One of the most promising things about Donald Trump‘s presidency is that the world might get to enjoy more cameos on television and film from the man. In recent years, basically ever since The Apprentice, Trump’s cameos, which used to be semi-regular, dwindled away. Nowadays, film and television fans are forced to look back and recall the times when the real-estate mogul would appear in random places on TV all the time. For the most part, his cameos were similar. Trump would appear and people and the main cast members would gush, often saying something to the effect of, oh my God! It’s Donald Trump. He’s rich. Trump, if he had lines, would usually be short and to the point. He would mention money and business. In fact, for many of his cameos, the Donald would be engaged in business during his cameo.
We see these similarities and we wonder why Hollywood can’t be original. Mix it up a bit. But there’s a reason why these cameos are all so identical. These were the Donald’s demands. In exchange for being available for really any TV show or film at any time, Donald had a list of requirements. In the early days, it was all about brand recognition for Trump. The more people saw him and heard his name in connection with business, wealth and real-estate, the more his brand power increased. Later on, Trump’s camp would send directors more explicit instructions, like the need to use a “warm golden lighting,” a final shot that highlighted his “warm golden” skin tone, and an angle that accentuates his “defined jaw-line,” while avoiding the hair part on his left side. Yet despite these limitations, Trump’s had some magical cameos over the years. Let’s take a look at the best of the bunch. Here are the 15 Best Trump Cameos in a Film or TV show.
15. Home Alone 2: Lost in New York
Due to the popularity of the film, Donald Trump’s cameo in Home Alone 2: Lost in New York is probably his most famous. Yet, aside from Trump’s beautiful delivery of the line, “down the hall and to the left,” the most amazing thing about this cameo is that it was entirely unplanned. Julio Macat, the film’s director of photography, explained that “[the Donald] showed up on the set, and Chris [Columbus] thought it’d be fun to put him in. We were all nice to him because he owned the Plaza Hotel, and we were filming there.” The story goes that Trump was quite the showman too. He even improvised his part to improve on his short appearance. “He was supposed to just walk by,” Macat said, “but he walked by and then turned and threw a look towards the kid…. I remember being amazed at how this guy knew where the lens was.” Now that’s acting.
14. Ghosts Can’t Do It
In what would turn out to be one of Trump’s largest cameos, his appearance in Ghosts Can’t Do It with Bo Derek is also one of his best. The film itself is a treat to watch, especially if you’re a fan of truly terrible movies. Trump plays himself, one of several menacing businessmen. In his big scene, Trump and Derek square off in a board room and Trump delivers the line, “Be assured Mrs. Scott, that in this room there are knives sharp enough to cut you to the bone and hearts cold enough to eat yours as hors d’oeuvres.” Then something strange happens. Derek, a woman who was long considered one of the world’s biggest sex symbols, says, “You’re too pretty to be bad.” Donald makes a kissing face, or a duck face, we’re not quite sure. But the curious thing is that we realize from this interaction that Donald is meant to be a sex symbol himself. Or was it just Derek using her alluring strengths? Either way, Trump received an award for this performance. Not as significant as the major award in A Christmas Story, but we’re confident that the Supporting Actor Razzie is something Trump cherishes.
13. The Little Rascals
In The Little Rascals, Trump plays Waldo’s father in a brief clip. Yeah, we know this isn’t technically a cameo because he’s playing a character, but he’s the exact same Trump as always, so we’ll allow it. It’s actually a funny scene. The pompous Waldo (Blake McIver Ewing) calls his dad on a cell phone in the middle of the race and tells him he’s going to win it. Trump responds, “Waldo, you’re the best son money can buy.” Apparently, Trump’s arrival for the cameo was an even better performance than what was shown in the film. The director, Penelope Spheeris, said, “Usually, when people come onto the set, they’re very tippy-toe, don’t want to disturb anything… Here’s how Donald Trump came onto my set. It was a sea of crew members, standing around the camera, and all of the sudden the sea parted and a limo pulled through them, carefully managing not to hit anybody, and pulled up right next to where the camera was placed. He stepped out of the car and waved to everybody in the grandstand, like the Rose Queen would do. I thought, How audacious of this person! And then Marla [Maples] got out after him. They acted like the king and queen of England. I was like, ‘Can we get this limo out of the way, please? I’m shooting.’” In other amazing news, look at those brows.
