IN A 1997 EPISODE OF THE DREW CAREY SHOW, DREW, AN assistant personnel director at a Cleveland department store, drives to New York City with his friends to see a Yankees game, in the old ice cream truck they use to deliver beer from their home brewing business. They end up marooned in bumper-to-bumper midtown traffic, as an impatient Carol Channing rams them with her car.
While they stew in gridlock, a businessman hails them from the sidewalk: “Hot one, isn’t it? I’ll have a Nutty Buddy.” They tell him that they only have beer. “What are you, morons?” asks the man, whom Drew, his friends, and the home audience have all recognized by now as Donald Trump. After Drew explains the gang’s predicament, Trump reaches into a pocket and offers them his box seats. “Use them, enjoy them, and welcome to New York.”
By the 1990s, this was what Trump had become in pop culture: a walking, trash-talking, comical synecdoche for New York, its abrasiveness, and its sense of opportunity. He was a tourist sight, like the lights in Times Square, the window of Tiffany’s, or the giant electronic keyboard at FAO Schwarz.
Or the Plaza Hotel. In the 1992 movie Home Alone 2: Lost in New York, Kevin McCallister (Macaulay Culkin), separated from his family in the big city at Christmastime, wanders into the Plaza—all festive trim and crystal chandeliers and chamber music—and asks a grown-up in a topcoat where the lobby is. The joke is that Kevin doesn’t recognize the hotel’s owner, Donald Trump.
When Home Alone 2 came out in theaters, Trump was actually in the midst of being forced to unload the Plaza as part of a packaged bankruptcy agreement. But in the universe of the movie, it was still his. It wouldn’t really work, in a kids’ jingle-bell comedy, to have Middle America’s favorite lost tyke ask directions of a consortium of international lenders including the Industrial Bank of Japan. You need a person. You need someone to play the character. You need Donald Trump.
Not for the last time, Trump had found partners invested in his illusion, for whom the narrative of Donald Trump was too important to let the reality of Donald Trump ruin it.
THERE WAS AN almost impossible neatness to the timing of Trump’s business downfall at the beginning of the 1990s. It was as if the 1980s couldn’t end without taking Donald Trump with them—at least, the version who was the decade’s love-to-hate-him business protagonist. Wayne Barrett, who investigated Trump’s New York real-estate machinations at the Village Voice, saw a hint of the zeitgeist in Trump’s late-’80s buying spree, including the Plaza. “It was as if he looked ahead on a calendar,” Barrett wrote, “and decided that January 1, 1990, was the deadline: Anything he hadn’t bought by then could never be his.”
For years, he had made a string of debt-financed deals, his celebrity seducing lenders into offering easy money. Trump was “astonished,” Barrett wrote, “that he suddenly seemed to have the same impact in a Citibank boardroom that he’d once had on the Donahue show.” Then in 1990, those aggressive acquisitions—the casinos, the airline, the Plaza, not to mention “props for the show” like his yacht—smashed up against a recession. He ended up working out a plan with his creditor banks to restructure his loans.
But as the deal diminished the businessman Donald Trump, it made sure to preserve the celebrity Donald Trump. His role in his businesses was curtailed. But he was put on a $450,000-a-month budget, the reasoning being that he needed to keep up “appearances” in order to sell off assets at a decent price. Just as publicity made his successes seem greater than anyone’s in the 1980s—they had to be greater, they were on TV!—so would it make his losses seem bigger, more devastating, more humiliating, if the media fixture with the T-shaped gold cufflinks couldn’t keep up the show.
In a society where success was driven by image, a Donald Trump without his set dressing might as well be parading in public wearing a barrel. Like an actress in borrowed jewels at a red-carpet premiere, he had to present an appearance. Citibank needed him to keep playing his character the same way that Home Alone 2 did.
Also in 1992, Trump was divorcing Ivana, a tabloid blowup that managed to belittle and inflate him at the same time. It dominated the gossip columns the crackups of old Hollywood once did, like the febrile in-and-out-of-love story of Elizabeth Taylor and her fifth (and sixth) husband, Richard Burton. There was the love triangle: Trump, Ivana, and Marla Maples, an aspiring actress and one-time Miss Resaca Beach Poster Girl. There was a feeding frenzy, a rehearsal for the later 24/7 superstories—the Nancy Kerrigan/Tonya Harding fiasco at the 1994 Winter Olympics, the O. J. Simpson murder trial, the Monica Lewinsky scandal—that culture critic Frank Rich christened “mediathons.”
