With the election only weeks away, it’s increasingly difficult to turn on a TV without seeing Donald Trump’s distinctive orange-ish face. But while his foray into politics has certainly increased his visibility, it’s far from the first time that Trump’s been on screen.
The tycoon is famous for his reality show The Apprentice, a twist on the classic talent contest that has Trump judging contestants’ business acumen rather than, say, singing ability. Even before the show launched in 2004, Trump was no stranger to the cameras. He’s appeared in a surprising number of movies and sitcoms in addition to the reality and talk shows that he is famous for. Past master at self-promotion, he often finds himself playing his favorite role: himself. From bit parts to big scenes, we’ve rounded up the fifteen most interesting occasions in which the Republican Presidential Candidate has played himself on screen.
Eddie (1996)
Whoopi Goldberg stars as the titular Eddie in this mid-nineties comedy about a New York limo driver who wins a contest to be the New York Knicks’ ‘honorary coach’. It’s a simple feel-good flick, where Eddie turns the team around with her understanding and no-nonsense attitude, only to find that the team is now doing so well that they could be sold to a group that will move them to St Louis. Obviously, Eddie saves the day and the team stays in NYC and continues to succeed, thanks to her coaching.
Trump appears to take credit for Eddie being hired on as full-time coach after she won the contest – even though he had absolutely nothing to do with it! His line in the comedy is “hiring Eddie was my idea from the beginning”, even though we all know that it was Wild Bill Burgess (Frank Langella) who gave Eddie her shot. A mediocre cameo in a distinctly mediocre sports comedy, Trump was more than happy to poke fun at himself in this lighthearted ’90s throwback.
The Associate (1996)
The same year that Eddie came out, Whoopi Goldberg starred in another comedy as a woman breaking down societal expectations – only this time, it’s not on a basketball court. In The Associate, Whoopi plays Laurel, a fantastic investor sick and tired of the old white men she works for taking all the credit for her hard work. She starts up her own firm, but when no one wants to hire her, she decides to pretend to have a white male partner to convince them to bring her on board.
Laurel and her firm are quickly becoming the new rising stars of finance, and Trump pops in as he waits with her ex-boss Frank (Tim Daly) to get a table at an exclusive restaurant. While Frank is stuck waiting, Laurel and her client breeze past to be immediately seated at the fictitious Cutty’s usual table, and Trump decides to join them. In this scene, Trump is just a big name to show how well Laurel and her firm are doing – and to stick it to her old colleague in the best possible way!
The Nanny - “The Rosie Show” (1996)
In 1996, Trump had a cameo on The Nanny, a simple sitcom about a beauty product saleswoman who ends up as nanny to the children of a rich businessman (no prizes for guessing that they end up falling for each other). A lighthearted comedy starring Fran Drescher, The Nanny saw Trump appear as himself in ‘The Rosie Show’, where Fran gains some unexpected fame after being pulled from a TV audience, and meets Trump along the way.
As with most of his on-screen moments, Trump has only a couple of lines, and the bulk of the comedy is built around his presence rather than anything he says or does. In this case, he is introduced to Maxwell (Charles Shaughnessy) before telling Fran that he’ll go wait in the limo. On his way out, his cell phone rings, and he picks it up with “I told you never to call me on this line”. He hangs up, only to have another cell phone start ringing in his other suit pocket. Trump answers that one with “that’s better”, a simple gag to show off that not only that he is two-cellphone rich, but that he is powerful enough to make this kind of nonsensical demand just because he can.
Night Man - “Face To Face” (1997)
It’s not surprising that few people are aware of this cameo, as the show itself is a so-bad-it’s-good superhero series from the late ’90s that is better off forgotten. Night Man introduces us to a new hero, Johnny Domino (Matt McColm), a man who is telepathically tuned to ‘evil’ frequencies after being hit by lightning. He uses this ability to home in on criminals and stop them in their tracks, while wearing a (hilarious) blue and black muscle suit and mask.
Trump appears in “Face To Face”, an episode about a shapeshifting criminal who can make himself look like anyone he wants – including rich businessmen. He uses this power to ‘become’ Trump in order to steal money from the mogul at his bank (before Night Man stops him, of course). The real Trump, meanwhile, uses the show for some painfully obvious product placement of his book, though he probably could have picked a better show to do it in.
Zoolander (2001)
In 2001, Trump made a brief appearance in Zoolander as one of many famous faces to join the cast of this silly comedy about a clueless fashion model. Trump has a single line, as he is interviewed at the VH1 fashion awards about Derek Zoolander (Ben Stiller): “Without Derek Zoolander, male modeling wouldn’t be what it is today”. Melania Trump also appears in the shot, standing silently by his side in a shiny dress.