The movie Eddie, is that odd Whoopi Goldberg film in which a random fan, Eddie (Whoopi), wins the chance to coach the Knicks for half a game after sinking a half-court shot. Because she’s popular with the fans, the Knicks’ owner hires her as the coach full-time. At some point, Donald Trump is interviewed on the streets of New York about the hiring and he says, “Hiring Eddie was my idea from the beginning.” The cameo is short and sweet, but, behind the scenes, Trump and some of the crew didn’t see eye to eye. Ron Bozman, one of the producers of the film, said, “I suggested a slight shading of delivery,” and Trump “looked at me like I was a total idiot. He looked at me like, ‘Nobody tells me what to say.’ He was arrogant about taking any direction.”
11. Sex in the City
Trump’s cameo in Sex in the City is one of the strangest on this list. Perhaps his only reason for showing up was to be connected with the image of New York, but it’s strange for a number of reasons. While Samantha (Kim Cattrall) makes eyes at two men sitting in the back of the bar, we see that one is Trump and one is a man who must be in his 70s. Suddenly, Trump leaves and says something to the effect of, “I’m Donald Trump and I’m leaving to go to Trump Tower.” Then Samantha and the 80-year old begin to flirt. How could you pass up on the Donald Samantha? Bad choice.
10. Wall Street: Money Never Sleeps
Sadly, Trump’s cameo in Wall Street: Money Never Sleeps never made the final cut of the film, but we can still watch it in all its glory online. The scene took place in a barbershop and included a joke about a combover. It was the best scene in the movie, but they cut it out because the director, Oliver Stone, found it distracting. While Stone didn’t have too much to say about it, Eric Kopelof, one of the film’s producers, had strong feelings about it. After shooting one take, Trump thought they were done, but Kopelof saw something different than the businessman. “It wasn’t good! It was awful!” he said. “I’m the producer of the movie—I have the headsets on. He’s awful! It’s terrible! Horrible! And we do it again. But after every single take, it’s the same thing: ‘Wasn’t that amazing? Michael [Douglas], wasn’t that great? It was so great! Great, great, great!’ Oliver goes, ‘Yeah, it was good. Let’s try it a little bit this way. Let’s try it a little bit that way.’ I think we had a couple different shots that we were gonna do, maybe different angles, maybe different jokes. But after about nine or 10 takes, I think it was very clear to all of us—and it wasn’t spoken—that we were done.”
9. Two Weeks Notice
In a phenomenal cameo in Two Weeks Notice, starring Hugh Grant and Sandra Bullock, Trump appears at a party and he and Grant’s character talk shop for a minute. Trump asks about Grant’s new chief counsel (Bullock) saying, “if she’s any good, I’m going to steal her away.” This is the Trump we all know and love. Strong and self-assured, a true ladies’ man. When Grant suggests that Bullock’s character is loyal to him, Trump says with a smirk, “Let me be the judge of that.” With that he leaves to go and grab her. Attention. He leaves to grab her attention.
When Zoolander came out in 2001, Trump had already founded Trump Model Management, so it made sense for him to make a cameo, associating himself with the world of modelling. During the in-film interview, Trump says, “look, without Derek Zoolander, male modelling wouldn’t be what it is today.” But Trump didn’t need a business interest in models to appear in this film. He’s long been personally interested in models. His first wife, Ivana, was a model. Ex-wife Marla Maples has done some modelling, and, of course, Melania, the first lady of the United States, is a former model. In another Trump cameo, 54, the film’s director, Mark Christopher, claims that Trump liked the models there too. In fact, “he liked two at once,” the director said.
7. Fresh Prince of Bel-Air
When Trump shows up to buy the Banks’ home in Fresh Prince of Bel-Air, Carlton (Alfonso Ribeiro) passes out from excitement, an expected reaction to coming so close to greatness. Donald makes a hilarious joke about wanting to “keep a low profile” and then a quip about bringing cash in a briefcase to buy another home because “it’s quicker.” His then-wife, Marla Maples, does most of the talking for them, but Trump glows on camera. The stories behind the cameo aren’t as flattering as the shots though. Apparently, Trump was upset that his lines weren’t funny enough, so he threw the script on the ground, scattering papers everywhere for Maples to pick up. When one of the show’s producers, Gary Miller, was called to Trump’s dressing room to address the issue, he said to Trump, “I would never think of giving you any advice about real estate, because I don’t know about real estate. But I do know comedy—and trust me, you’ll get a laugh.” It worked. Trump was hilarious.