The real-life drama played like an episode of Dynasty, as when Ivana, according to People magazine, confronted Maples at a slopeside restaurant in Aspen: “You bitch, leave my husband alone.” Both Trumps leaked to gossip columnists—Cindy Adams, Liz Smith—and the New York tabs went into red-siren mode. (“Best Sex I’ve Ever Had,” the New York Post blared, a headline a Post reporter later said was fed to the paper by Trump himself.) The new TV entertainment magazines, with whose sensibility the straight news increasingly had to keep pace, amplified all of this. It was on ABC’s Primetime Live, to Diane Sawyer, that Maples publicly confessed her love for Donald.
There was already, in Trump’s 1980s media image, a counterimage of him as an absurdity, vain, loudmouthed, and tacky, a self-inflated gold-lamé balloon high on his own helium. The New York satire magazine Spy, founded by Kurt Andersen and Graydon Carter, was especially lacerating and precociously insightful. It coined the most memorable epithet for Trump—“short-fingered vulgarian,” the adjectival portion of which his 2016 Republican opponent Marco Rubio extended, as it were, to imply that he had a small penis. But beyond that, it pegged him as a bloviating fraud, a Potemkin businessman; it labeled him “Donald Trump, the demibillionaire casino operator and adulterer” and mocked his pretensions of weighing in on world issues.
Now all of America could see Donald Trump as Spy did. The Maples publicity, on the one hand, made him a bigger name than ever. Even as Trump decried the “very dishonest” press coverage, he fed and abetted it. He could no more resist it than a flower can will itself not to turn toward the sun. But it also made him into a joke—the guy who used to be Donald Trump.
BETWEEN THE BREAKUP OF his marriage and the breakdown of his businesses, 1990 tends to be considered the nadir in Trump’s career. It was, if you believe, incorrectly, that he was primarily a businessman.
But if you believe that he was primarily a celebrity who leveraged his fame into business, then the 1990s were a defining period of his career—maybe more so than the 1980s. In the 1980s, Donald Trump was a businessman who used celebrity as a helpful promotional device. By the 1990s, he was a celebrity whose calling card was the ability to play the figure of a businessman. He would leverage that performance—the self as a character, wearing the Halloween costume of a mogul—to make himself a reality-TV star in the 2000s and a politician in the 2010s.
And the 1990s were when playing “Donald Trump” became his full-time job.
You can understand the Trump of this period with the help of another former big ’80s sensation: postmodern theory. The postmodernists (among them Baudrillard, Fredric Jameson, and Jean-François Lyotard) were concerned with the “simulacrum”: the copy or representation of a thing, which, in a culture dominated by reproduced and faux images, comes to supersede the original. “The image can no longer imagine the real,” Baudrillard wrote, “because it is the real.” Actual nature, seen in person, disappoints next to impeccably shot nature documentaries. The 1950s of American Graffiti replace the actual memory of the 1950s. The Piazza San Marco in the Venetian Hotel in Las Vegas—just a stroll away from reproductions of New York City, Rome, and ancient Egypt—supersedes the one in Venice.
And Donald Trump the simulacrum, the performance, had in Baudrillardian fashion eclipsed Donald Trump the businessman—so much so that the former would have to bail out the latter.
Trump had created a business whose primary product was the idea of Trump: swagger, glitter, hitting it big. Separated from that brand, his troubled properties would be worth less than they already were. In the 1990s, that name became the business. Increasingly his business ventures were like the Trump International Hotel & Tower, where he worked with deep-pocketed partners and contributed his famous brand. (Upon its opening, the New York Times described it: “It’s Donald J. Trump. All 52 stories of him.”)
His job became essentially to play, on and off television, the role of Donald Trump, mascot.
THE CORPORATE MASCOT is one of the great American literary devices. A business invents a character to embody its image. That character has attributes, themes, even backstory and narrative. Like a comic-book superhero or a mythological figure, it personifies abstract ideals. In 1877, the Quaker Oats Company registered a trademark for “a man in Quaker garb” to symbolize “good quality and honest value.” In 1890, a grain-milling company hired a former slave to play the role of Aunt Jemima—a racist caricature drawn from minstrel shows—to associate its labor-saving product with a smiling, subservient domestic worker.
