The Ridiculous Stories Behind Donald Trump's Movie and TV Cameos

Before he hosted The Apprentice—and long before his short fingers came within reach of the White House—Donald Trump enjoyed a terrible and haphazard acting career.

Like Ronald Reagan, Trump's path to serious presidential candidate is littered with campy film and TV appearances. Unlike Reagan, Trump cannot actually act. And yet between 1987—when he boosted his celebrity profile with the publication of The Art of the Deal—and 2004, Trump appeared in dozens of TV shows and more than 10 feature films. Home Alone 2 and Zoolander are well remembered, but most of these movies are the kind that get lost in the dollar bin of a Blockbuster torched by its owners for the insurance money cash-in.

Speaking of cash-ins, the real estate mogul used these appearances to promote his brand: Trump nearly always played himself, with surrounding characters often stating his name in awe ("That's Donald Trump!") and remarking on his wealth. He reveled in the attention. Though Trump was a world-famous billionaire, he made himself quite available whenever an opportunity to appear on camera presented itself—even in B-movies like the ghost-sex disaster Ghosts Can't Do It. "He wasn't a hard get," says one veteran producer. "I think you can tell that as long as that gentleman got to play himself, he was up for most shows."

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Donald Trump on the set of 'Fresh Prince of Bel-Air' in 1994. Pictured: (l-r) Marla Maples as Herself, Will Smith as William 'Will' Smith, Donald Trump as Himself. Joseph Del Valle/NBC/Getty

On set, his temperament was often not so agreeable. Interviews with the directors and producers who worked with him reveal erratic and sometimes obnoxious behavior while filming. He threw a fit backstage during a Fresh Prince of Bel-Air shoot, for instance, and got extra cozy with female models on the set of the film 54. "As a producer, I found him incredibly pompous," says Eric Kopeloff, who worked with Trump for an ill-fated cameo in Wall Street: Money Never Sleeps. Kim Dempster, a filmmaker who directed him in a 2004 movie, found him to be rude and casually sexist. And Madeline Zima, the young actress from the '90s sitcom The Nanny, says Trump tried to hit on her 19-year-old caretaker when he appeared on the show in 1996.

These are the stories behind a dozen notable Trump cameos—and his ugly behavior behind the scenes.

HOME ALONE 2: LOST IN NEW YORK (1992 film)

Donald Trump's best-known movie cameo is a brief appearance in the 1992 sequel to Home Alone. The young Kevin McCallister (an abandoned child played by Macaulay Culkin) encounters him in a lavish hallway of the Plaza Hotel and asks for directions to the lobby. Trump's only line is "Down the hall and to the left." The joke, lost on most younger viewers, is that Trump owns the hotel. The cameo still surfaces today in memes.

The cameo was unplanned, says the movie's director of photography, Julio Macat. Casting director Janet Hirshenson seems to support this view: "I know nothing about how orange man got in the film," she says via email. (Neither director Chris Columbus nor Culkin were willing to comment on the experience.)

According to Macat, "He 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." Macat recalls that most of the crew was staying at the hotel during production. Trump happened to swing by during the shoot and was eager for attention. "We were the belles of the ball because of the success of Home Alone, and he wanted to hang with us," Macat says, comparing him to "a bug attracted to a bright light."

Trump was eager for attention. "He was very comfortable with the camera and kind of hammed it up for the camera," the cinematographer says. "He was supposed to just walk by, 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."

Decades later, Trump apparently is quite proud of his Home Alone involvement. In 2014, he retweeted a person telling him: "Your cameo in Home Alone 2 was some top notch stuff, you should be in more movies." And the previous holiday season, he responded to a user telling him he deserved an Oscar for the cameo with a hearty "I agree!"

THE FRESH PRINCE OF BEL-AIR (TV episode from 1994, "For Sale by Owner")

Trump's appearance on The Fresh Prince of Bel-Air is charming. His behavior backstage during the shoot was not.

