Donald Trump’s 6 Most Heartbreaking Cameos
Sometimes you want to bask in the carefree nostalgia of an old movie when suddenly there's a Donald Trump cameo to ruin the mood.
From the late 80s to the early 2000s, it wasn't strange to be watching your favorite movie or guilty-pleasure sitcom of choice just to have the camera turn to the grinning face of Donald Trump.
How silly, you would have thought, laughing at the seemingly random cameo by the big baby billionaire, usually standing by some commercial real estate, then … forget.
Ever wonder why? Rumor has it that, for a while, to get permission to shoot at a Trump-owned location, directors needed to promise Donald Trump a part. Yes, sounds about right for a narcissist. Apparently, many of these scenes were filmed and cut before making it to the screen, but not all of them.
Now, imagine years later, run ragged by the relentless hellscape of 2020, trying to revisit your old favorite comedies for mindless comfort when suddenly the big baby himself appears. This time you do not laugh. Didn't you turn on the reruns just to avoid having to look at him—his spray tan, his lopsided wig?
Admittedly, all of his cameos are small and inconsequential—God forbid someone lay the burden of an actual plot line on Donald Trump. But despite their brevity, they're chilling reminders that it's almost impossible to escape him, even by changing the channel from the doomsday news cycle.
Maybe you like to remember a world in which Donald Trump was nothing but a celebrity millionaire, popping up in movies unannounced. Or maybe you'd like to be forewarned before retreating into a movie for an escape, just to be jolted back into our hellish reality.
Either way, here's a list of the most tragic Trump cameos—ranked in order of how heartbreaking his brief appearance is and how much he takes away from the nostalgia.
Hugh Grant and Donald Trump in "Two Weeks Notice"via Warner Bros. Pictures
Two Weeks Notice (2002)
Three's a crowd in this classic rom com, where the charming power duo of Hugh Grant and Sandra Bullock is suddenly interrupted by Donald Trump, literally. In a scene at a waterside party, Grant's character is stopped by Donald Trump for a painfully awkward moment of sword fighting. Throughout the whole scene, even a seasoned actor like Hugh Grant can't help but grimace.
Fortunately for us, this interaction is brief, forgettable, and smoothed over by Hugh Grant's ever-affable charm. This is also one of Trump's best acted cameos… probably because he's playing an obnoxious version of himself, so there wasn't much acting to be done.
All in all, this one might cause a wince but it's pretty painless. The movie is, after all, about Hugh Grant as a rich man-child, so you're primed and ready by the time Trump makes his appearance and swift exit.
Donald Trump in Season 2, Episode 8 of Sex and the City www.youtube.com
In hindsight, there's a whole host of problems with this show and Carrie is, dare I say it, kind of the worst? But all can be forgiven when you stumble across an inevitable SATC marathon in the middle of the night … except, maybe, the sudden appearance of the now-president, staring into the camera like he knows something you don't.
Trump appears in the background of a scene in the second season as Samantha grabs a drink after work. It is, admittedly, inconsequential but this doesn't make it hurt less. In a voiceover, Carrie says: "Samantha, a Cosmopolitan, and Donald Trump — you just don't get more New York than that," followed by Trump name-dropping the Tower in a moment of obvious self promotion.
A show fixated on status and celebrity, maybe it's no surprise that Trump gets a cameo. What's most painful about the scene is the conflation between Trump and New York City — a reference which definitely has not aged well.
Donald and Melania Trump in "Zoolander"via Paramount Pictures
The Ben Stiller/Owen Wilson classic is lighthearted, and slapstick at its best. Unless the idea of celebrities implicated in politics hits too close to home in this day and age, overall it's a safe bet.
The Trump cameo here is one of the most seamless. With Melania by his side, Trump appears in a montage of mock celebrity interviews in which each featured star espouses effusive praise for the title character, male model, Derek Zoolander.
If you close your eyes, you'd miss it. We recommend you close your eyes.
Donald Trump and Tim Daly in "The Associate"via Hollywood Pictures, Walt Disney Studios Motion Pictures, PolyGram Filmed Entertainment
The Associate (1996)
The moral of this 1996 Whoopi Goldberg movie: white men run Wall Street… until Whoopi Goldberg comes along.
I'll watch any Whoopi movie, but if there were one to skip it might be this one. On the surface, it's an empowering comedy about a Black woman trying to make it. Look a little closer, and there are some oversimplified ideas about workplace discrimination and racial politics. Look even closer, and you'll find Donald Trump.
Waiting for a table at an exclusive Manhattan restaurant, the movie's antagonist tries to get a seat by gesturing at his guest, Donald Trump. While he is brushed aside, Whoopi Goldberg's character enters only to be seated right away. Trump then leaves his intended party to join Whoopi and her guests.
What's most hair-raising about this encounter is that Trump is made out to be kind of a good guy. Opportunistic, sure. But there's something off about him rushing to make nice with Whoopi's character … something I can't stomach in a week riddled with news of famous Black celebrities backing his 2020 campaign.
Donald Trump shaking hands with Will Smith on "The Fresh Prince of Bel-Air" NBC
The Fresh Prince of Bel-Air (1994)
Yeah, read that again. Donald Trump was on The Fresh Prince of Bel-Air. Introduced with "esteemed pleasure," nonetheless.
In the scene, the Trumps visit the Bel-Air home with intent to buy it… much to everyone's obvious excitement. Well, almost everyone. Forever a mood, Ashley Banks (Tatyana Ali), who doesn't want to move, screams: "Thank you for ruining my life," to which Trump responds "Everyone's always blaming me for everything."
Achingly prescient, this hurts us, but it probably hurts Will Smith more.
Donald Trump in "Home Alone 2"via 20th Century Studios
Perhaps it's fitting to mention, on this day that feels like the exact opposite of Christmas—when you know you're going to get something but you're pretty sure you're not going to like it—that Donald Trump's ultimate nostalgic ruin is Home Alone 2: Lost in New York.
This cameo is pretty iconic—iconic as in so, so tragic.
Baby Macaulay Culkin (oh how much has changed) stops a random stranger to ask for directions. This stranger is, of course, Donald Trump. His appearance is brief, but it does induce some gagging at the thought of Trump being genuinely nice to children not wearing MAGA apparel.
But here's the best news: apparently they've been cutting the scene from reruns in Canada. Hoping for the day they do the same here, too.
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