Occasionally, a real person could be apotheosized into an immortal branding symbol. In 1964, when Colonel Harland Sanders sold his company, Kentucky Fried Chicken, it was with an agreement that transformed him, via TV commercials and takeout buckets, from a mere man—ambitious, demanding, with a penchant for cursing out his employees—into the personification of flavor, down-home quality, and Southern graciousness. According to a New Yorker profile, the new owner, John Y. Brown, saw that the Colonel’s goatee and white suits were as valuable as any secret recipe:
the possession of a symbol who was both authentic and alive—unlike Betty Crocker, Colonel Morton, or Aunt Jemima, for instance—was one of the company’s greatest assets. He hired a public-relations man in New York, and the Colonel soon was popping up on the Tonight Show, The Merv Griffin Show, and other network programs, where he more than held his own with the show-business pros.
Colonel Sanders’s human body died in 1980, the year the Donald Trump TV character materialized on Tom Brokaw’s couch. But “the Colonel,” the character Sanders played, long outlived him—stylized, ironized, polymorphous, and pangender, played in commercials by comedian Darrell Hammond and country singer Reba McEntire. Like Jesus represented by the cross or a fish, he was essentialized in a few potent gestures: a goatee, a string tie. He was even repurposed in literature, appearing as a semimagical, sentient “abstract concept” in the novel Kafka on the Shore by Haruki Murakami.
Likewise, Donald Trump discovered that the abstract concept of him had a life of its own, and a potentially more successful career. He too, like the Colonel, was encapsulated in a few visual signatures: a solid-colored tie, a purse-lipped sneer, the male-model stare, and that hair. That impossible, Suessian tuft of hair, whatever wizardry of science and man made it possible, was like a crown that he snatched from the Pope and placed on his head, Napoleon-style. Watching his appearance evolve over the decade, become more exaggerated and stylized, is like watching a corporate logo change through successive redesigns, starting with something crude and literal—a telephone, a globe—and over the years become simpler and more glyph-like, not the thing, but, better, the abstraction of the thing, the thing that the thing makes you feel.
You have to wonder if business success was less important to Trump than becoming one of the immortal American brands, which are our undying gods, embodying aspects of the national character. Coca-Cola: a little caramel color, a little sugar, and the ideas of youth and vitality. Chevrolet: tail fins, polish, and faith in the endless possibility of the American road. Trump: a brass nameplate, aggression, and the belief that your appetites are good and correct.
THE 1990S WERE a boom time for the businessperson as personal brand—moguls like Martha Stewart and Oprah Winfrey, whose personalities and biographies were bound up with their products. Trump, whatever his status as an actual businessman, was valuable as the easily recognizable cartoon of “a businessman.” And right around the time his actual business ran into trouble, he began assembling a list of movie and TV appearances—to use the language of credits listings—“as himself.”
In 1991 he won the Golden Raspberry Award as “Worst Supporting Actor” in the film Ghosts Can’t Do It, playing opposite Bo Derek, the sex-symbol star of 10, in a goofily seductive business negotiation. (“You’re too pretty to be bad,” she purrs. He pouts his lips: “You noticed.”)
In a 1994 episode of The Fresh Prince of Bel-Air, a sitcom about a wealthy family who takes in their street-smart nephew from Philadelphia (the Diff’rent Strokes setup, except the benefactors are also black), he shows up with Marla Maples and a suitcase full of cash, interested in buying the family’s mansion. Carlton (Alfonso Ribeiro), the family’s enthusiastic preppy son, faints from excitement.
Even though he always plays himself, rather than a character—or rather, plays himself as a character, which he has done for his whole public life—Trump is a stiff actor. His lines sound like he’s reading more than speaking them. He’s not capable of forgetting in any moment that he is himself, a man standing on a soundstage and waiting for applause. But his woodenness underscores the meta-effect of his cameo appearance. You’re not meant to think, “Here are the characters on my favorite show talking to Donald Trump,” but rather, “Here are the actors on the set of my favorite show meeting the famous person Donald Trump.” (This effect is doubled when the Fresh Prince studio audience cheers when Trump shows up; they’re cheering, after all, for the “character” that they know from outside the story.)