The rare sitcom overshadowed by its more popular theme song starred Will Smith loosely playing himself, as he moves in with his wealthy relatives in Bel-Air. Trump (along with then-wife Marla Maples) also plays a fictionalized version of himself. In the clip, he stands around looking bemused while the sitcom characters basically throw themselves at him. At one point, Hilary Banks (Karyn Parsons, playing Will Smith's cousin) gushes at him, "You look much richer in person!" Considering Trump once edited the jokes at his Comedy Central Roast to inflate his own wealth, he probably liked this line.

According to a member of the crew—who spoke on condition of anonymity because she fears jeopardizing her current job—Trump threw a small tantrum backstage. He was holding a paper-clipped stack of pages with his lines when he became annoyed about something. He motioned as if to hand them off to Maples and, when she reached for them, threw them all over the floor so the pages went flying.

"I started to help her pick them up," remembers the staffer, "and she goes, 'I got 'em, I got them, I'm so sorry.' It was such a really rude thing, the way he did it. So terrible. So disrespectful… He just wasn't pleasant." It's not clear what Trump was mad about, though executive producer Gary H. Miller recalls being summoned to Trump's dressing room because the guest star was worried his lines weren't funny enough. "With all due respect," Miller remembers reassuring him, "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."

THE LITTLE RASCALS (1994 film)

Donald Trump was well-cast in the 1994 Little Rascals reboot: He plays the rich Rascal's dad. "I mean, he fit perfectly as the father of the spoiled brat who had no connection to the rest of the world," says Penelope Spheeris, who directed the film. "He was the perfect casting."

What Spheeris remembers most is not Trump's acting but his flamboyant arrival on set. "Usually, when people come onto the set, they're very tippy-toe, don't want to disturb anything," the director says. "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 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.'"

THE NANNY (TV episode from 1996, "The Rosie Show")

In 2016, Donald Trump insulted Rosie O'Donnell from the stage of a presidential debate. In a different universe popularly known as "1996," Trump and O'Donnell appeared on the same episode of Fran Drescher's sitcom The Nanny. (The episode opens with Drescher attending The Rosie O'Donnell Show, where she gets invited to appear on O'Donnell's show weekly.)

The episode was written by Nastaran Dibai and her late husband, Jeffrey Hodes. Dibai wasn't on set that day but remembers her husband saying Trump was "really arrogant." Madeline Zima, the actress who played young Grace Sheffield, doesn't remember interacting with Trump—she was just 11—but does say he managed to hit on her 19-year-old cousin, her legal guardian at the time. (The cousin did not respond to several requests for comment.)

Meanwhile, Trump edited the script to make him seem richer. Recalls Peter Marc Jacobson, who created the show with Drescher: "We sent the script to Mr. Trump, and in return I got a message from casting that said, 'Mr. Trump has a problem with the line above: "Do all you handsome millionaires know each other?"' 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.'"

Jacobson was so amused that he decided to frame the note. He still has it on his desk 20 years later.

Note from Trump
A memo Peter Marc Jacobson received on the set of "The Nanny" telling him that Trump wanted the script changed. Peter Marc Jacobson

EDDIE (1996 film)

Eddie was the first of two Whoopi Goldberg comedies to feature Trump, both from 1996. It's a basketball movie about a rabid fan named Eddie (Goldberg) who stumbles into a job as head coach of the Knicks, so the producers cajoled a handful of recognizable New Yorkers: David Letterman, Rudy Giuliani, Ed Koch and Trump. The cameo is just a quick man-on-the-street sound bite. "Hiring Eddie was my idea from the beginning," he says into a reporter's microphone, cocky as ever.

The movie was not well received. The Washington Post called it a "wretched roundball comedy" and noted the "slew of shameless self-promoters" who were granted cameos. Director Steve Rash isn't sure how these particular celebs were chosen, except to say, "Whoopi herself may have reached out for favors." The executive producer, Ron Bozman, recalls that the Trump cameo took all of 10 minutes to film. And though scarce direction was needed, Trump did not take direction particularly well. "He was quite, let's say, aloof about it," Bozman says. "I suggested a slight shading of delivery. He 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."