6. The Nanny
In a quick but memorable scene in The Nanny, Fran Drescher brings Trump home with her. Trump does some business in the scene, answering two different cell phones, looking like the boss we know he is. Show creator, Peter Marc Jacobson, tells a story that, when he first sent the script to Trump, it had the line “Do all you handsome millionaires know each other?”’ Trump sent back the script saying he had a problem with the line. Jacobson said, “I was actually impressed and thought, ‘Isn’t it nice that he’s humble and doesn’t want to call himself a millionaire?’ Then I read the rest of the note, and it said, ‘Since he’s a billionaire, he would like the line changed accordingly.’” The line was changed to “zillionaire” to accurately reflect Trump’s wealth.
5. Spin City
While most of Trump’s cameos mention how rich he is and something about business, only his appearance in Spin City with Michael J. Fox specifically plugged two of his many books, The Art of the Deal and The Art of the Comeback. It’s not necessarily the most memorable of Trump’s cameos, but we love it. So does Trump. When Fox was asked about it, he said, “My memories are not of Donald Trump’s appearance on the show so much, but of how every time I’ve seen him since he reminds me of how good the ratings were for that episode. The funny thing is, I don’t think the ratings were so good that week.” Yes, they were Michael. Yes, they were.
4. The Job
In the show The Job, starring Dennis Leary, there was an episode in which Leary’s character goes out with a woman played by Elizabeth Hurley. It turns out that Trump is a big Hurley fan and was eager to work with her in the cameo. In the scene, Trump interrupts the date and ends up kissing Hurley twice. When he first came on set to shoot this masterpiece, the director, Tucker Gates recalls saying, “Mr. Trump, it’s nice to meet you.” Trump, however, “just looked at me and said, ‘Where’s Liz?’” Peter Tolan, one of the show’s writers, said of Donald’s acting talent, “I can simply sum up his acting ability to say that he was not a natural,” says Tolan. “He had very little to do. And what little he did, he did very stiffly.” Sometimes greatness is misunderstood.
As we’ve seen, many of Trump’s cameos have some strange backstories attached to them. The man has a giant personality and sometimes that seems to rub people the wrong way. In his Marmalade cameo, Trump plays Trump in a very straightforward scene, but the director, Kim Dempster, struggled with it. “First off, he was very hard to shoot because he’s got this crazy hair, [and] he won’t let anybody touch it,” she said. “It was really big back then. It looked like some weird wig.” Although it doesn’t sound like he did anything wrong, Dempster didn’t like Trump much after working with him briefly. “I left, and I said to somebody, ‘He’s a sexist,’” she remembers. “But he didn’t do anything. It wasn’t like that. It was more of, I wasn’t equal. That kind of sexism. Not what’s in the news right now. More of ‘She’s not important. She’s just a woman.’ That’s the feeling I got. Which is really horrible.”
2. The Drew Carey Show
In what would become Trump’s most likeable cameo, his spot in The Drew Carey Show came in an episode that has Drew and friends visit New York City to watch the baseball game. Stuck in the city’s traffic in their ice cream truck, Carey and friends see the Donald, who mistakes them for selling ice cream. Even though he calls them “morons,” Donald gives the group access to his box seats to watch the game. He comes out of the cameo looking like a proper gentleman, a very rich proper gentleman. Brian K Roberts, the show’s director, had only nice things to say about Trump. “I met the Donald Trump that you hear about—but you don’t seem to see an awful lot of. He was easy to direct. He took direction very well. He was on time…. He’s not the world’s greatest actor or anything. But he certainly was serviceable.”
1. WrestleMania 23
Alright, it’s not a TV show, but we’ll be damned if Donald’s appearance in WrestleMania 23 doesn’t make the list. It was the “Battle of the Billionaires,” Vince McMahon vs. Donald Trump. Well, really it was Intercontinental Champion Umaga, accompanied by Vince McMahon, vs. the ECW Champion Bobby Lashley, accompanied by Donald Trump. The fight was going as planned until Trump viscously attacked McMahon, taking him to the ground and pounding on him relentlessly with the fury of a lion. After winning the right to shave McMahon’s head bald, and taking full advantage of it, Trump was then given an incredible stunner from guest referee Stone Cold Steve Austin. It was a TV moment that may go down as one of the top five things ever seen on screen.