On Spin City—the city-hall comedy starring Michael J. Fox, the 1980s’ Alex P. Keaton—Trump appears as himself to plug his book Trump: The Art of the Comeback. On The Nanny, the title character introduces Trump to her wealthy employer: “Who am I kidding? All you wealthy zillionaires know each other.” He flirts with model-actress Elizabeth Hurley on The Job; he plays poker on Suddenly Susan and jokes about a character’s divorce; on HBO’s Sex and the City, he’s eyeballed over cocktails by high-powered, high-libido publicist Samantha Jones. “Samantha, a cosmopolitan, and Donald Trump,” says Sarah Jessica Parker’s voiceover. “You just don’t get more New York than that!”
In actual, brick-and-mortar New York, Donald Trump was known to readers of the tabloids as a has-been. But in the virtual landscape of TV and the movies, he was New York personified. He played the same character: a dashing, bemused man in a business suit or black tie, spending money, dispensing advice, insults, and baksheesh, creating a stir, turning heads, coming across less impressed with the characters he met than they were with him.
This had value to him, since maintaining his appearance and thus his brand was essential to keeping up the price of his assets. In the sitcom business at the time, a Fresh Prince director recalled, Trump “was one of those guys you would go after [for a cameo] because he was one of the few who would actually do it.” In fact, filmmakers said that casting him was often a precondition of shooting on one of his properties, which was often the reason they would approach him.
The productions secured a visual shorthand for wealth and success. Trump was like a skyline establishing shot. You open a film set in New York City with footage of the Empire State Building rather than, say, Frank Gehry’s 8 Spruce Street, because it immediately proclaims “Manhattan.” Likewise, even if you could cast a New York mogul more successful than Donald Trump in the 1990s (Carl Icahn, say, or Henry Kravis), you’d have to explain to your audience who it was.
Trump came pre-explained, pre-stereotyped, pre-cartoonified. He was his own Colonel Sanders, a logo that told you, at a glance, what flavor to expect. When he made a TV commercial for the Big N’ Tasty burger with McDonald’s jiggly purple mascot Grimace, he was collaborating with a peer.
LIKE A CHARACTER being retooled for a TV spinoff or a movie reboot, this “Donald Trump” was pitched differently than before. His character became comic-nostalgic, an unfrozen caveman Master of the Universe, walking through the world in a personal 1987 time warp, in his power suit and silk tie, in a world where young people now favored flannel and Doc Martens boots.
The 1990s were born in a recession and a screeching 180-degree turn toward suspicion of money and glitz. In 1989, Time had put Trump on the cover holding an ace of diamonds: “Flaunting it is the game, and TRUMP is the name.” By 1991, its cover featured a bicycle and a pair of beat-up work boots, hailing “The Simple Life.” (“These are the humble makings of a revolution in progress: Macaroni and cheese. Timex watches. Volunteer work. Insulated underwear. Savings accounts.”) The signature doorstop novel of the 1980s was Tom Wolfe’s The Bonfire of the Vanities, a social-realist tale of power and class conflict in a Manhattan dominated by alpha businessmen. Its 1990s equivalent—in ambition and tonnage if not in spirit—was David Foster Wallace’s Infinite Jest (1996), a comic-surrealistic excoriation of commercial media and consumer culture that imagined “the Entertainment,” a film so entrancing it killed its viewers, and that was set in a future in which years themselves were renamed for corporate sponsors. (Much of the novel takes place in “The Year of the Depend Adult Undergarment.”)
You could argue that the pop-culture ’80s ended in mid-1989, with Spike Lee’s Do the Right Thing. The film, which climaxes in a riot in Brooklyn, repudiated the idea that dollar-driven real-estate development was an unalloyed good for New York. (One memorable scene in the movie involves a run-in between a white gentrifier and the black residents of the neighborhood.) It also answered the kind of race-baiting that Trump had dabbled in during the 1980s. In 1984, a white subway passenger, Bernhard Goetz, shot four black teenagers that he said had been harassing him; news reports called him “the subway vigilante” but many white New Yorkers hailed him as a hero. White fear was the kind of atavistic force that Trump was wired to pick up on; his self-promotion in the 1980s drew on his image of himself as a savior taming the fallen “inner city.” On May 1, 1989, Trump took out full-page ads in four New York newspapers calling for the death penalty for “the Central Park Five,” a group of black and Latino teenagers (later exonerated) accused of brutally raping a jogger in Central Park. (In 1990, Trump called the youths “one step removed from animals.”) A few weeks later, Lee’s film—fueled by a decade of racial incidents and depictions of black youth as predators—premiered at Cannes.