Other celebs who were also featured in the backstage-interview-style cameos included designer Tom Ford, Victoria Beckham and Emma Bunton (Posh Spice and Baby Spice from the Spice Girls), Christian Slater, Cuba Gooding Jr, Tommy Hilfiger and a very shiny Natalie Portman. It’s one of his least stilted roles, as he is not just playing himself, but doing so in what has to be a familiar space – with a microphone in his face and his latest wife by his side.
The Drew Carey Show - “New York And Queens” (1997)
Here we have yet another sitcom appearance, but Trump’s cameo on The Drew Carey Show stands out because this time, he’s still playing himself, but not as a brusque businessman, a boardroom shark, or a generic “rich and famous” type. Instead, the Trump we see here is surprisingly nice. In the episode, Drew (Drew Carey) and his friends are stuck in a traffic jam in New York City on their way to a Yankees game when Donald Trump strolls by. Although they start off a little rocky (with Trump asking for an ice cream, and the friends explaining that their ice cream truck is actually stocked with beer), Trump actually ends up offering them the use of his skybox to go watch the ball game – a pretty incredible gift to a group of total strangers on the street!
He cracks some jokes about the traffic and tells them he’ll come back for a beer, all but balancing out his abrasiveness when he first meets Drew and the gang. He calls them all morons and sarcastically says “it’s weird, isn’t it? Sort of like I’m human.” when Drew is surprised to see such a celebrity.
The Little Rascals (1994)
Everybody loves The Little Rascals, and everybody hates one kid in particular: Waldo (Blake McIver Ewing), the bratty, snobbish rich kid who was Alfalfa’s (Bug Hall) nemesis and competed with him for the affections of Darla (Brittany Ashton Holmes). Waldo is the obnoxious villain of the movie of course, complete with a fancy go-cart paid for with daddy’s money (compared to the one the ‘He-Man Womun Haters Club’ built with love) and a tendency to wear suits and slick back his hair.
He’s also got an obnoxious, rich dad, played here by The Donald. Trump appears in one scene of the movie, as Waldo is driving his go-cart and calls his Dad to boast that he’ll win the race. (A scene that meant a lot more in ’94, when most adults didn’t yet have a cell phone.) Trump tells Waldo that he is “the best son money can buy”, a line that is obviously meant to hammer home just how spoiled and wealthy they are.
Suddenly Susan - “I’ll See That And Raise You Susan” (1997)
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Another ‘90s sitcom appearance, Trump’s cameo on Suddenly Susan saw him at a poker game with the guys (and not even in the same room as the title character, sadly). Sitting down with John McEnroe, politician Willie Brown, and Judd Nelson (as Jack Richmond), the gag is all about how rich Donald is compared to the other divorcees at the table. When Jack tells the other players that whatever he wins will be the only income he has not garnished by his ex-wife, Trump tells him “I hope you have a good lawyer”, to which a third player replies with a joking reminder that Trump is rich… and it’s only fifty cents to open.
Trump’s final line before play commences? “…and I didn’t get rich by throwing away quarters”. Essentially, this cameo is just to show off how rich Trump is, with the whole gag being based on the incongruity of a millionaire at a low-stakes poker game (that turns into a bottle-cap tossing contest).
Spin City - “The Paul Lassiter Story” (1998)
Trump does some more book promotion on Spin City, in an episode titled “The Paul Lassiter Story”. A sitcom about local politics, Spin City doesn’t see Trump appear as a politician (at the time, that was so unfathomable that The Simpsons even cracked a joke about it!), but as a best-selling author.
Mayor Randall (Barry Bostwick) has a book to write, but his usual right-hand man isn’t too helpful… so he brings in Donald Trump to give the Mayor advice on how to write a book. The scene opens with the mention of both Trump’s book titles (The Art of the Deal and The Art of the Comeback), just in case the push wasn’t clear enough to a casual viewer, before continuing to give the mayor some help. The Art of the Comeback had just been published the year before, and is introduced with the line “and then he wrote a new bestseller”, making this one of Trump’s more straightforward TV plugs for his own brand.
Home Alone 2: Lost In New York (1992)
One of Trump’s smallest on-screen roles – he has only a single line in Home Alone 2: Lost In New York – this is easily is best-known movie or TV cameo to date. The sequel to the hugely popular Home Alone finds the hapless Kevin McCallister (Macaulay Culkin) on his own in the Big Apple, where he finds himself having a better experience than most tourists who are there intentionally!
He stays at the Plaza while he is there, and even manages to bump into Donald Trump while looking for the lobby. Trump, who goes unrecognized by our perpetually parent-less hero, directs young Kevin “down the hall and to the left”, before looking perturbed that the young boy doesn’t know who he is. Of course, Trump actually owned the Plaza when the film came out in 1992, although that was the same year in which the landmark ended up in bankruptcy protection thanks to Trump’s $50 million renovations that the hotel’s earnings couldn’t balance out.
