Today, it would be extremely odd to compare a man to Donald Trump, the leading contender for the Republican nomination for president who has built his campaign on nativist platforms and ugly rhetoric, as a way of saying that he’s highly eligible. But long before “The Apprentice,” Trump’s business reality show, or his involvement with the Miss Universe pageant, Trump was a pop culture icon, appearing in everything from “The Fresh Prince of Bel-Air” to Woody Allen’s “Celebrity.” And while “The Apprentice” helped burnish Trump’s image as a tough-minded businessman and negotiator that has been crucial to his 2016 campaign, the pop culture projects that preceded it used Trump as everything from a sex symbol to an icon of wealth and the foremost representative of New York.
“Sex and the City” is hardly the only pop culture artifact to treat Trump like something of a sex symbol. In the Razzie-winning “Ghosts Can’t Do It,” from 1989, Trump is declared “Too pretty to be bad” when he tries to threaten a woman. And when he showed up on “The Nanny,” Fran Drescher flirts with him even as she’s introducing Trump to another man, only to stop short and say that she doesn’t have to make the connection because “All you handsome zillionaires know each other.” When Trump showed up on Denis Leary’s show “The Job,” he planted one on Elizabeth Hurley and teased Leary about whether they were dating. Trump’s hair and clothes may seem schlubby today, but at a certain point in the ’90s and the early 21st-first century, he had enough sex appeal that pop culture was eager to riff on it.
In a similar way, Trump has long been an instantly recognizable symbol of New York, in all its glitz and vulgarity; whether he’s appearing on screen or invoked in conversation, he has been a useful bit of Hollywood shorthand for decades.
When Kevin McCallister (Macaulay Culkin) gets on the wrong flight in the 1992 sequel “Home Alone 2: Lost In New York,” it’s Donald Trump who materializes to give the little boy directions in the Plaza Hotel. In the 1996 Wall Street comedy “The Associate,” Frank Peterson (Tim Daly) tries to use Trump’s name to get a table at a packed restaurant. “Sex and the City” name-checked Trump in the pilot and put him on screen in a second-season episode where Samantha spots him having a drink at a bar and declares herself to be having the quintessential New York afternoon. And he’s one of the many celebrities who show up to give testimonials to the transformational role Derek Zoolander (Ben Stiller) played in male modeling in “Zoolander.”
Woody Allen had Trump play himself in “Celebrity,” telling a camera crew that “I’m working on buying St. Patrick’s Cathedral, maybe doing a little rip-down job and putting up a very, very tall and beautiful building,” a joke both on Trump’s grandiose claims to transform iconic real estate and the way anything, even an internationally famous church, can change in New York. On the long, hot day chronicled by Spike Lee in his 1989 movie “Do the Right Thing,” there’s some discussion of whether Sal (Danny Aiello) should sell his neighborhood pizzeria and get in on the Trump-fueled real estate craze.
And Trump’s riches have long been a way of providing a sense of scale to fictional characters’ money and businesses. In one 1994 episode of “The Fresh Prince of Bel-Air,” “For Sale by Owner,” Trump’s appearance in the Banks family’s living room is enough to send Carlton (Alfonso Ribeiro) into a dead faint. The Bankses live a luxurious life, but in a sign of The Donald’s wealth, he ends up deciding not to purchase their home; it doesn’t meet his standards of luxuriousness. He brags about his business acumen in “Eddie,” a 1996 comedy where Whoopi Goldberg becomes the coach of the Knicks, flashes his influence on “Spin City” and gives Drew Carey a hard time about the fact that his ice cream truck doesn’t sell ice cream on “The Drew Carey Show.”
Even Trump’s divorce from Ivana Trump produced a sly pop culture moment. Ivana, who fought a fierce battle against her ex-husband when they split, showed up in the 1996 dramedy “The First Wives Club” to tell Diane Keaton, Goldie Hawn and Bette Midler — playing characters who, like Trump, had been abandoned for younger women — “Don’t get mad. Get everything!”
The Donald Trump who emerges in his film and television roles is less harsh than his presidential campaign has been, more attuned to audiences’ aspirations to wealth and power than to their fear that their lives have become increasingly precarious. The sheer length of Trump’s credits reel is a testament to his persistent appeal. His performance in the 2016 presidential campaign may be his most consequential role yet. But he — and Hollywood — has been selling himself to the American public for decades.