In 1991, Richard Linklater’s film Slacker created a counter-archetype to the preppies and yuppies of the 1980s: aimless, eccentric young people seeking purpose outside a paycheck. It was the era of indie film and indie record labels, alternative this and alternative that—a bad brand environment for anyone who preferred to position himself as the default.
At the same time, TV’s class dynamics were changing in the 1990s, with both working-class protagonists and fantasies of wealth like Dallas and Dynasty being pushed out at either end. An advertising structure that rewarded shows whose audiences were young, white-collar, and middle class—what saved Hill Street Blues in the 1980s—now increasingly produced TV characters that fit that profile.
NBC’s “Must-See TV” programming bloc thrived on this sort of show. Seinfeld’s characters rarely seemed to work (except comically, as with George Costanza’s elaborate plots to get hired and fired from jobs), yet had time and cash to hang out at restaurants. Friends was as well known for its ludicrously oversized Manhattan apartments as for its romantic-comedy escapades. TV turned New York from a place of struggle and aspiration—if you can make it there, you’ll make it anywhere—to a pacified hangout of comfy couches and cappuccino.
With occasional exceptions like Roseanne, blue-collar work disappeared from television. The work that audiences did see, in the bourgie-fied TV of the ’90s, was increasingly white-collar. CBS, once the home of Norman Lear’s working-class comedies, refocused on shows like Murphy Brown, about a high-strung, high-powered TV-newsmagazine journalist who, after a day of butting heads with the powers that be, came home to a lush Georgetown townhouse.
It wasn’t only working-class people (and partly by extension, minority characters) who were dwindling in prime time. The super-rich were too. The flip side of television becoming more bourgeois was that the kind of outlandishly wealthy characters popular in the 1970s and 1980s were passé. Even Aaron Spelling’s teen soap Beverly Hills, 90210, though it was set in the toniest Southern California zip code, saw the land of plastic surgery and privilege through the lens of Brandon and Brenda Walsh, a pair of upper-middle-class transplants from Minnesota.
That soaps about the rich would dwindle at the same time TV about the working class did might seem like a contradiction. But it’s really part of the same phenomenon. You didn’t program a show like Dynasty to attract the Carringtons of the world. Like celebrity magazines in the checkout line, they’re a populist medium. The sybaritism of the wealthy is escapism for people just getting by, who like their rich people as decadent and gold-trimmed as Donald Trump’s triplex. Soaps of the 1980s were the class struggle dialed up to 10 and played to the groundlings.
But the kinds of viewers that networks increasingly prized by the 1990s—college-educated, with good, steady incomes—weren’t as drawn to that kind of fantasy. For them, life wasn’t all-or-nothing; it was something, and something a little more tomorrow. (Trump’s 2016 campaign would, in part, appeal to resentment of “elites”—not the actual super-rich elite, but the comfortable white-collar class, the lawyers and managers who maxed out their 401(k)s and test-prepped their kids into selective colleges and made their money off intangible thought work, money for nothing. If Trump had a life you wanted though you knew you could never have it, these professionals had a life you needed accreditation to even know how to want.)
These viewers gravitated to network-TV characters who were, socially, more like themselves: the journalists on Sports Night, the lawyers on Ally McBeal. They liked the dry irony of David Letterman. They responded to The Larry Sanders Show’s depiction of the Hollywood entertainment machine as powered by cynicism, and Twin Peaks’ vision of a cherry-pie rural American town riddled with demons, addiction, and child prostitution. They liked referential humor and series that rewarded the sort of ability to read symbol and subtext that earned you As in a literature class. You made shows like Frasier—the Cheers sequel about a wine-sipping, bon mot–dropping psychiatrist and radio host—because you wanted viewers like Frasier.
BY THE EARLY 1990S, America had become partial to a different brand of real-life rich person. The 1992 presidential election, one cycle after Trump teased the possibility of running on Oprah and Donahue, saw the independent campaign of H. Ross Perot, a Texas data-systems billionaire with a ’60s-NASA-engineer buzz cut and the voice and bearing of a rooster that a wizard had turned into a man.