Two Weeks Notice (2002)
Rom-com royalty Hugh Grant (as George Wade) and Sandra Bullock (as Lucy Kelson) star in this 2002 film about a neurotic lawyer who falls in love with her rich, charming, and morally questionable client. In classic rom-com style, of course, the two can’t stand each other when they first start working together, so Lucy gives her two weeks notice. As she helps George look for her replacement, she slowly realizes that she doesn’t want to be replaced.
Trump appears at a party scene where he obviously already knows George. Similar to many of his other cameos, Trump appears as the token rich guy who already knows the fictional rich guy. In this appearance, he asks George about Lucy leaving him (giving Hugh Grant the chance to do his floppy-haired, self-deprecating best) before threatening to steal her replacement. He wraps up the appearance by strolling away as George continues to mumble away.
The Job - “Elizabeth” (2001)
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In this crime/comedy series, Denis Leary is Mike McNeil, an alcoholic, adulterous, and (of course) unconventional New York detective. His misadventures fighting crime and his own personal demons form a semi-satirical take on the usual cop dramas of the era.
Trump appears in the second episode of the short-lived series, when Mike is out to dinner with Elizabeth Hurley (also playing herself). The mogul owns the restaurant they eat at, and comes to greet them at the table – where he proceeds to behave appallingly. After giving Elizabeth a kiss and telling her she looks great, he is introduced to Mike… and immediately asks “are you banging her?”. Mike looks as shocked as you would expect from such a blunt and off-putting question before he manages to reply that they’d just met. Trump, after pressing for an answer, then completely ignores Mike to kiss Elizabeth again and tell her to call him. It’s a study in how not to behave around a woman, and Trump nails it.
Ghosts Can’t Do It (1989)
Ghosts Can’t Do It saw Bo Derek star as a widow whose husband is a ghostly presence in her life attempting to convince her to kill a man (so that the dead man can come back and possess his body, naturally). Trump appears as himself as he goes up against Derek’s Katie Scott in a business meeting where she is aided by her husband telling her what to do. It’s a scene that doesn’t lack for misogynistic moments, including plenty of emphasis on the fact that Scott is gasp a woman.
Trump’s major line, however, is more bizarre than sexist, and it’s followed by some serious pouting. “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”. Trump actually won an award for his brief appearance in this downright terrible crime fantasy movie from 1989 – a Razzie, for Worst Supporting Actor. He was actually nominated for two Razzies, but lost out on Worst New Star to Sofia Coppola for her role in The Godfather: Part III. It’s probably not the sort of statue Trump was looking to acquire when he began his acting career, but it’s something.
Sex And The City - “The Man, The Myth, The Viagra” (1999)
In 1999, Trump made a brief appearance in the raunchy, feminist (for the time) HBO series, Sex And The City. In an episode titled “The Man, The Myth, The Viagra” (cue groan), the focus of the episode was the urban myth of the man who suddenly changes into the perfect boyfriend. The secondary storyline, meanwhile, centered on Samantha’s (Kim Cattrall) fling with a much older man.
For Samantha, his millions upon millions of dollars were almost enough to balance out her total lack of physical attraction – but not quite. Trump shows up as the business associate of Samantha’s elderly conquest when the two first meet. She notices the two men as she sips a cocktail, as the voice over informs us, “Samantha, a cosmopolitan and Donald Trump. You just don’t get more New York than that”. In a show filled to the brim with cringeworthy moments, this one is…surprisingly tame.
The Fresh Prince of Bel-Air - “For Sale By Owner” (1994)
In 2016, Will Smith is an A-list celebrity who has made it abundantly clear that he’s not a Trump fan. In 1994, however, Smith worked with the businessman on an episode of his still completely hilarious series, The Fresh Prince of Bel-Air. “For Sale By Owner” revolves around Trump and his then-wife Marla Maples, as the mogul offers to buy the Banks’s home.
The episode itself isn’t one of the better ones in the series, as it’s a dreaded flashback episode where the family thinks back on their history with the house. Trump himself appears briefly toward the end in order to see the house after the Banks have decided to take the money. He and his wife stride in, causing Carlton (Alfonso Ribeiro) to fangirl so hard that he actually faints (who doesn’t love Carlton-the-dork?). The best moment, however, is when Ashley (Tatyana Ali) is furious with Trump, and yells at him for “ruining her life” – which he promptly brushes off with a wave of his hand and a line that he’s probably reiterated on a few occasions this year: “Oh, everybody is always blaming me for everything…”.
What other shows and films has Trump appeared in as himself? Let us know in the comments.