But, Bozman adds, Trump was a good fit for a cheesy, New York–set basketball flick, but maybe not for the Oval Office. "I think it would be the end of civilization as we know it."

THE DREW CAREY SHOW (TV episode from 1997, "New York and Queens")

This is a prototypical Trump cameo: A hapless gang of disposable sitcom characters end up in New York City and guess who runs into them? Trump!

The network wanted sizable cameos to promote the show's season finale, so Trump's appearance "was probably heavily promoted that week to drive the ratings," says director Brian K. Roberts. He found Trump surprisingly easy to work with. "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."

Drew Carey concurs. "I don't remember him doing anything untoward to anybody." His interactions with Trump were so brief and uneventful, he barely remembers it. "Somebody had to remind me that he [was on the show], and I was like, 'Oh shit, that's right!'" He jokes about the recent Access Hollywood leak. "We were all mic'd up, but I didn't catch anything! Believe me. I'd be the first one to put it out. Anything I can do to screw this guy over right now, I'd do it."

54 (1998 film)

If Donald Trump is looking for indie cred, he can point to his appearance in 54. Mark Christopher's 1998 love letter to the disco club era was panned on release but later hailed as a cult gay classic. The film features performances by budding stars Salma Hayek, Mike Myers, Ryan Phillippe and Mark Ruffalo. It also features an appearance by a 51-year-old Trump.

It's a fleeting cameo: During the end credits, Trump can be seen getting out of a limo and entering Studio 54. What's confusing is that the cameo appeared in the theatrical release but got nixed from both the original DVD release and the more lauded director's cut. Editor David Kittredge isn't exactly sure when it got cut; he's pretty sure the footage exists somewhere.

The movie revolves around the glamorous Studio 54, so the producers wanted to get some denizens of New York nightlife. Trump was an obvious choice. "The studio brought in a bunch of cameo folk," Christopher remembers. "Models, Sheryl Crow, Donald Trump..." The director doesn't remember much about filming Trump. "He did like he was told," he says. "But I will tell you this: He sure did like the ladies at the party afterwards. In fact, he liked two at once, as I recall."

This was at a dinner and drinks event after the shoot. The women were models, maybe extras. "The image that is burned into my memory is looking across the table and seeing Donald between two young women. He had one hand on one young woman's thigh and his other hand on the other's thigh. I thought, Hmm, how Studio 54."

SPIN CITY (TV episode from 1998, "The Paul Lassiter Story")

In the '90s, Trump could spin any cameo into self-promotion. This Spin City clip isn't an exception: In the scene, Deputy Mayor Mike Flaherty (Michael J. Fox) introduces Trump to Mayor Randall Winston (Barry Bostwick) by rattling off Trump's book titles. Spin City was a New York City show that frequently used real-life New York characters. Trump doesn't really deliver any lines here, but if you watch carefully he does show off his famous lip pucker.

"I didn't direct that episode," Fox tells Newsweek. "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."

ZOOLANDER (2001 film)

No one seems to remember that Trump had a cameo in Zoolander. Even some of the writers of Zoolander don't remember that Trump was in Zoolander. "I'd be happy to help," screenwriter John Hamburg writes in an email, "but in all honestly, I didn't even remember that Trump was in the original Zoolander. I'm guessing maybe it was during the walk-off scene?"

He's correct. It's just a five-second sound bite: "Without Derek Zoolander," Trump can be seen raving to a reporter, "male modeling wouldn't be what it is today." If there is a subliminal message in this cameo, maybe it's that Derek Zoolander's dimwittedness and crippling self-absorption is a mirror image of Trump. So, by praising Zoolander, Trump is really only praising himself.