Perot, who won nearly 20 percent of the vote, was the evolution of the Trump-Iacocca idea—amplified by Republicans in particular for years—that America should be run like a business. Like Trump in 2016, he was a novelty who bathed in free publicity. He essentially began his campaign by coyly telling Larry King, CNN’s suspender-wearing old-Hollywood schmoozer, that if “everyday folks” put him on the ballot in all fifty states, he’d make the sacrifice of running.
He chirped out folksy catchphrases; the NAFTA trade deal, he said, would produce a “giant sucking sound” of jobs moving to Mexico. He relied on his mastery of live TV, especially the debates. He de-emphasized traditional TV ads, buying half-hour blocks to give economic lectures with cardboard charts, which out-rated prime-time sitcoms. (There was not, yet, an ecosystem of competing cable-news channels to give his insta-celebritized campaign events hours of free airtime.)
Perot was proto–reality TV, at a time when reality TV barely existed outside MTV’s The Real World. He had an anti-slick performative populism, bolstered by his claim to simply be doing the bidding of average Americans. (His ballot challenge on Larry King was an early version of the viewer-participation model of American Idol: only you, America, can decide whether he returns on the show next week!) And he was an early test of the idea that a billionaire could argue that he was closer in spirit to paycheck-to-paycheck Americans than the professional classes that, in dollar terms, stood between them.
Perot was not exactly the Trump model of business mogul. His style was more Timex than Rolex. His celebrity was anti-celebrity; he commanded television by being anti-telegenic. In Dallas, the Los Angeles Times reported, “Locals say they see him shopping at the local sporting goods store or driving to his Saturday haircut in an ’87 Oldsmobile.” Donald Trump cultivated an affect that said to an observer, at a glance: “Wealthy business magnate.” Perot’s exterior said: “Refrigerator salesman, maybe?”
In business culture, meanwhile, the momentum was shifting away from swaggery ’80s personalities like CNN’s founder, Ted Turner, the mouthy Georgian who married actress Jane Fonda and competed in yacht races. The countenance of wealth was changing, in part, because the sources of wealth were changing. The face of money in the 1990s was technology wealth: America Online’s Steve Case, Oracle’s Larry Ellison, Amazon’s Jeff Bezos, Yahoo!’s Jerry Yang, and Microsoft’s Bill Gates.
There was already a template of American wealth, within which Donald Trump had situated himself: rich people made and sold concrete things you could see and touch. They built cars, extracted oil, launched airplanes, built buildings. (There was an implicit idea of masculinity and virility in the physicality of their achievements: you erect a skyscraper.) Technology wealth, on the other hand, was wealth from intangibles. Cornelius Vanderbilt, in the nineteenth century, made his fortune in railroads—vast physical networks than veined a continent, through which its physical riches pulsed. Networking software, on the other hand, is not a railroad but a metaphor for a railroad. Yahoo! was a place on the Internet that helped you get to other places on the Internet. Getting rich from an operating system is like getting rich by selling air.
Tech moguls built ideas. They certainly would not do anything so déclassé as to slap their name on a giant tower, like some sort of caveman.
You could understand the value of a car by going to your garage and starting it up. The tech empires created wealth out of things that required abstract thinking before you could even understand that they were things. (What is a “site” on the Internet, anyway?) There was also computer hardware, sure, but a beige work tool doesn’t scream “luxury” like a gilded tower. Even Amazon—the virtual bookstore turned superstore whose raison d’être was to make “brick and mortar” an archaism—didn’t make things at first but rather the means to buy things. Money for nothing!
The new money of the 1990s also redefined the aesthetic of wealth. The uniform of the tech-rich was the jeans and open-necked shirts of the engineers and programmers they often started out as. Theirs was the ostentation of anti-ostentation. Bill Gates, with the fortune of a Gilded Age monopolist and a fearsome business reputation to match, wore V-neck sweaters and oversized glasses like some sort of harmless Muppet.
It was, to borrow the name of a 1996 PBS documentary by Robert X. Cringely, the Triumph of the Nerds. (Cringely—the pen name of journalist Mark Stephens—was, in his own description, the “premier gossip columnist” of the computer business, a Liz Smith for introverts.) As Cringely describes his tech-leader subjects in Triumph of the Nerds, they “were, for the most part, middle-class white kids from good suburban homes,” and they displayed their power and independence by continuing to dress like suburban kids.
