makes a big deal about his appearance.

Fun Fact: Fran Drescher later recalled that Trump was one of the most memorable guest stars on The Nanny, adding to the show’s roster of high-profile guest appearances.

3. Sex and the City (1999)

Scene: Trump appears as himself in the episode “The Man, The Myth, The Viagra,” where Samantha and her friends spot him in a Manhattan restaurant, cementing his status as a fixture in New York’s elite social scene.

Fun Fact: Trump’s cameo was brief, but his presence in Sex and the City helped showcase him as an icon of NYC’s nightlife.

4. Spin City (1998)

Scene: Trump makes a quick appearance in Spin City, starring Michael J. Fox as the deputy mayor of New York City. Trump plays himself, chatting with Fox’s character in a humorous exchange, blending politics and his real-life reputation as a businessman.

Fun Fact: Trump’s presence on Spin City highlighted his celebrity status in New York, long before he entered real-world politics.

5. The Simpsons (2000)

Scene: Trump was famously featured in the 2000 episode "Bart to the Future," where a flash-forward shows Lisa Simpson as the president following a disastrous Trump administration. Though not voiced by Trump himself, this episode became famous for "predicting" his future presidency and even referenced the country's economic issues under his leadership.

Fun Fact: This episode of The Simpsons gained renewed popularity in 2016 and again in 2024 as viewers looked back on its “prediction” of Trump’s presidency, calling it one of the show’s most surreal “prophecies.”

6. WWE Raw (2007)

Scene: Appearing on WWE Raw in the "Battle of the Billionaires" storyline, Trump feuded with WWE chairman Vince McMahon, culminating in a match between wrestlers representing each mogul. Trump famously “shaved” McMahon's head after winning the bet, which became an iconic wrestling moment.

Fun Fact: Trump’s wrestling cameo played into his brash, showman persona and later earned him a place in the WWE Hall of Fame.

7. Saturday Night Live (Multiple Appearances)

Scene: Trump has hosted Saturday Night Live several times, with the most notable episode in 2015 as he was running for president. Trump’s hosting style received mixed reactions, with his skits playing up his larger-than-life personality.

Fun Fact: SNL’s choice to host Trump sparked controversy but also boosted ratings, with sketches poking fun at his real estate empire, political ambitions, and larger-than-life persona.

8. The Drew Carey Show (1997)

Scene: Trump made a guest appearance in the episode "New York and Queens," playing himself in a scene where he interacts with Drew Carey’s character during a business trip to New York. His appearance was brief, but he dropped some “Trump wisdom” about wealth and success.

Fun Fact: This cameo showcased Trump’s growing appeal as a guest star in comedies, with writers often using his image as shorthand for wealth and power.

9. All My Children (1992)

Scene: Trump made a brief appearance on the popular soap opera All My Children, where he played himself. He appears at a charity event, mingling with the main characters and delivering a quick line.

Fun Fact: Trump’s All My Children cameo showed how mainstream his persona was even in the early '90s, with his appearance drawing attention to the show.

10. The Apprentice Franchise (2004-2017)

Scene: While not exactly a cameo, The Apprentice was Trump's show and arguably one of his most iconic TV roles. He became known for his catchphrase “You’re fired,” which defined his tough-businessman persona and expanded his fame globally.

Fun Fact: The Apprentice gave Trump a major boost in visibility and shaped the public’s perception of him as a no-nonsense businessman, paving the way for his eventual presidential run.

11. The Jeffersons (1985)

Scene: Trump made an early cameo in The Jeffersons, appearing as himself at a party where he interacts with George Jefferson. Trump’s appearance played into his "New York mogul" image, even at this early stage in his career.

Fun Fact: This cameo in The Jeffersons was one of Trump’s earliest appearances on TV, establishing his recurring role as the rich businessman character.

Whether you love, hate, or just laugh at Trump’s Hollywood cameos, they’ve definitely left a lasting mark on pop culture. Watching him pop up in random scenes, often as himself, is a reminder of how his celebrity status was cemented long before the White House days. Each of these scenes captures a little piece of who Trump was before politics took center stage—a media-savvy, larger-than-life figure who was always ready to steal a moment on camera.

From pointing lost Kevin to the lobby in Home Alone 2 to appearing as a socialite in Two Weeks Notice, these cameos feel almost surreal now, knowing what came next. But hey, no matter how you feel about the guy, his on-screen moments definitely add a quirky chapter to his story—and to movie history.

Stick with Woke Waves Magazine as we continue exploring the crazy intersections of pop culture, politics, and everything Gen Z needs to know.

#TrumpMovies #DonaldTrumpCameos #PopCultureThrowbacks #GenZMovies #MovieTrivia