More likely, the cameo was just an opportunistic gag. Says Hamburg: "Usually with cameos of this size, it's a matter of who we can get to show up on that day, so I'm pretty sure we did not write that into the script." Trump, as with his other cameos, was most likely unable to pass up another opportunity to be on camera. The fleeting cameo lives on—today, it's fodder for listicles like "18 Celebrity Cameos in Zoolander You Probably Forgot About." That's true. You probably did forget.

THE JOB (TV episode from 2001, "Elizabeth")

Remember The Job, the ABC drama about a crooked cop played by Denis Leary that aired for two seasons before being canceled in 2002? Trump had a cameo in 2001, appearing opposite model Elizabeth Hurley.

Hurley, then recently split from Hugh Grant, was a big draw for Trump, according to the episode's director, Tucker Gates. "When he first came to set, I went up and introduced myself: 'Mr. Trump, it's nice to meet you.' And he just looked at me and said, 'Where's Liz?'" Gates remembers. "Well, Liz is in hair and makeup, and she'll be out in half an hour," the director responded. Trump asked how long the scene would take to shoot. "Probably about three hours." Trump shot back: "I got 20 minutes." (Of course, he stuck around for longer.)

The clip is creepily prescient in light of Trump's brags about kissing and groping women without consent. In the scene, he spots Hurley dining out with a male companion (played by Leary) and shares a friendly cheek-kiss with the model. "Donald owns this restaurant," Hurley tells Leary, at which point Trump bluntly asks the guy if he's sleeping with her, then gives Hurley a much more seductive kiss and tells her to call him instead.

"I think he was enticed to be in a scene with Liz," says the director with a laugh. "I don't remember him being difficult. I just remember him being focused.... He obviously was not an actor but wanted the publicity as well." The writers scripted the episode with Trump in mind thinking they'd never get him. "[We] were unaware as to the length and breadth of his self-whoredom," says TV veteran Peter Tolan, who wrote the episode with Leary. "A chance to be on camera? Of course he said yes!" (Gates seems to recall that Leary was trying to get an apartment in Trump Tower at the time, making an encounter with Trump particularly appealing.)

As for the Donald's 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."

MARMALADE (2004 film)

Filmmaker Kim Dempster asked Donald Trump to appear in her 2004 romantic comedy Marmalade. She didn't enjoy the experience. "I remember leaving and saying, 'I don't like him,'" Dempster says. "I didn't enjoy it at all, which is weird. I like to shoot."

The movie is about a fashion model who ages out of her profession. Dempster decided she wanted real-life agency bosses as well—the darker side of the industry. She thought of Trump, who'd recently launched his own modeling agency, Trump Model Management. Asked what it was like to film him, Dempster has a lot to say. "First off, he was very hard to shoot because he's got this crazy hair, [and] he won't let anybody touch it," the filmmaker says. "It was really big back then. It looked like some weird wig."

As a female filmmaker, Dempster is accustomed to a male-dominated industry. But Trump's arrogance sticks in her memory.

"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."

WALL STREET: MONEY NEVER SLEEPS (2010 film)

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Donald Trump was supposed to appear in 'Wall Street: Money Never Sleeps,' but the cameo was cut from the movie. The film stars Shia LaBeouf and Michael Douglas. 20th Century Fox

It's almost too on-the-nose: Trump, whose cameos often play up his obscene wealth, agreed to appear in a movie about corporate greed that is literally subtitled Money Never Sleeps. It didn't work out. As Wall Street director Oliver Stone recounted during a Q&A at Comic-Con International, Trump's cockiness made filming difficult, and the director cut the cameo from the final film because he found it "distracting."

The story behind the ordeal now seems more compelling than the cameo itself. Producer Eric Kopeloff says his team dreamed up the Trump cameo when they were reaching out to various finance figures and luminaries to consult on the film. "It was considered a comedic thing," says Kopeloff. "Now, I don't know if Donald Trump understood that." The scene would take place in a barbershop. Gordon Gekko (Michael Douglas's famous character) finds himself in a barber chair seated next to Trump.

