A Monster Begat by Cameos: Trump Was Glorified in the Media Long Before Negative Coverage Plagued His Presidential Run

“The Donald,” a name that once sounded endearing when it came from Ivana Trump but now sounds more fittingly like the epithet of a horrific monster, has made many appearances in pop culture before his oversaturating, overexposed presidential run. And it is, in many respects, this sort of aggrandizement of the mogul in film and television that has only helped to cultivate the beast (not in the good, Alyssa Edwards sense of the word) that has now risen to one of the most prominent positions of power in the world. Below are the five most memorable times in film and television when he was painted as a false legend, solely in NYC settings–a city that represents everything most of what the rest of America loathes:

Sex and the City: In a season two episode fittingly entitled “The Man, The Myth, The Viagra,” Trump appears at a restaurant where Samantha first meets a rich older gentleman, Ed (Bill McHugh), who she eventually agrees to sleep with because, well, he’s rich. The presence of Donald serves to highlight 1) Ed is powerful and 2) Donald is a New York City institution (after all, Sex and the City was all about the local celebrity–including the name check [e.g. Ed Koch]).

Home Alone 2: Lost in New York: This rare treasure of a sequel is now only sullied by just one thing–Trump. Re-framed in the wake of his current stature, Donald looks like a creepy pedophile eyeing Kevin McAllister (Macaulay Culkin) up and down as he lingers by the Plaza Hotel, yet again iterating the point that the only thing a Donald cameo is good for is to accent his wealth and power.

Zoolander: What would a movie parodying the very nature of superficiality and meaninglessness be without the double whammy of a cameo by both Trump and his possibly stuffed animal wife, Melania? Though it might have been a bit more just for Trump to have appeared in the inferior sequel, his presence in a film that accents how American culture promotes vying solely for the perfunctory aspects of success is undeniably appropriate.

The Nanny: In a strange twist of retroactive irony, Trump shows up on an episode in season four of The Nanny called “The Rosie Show,” wherein Fran (Fran Drescher) gets invited to give regular parenting advice on The Rosie O’Donnell Show. Donald materializes after Fran finds herself becoming a bit of an NYC celebrity herself. Recurrently, the storyline Donald fits into stresses the importance of affluence, and its unbreakable bond with power. The consistent tableau makes it all the more clear that the American presidency is up for grabs to anyone who can afford it.

Celebrity: Woody Allen’s polarizing 1998 film (aren’t they all post-Crimes and Misdemeanors?), Celebrity, is an eerily titled vehicle for Trump to grace his chaff with. In truth, it’s hard to know how much of Donald’s so-called prosperity has been a result of his business acumen or his ability to play into the caricature that has become his real life persona. Though Allen doesn’t portray Trump in a favorable light (which, as usual, never seems to bother the 45th president), he is, once again, given the cloak of untouchable influence with a plotline that sees him planning to buy Saint Patrick’s Cathedral so he can tear it down–this now has some rather unsettling metaphorical value, as it’s pretty clear he’s just bought America and is about to fucking demolish it.

And so, though many may wonder how Donald Trump suddenly came to land one of the most eminent roles in history, look back to how readily pop culture was willing to showcase him as a heavyweight.