"Of course, when [we approached] Donald Trump, the guy responds like right away," Kopeloff recalls. "'Through his people, not him directly: 'I'd love to do it. That would be amazing.'" (This is the thing about Trump the Cameo Actor: He's never a hard get but rarely an easy shoot.)

The shoot with Trump was set for June 5, 2010. The producers chose a design barbershop on the Lower East Side of Manhattan. Around 6 a.m., the crew started setting up. And 45 minutes later, the email arrived.

It was a memo from Trump's assistant containing ridiculous instructions for how Trump should be lit ("no red tones please"), shot ("camera eye level or above") and depicted ("warm golden tan skin and a more defined jaw-line").

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An email sent from Trump's office to the producers of "Wall Street: Money Never Sleeps." Eric Kopeloff

"It was absolutely absurd!" Kopeloff recalls. "'He should be shot like this! The lighting should be like this! You can only shoot him from this side of his face to make his golden hair glow.' It's so absurd. We shot all these people. All these luminaries! You can look and see the movies I've made. All these movie actors. Never, ever, have I seen anything like this. Not from the biggest movie stars in the world! It was like you're going back to the 1940s and getting a note from the head of the studio.

"So the email comes in. Also, he wants his own separate monitor so he can see what he looks like right after being shot. First of all, this is an Oliver Stone movie. Second of all, it's a movie. The movie is about Michael Douglas, Shia LaBeouf, Susan Sarandon. It's not about Trump." The producer gets agitated just thinking about that email: "Are you kidding me? Are you absolutely out of your mind? This is a movie! What are you talking about?"

The filmmakers largely ignored the Trump team's demands, but they couldn't ignore Trump's terrible acting.

First, the Donald showed up a little late, which Kopeloff found "ridiculous." Oliver Stone got him ready for the scene. After the first take, he turned to Stone and exclaimed: "Oliver! Wasn't that great? Wasn't that amazing? Oh my God, that was so great!" Stone replied: "Yeah, yeah, it was very nice. Let's just do it again," according to Kopeloff's version of events.

"Oliver's a very respectful guy," Kopeloff says. "He's not gonna say no. But it wasn't good! It was awful! 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, 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."

Other complications made working with Trump a nightmare. For one, Trump's team reportedly insisted on a contract banning the hairdressers from touching his hair. For another, paparazzi showed up to snap photos of the shoot, leading the producers to suspect that Trump may have tipped them off. ("The way I look at it, the guy obviously let them know where he's going to be, so he can get that photo op.") The cameo was ultimately shelved.

Kopeloff found the experience exasperating but indicative of Trump's religious devotion to his own self-image.

"It's so much about him," he says. "Trump is about Trump is about Trump. He is not interested in anybody else around him. He wants to be the center of attention. But in all reality, at that point, he just comes off like a buffoon. I found that, for a guy who was a television personality, he didn't have the chops to deliver what he needed to deliver, which was pretty simple."

* * *

Trump's cameos are a bit like his presidential campaign: impulsive, ill-advised and shamelessly devised to promote the Trump brand. The GOP nominee's hunger for attention is his defining characteristic—whether on a debate stage or driving a limo through the set of the Little Rascals. He'll say yes to any director who wishes to point a camera at him, and he'll retweet any Twitter account that says he is winning, even "@WhiteGenocideTM."

With few exceptions, many of the producers and directors who worked with him describe the man as abrasive if not outright hostile. (His behavior reportedly grew even coarser and more overtly sexist on the set of The Apprentice.) And yet for years, Hollywood shoved Trump's face into movies and TV shows. In several instances (Little Rascals, the forgotten IMAX flick Across the Sea of Time) the filmmakers didn't necessarily want to work with Trump. The order was passed down from the executive suite—"How about putting Trump in the movie?"—because he's a recognizable beacon of New York, because he's outrageous, because, well, people just find the guy entertaining. They still do. Which is how Trump landed his weirdest cameo yet: on an election ballot.

Correction: An earlier version of this story referred to the disco club in 54 as Club 54. The correct name is Studio 54.