This economic shift blossomed into a cultural one—not least because technology was an expression of culture. The 1990s was a boom time for nerdery: nerd music, nerd pastimes, nerd icons like Steve Urkel of the sitcom Family Matters. To be a nerd was to oppose the signifiers of a red-blooded tradition, as Benjamin Nugent writes in American Nerd, in which “the heroes of American popular culture are surfers, cowboys, pioneers, gangsters, cheerleaders, and baseball players, people at home in the heat of physical exertion.” Nerd exertion was mental. Nerd empires were intangible. Nerd aggression was passive-aggression. And nerd consumption was inconspicuous.
There was one member of the nerdocracy who had a significant aesthetic, and it was a repudiation of 1980s polished-brass glitz. Steve Jobs of Apple would become far wealthier than Trump, but he cultivated a stylistic asceticism: black turtleneck, wire-rimmed glasses. He insisted that Apple’s products be beautiful. (He originally wanted his computers to come in blond koa-wood cases.) And he defined beauty by absence: clean lines, no filigree. This eventually led to the iPhone, whose glass touchscreen was as close to a blank portal to pure idea as modern hardware could create.
Jobs was selling consumers an idea of themselves as much as he was selling machinery. Apple’s computers (and later phones and tablets) were high-design status objects. They sold at a premium. But they communicated status austerely, by rejecting ornament. Jobs popularized a kind of anti-materialist materialism. It was no longer “If you got it, flaunt it.” By refusing to flaunt it, you proved you were someone who got it.
WELL, WHAT THE HELL does Donald Trump do in this world? He had managed, through his face-saving deal with his creditors, to hang on to the props of success and wealth. But being Donald Trump was never entirely about the money. It was about leaving his stamp—his golden T—on his age. The Donald Trump of 1987 was America’s gluttony artist. A decade later, he was what? A rich landlord. A regional celebrity. A museum piece with no more grip on the popular imagination than a railroad tycoon.
Trump had been eclipsed and outbillionaired by tech and media entrepreneurs who captured the popular imagination the 1990s way, by buying and selling pieces of it. Mere solvency is small comfort to a man who—a securities analyst familiar with him told The New Yorker—“wants to be Madonna.”
But media and entertainment still needed a symbol of flashy, richly marbled wealth that anyone could understand in a second. They still required a cartoon zillionaire who would preen and shake his moneybags the way Silicon Valley’s abstemious captains didn’t. The character of Donald Trump was out of fashion, but he usefully filled a niche. In a culture of minimalists, he was a maximalist. If in the 1980s he was the programming, in the 1990s he was the counterprogramming.
He was ubiquitous, for instance, in ’90s hip-hop lyrics, in which “Donald Trump” was a three-syllable anapest for in-your-face riches. “Put more cash in my pockets than Donald Trump” (Master P); “Guess who’s the black Trump?” (Raekwon); “I’m just tryin’ to get rich like Trump” (Ice Cube); “In hot pursuit of Donald Trump rap loot” (Pete Rock); “I need a suite with the flowers complimentary at Trump Towers” (Nas, who’s referenced Trump in lyrics at least eight times). By the 2016 election, after his calumnies against the first black president, hip-hop would turn overwhelmingly negative on Trump, but in the ’90s, he was mostly a useful verbal ornament, a kind of human gold chain.
The man who, in the 1980s, festooned himself with luxurious “props for the show” became himself a kind of prop, a useful gimmick to cast in TV commercials and promotions. During CBS’s coverage of the 1994 Winter Olympics, he introduces coverage of moguls, before being told that “moguls” here means the skiing event. For Toshiba desktop computers, he answers an email from a twelve-year-old boy who writes him for advice on becoming a real-estate tycoon. In a Pizza Hut ad, he and his ex-wife Ivana tryst in a swanky apartment and agree to do something that she says is “wrong” but he says “feels so right”: eat the new Stuffed Crust Pizza crust-end first.
If people never really change, the useful thing about fictional character franchises is that they can, adapting to the tone of the times while maintaining the core identities their creators laid down. Batman began as a stone-faced gangster fighter; then he was a campy kids’-show favorite, played by Adam West in sausage-skin tights; then he was a brooding vigilante in dark, violent films. But the essentials remained the same: lair, gadgets, justice.
The 1990s were Trump’s Adam West period. His appearances “as himself” carried the seed of his aspirations and self-image, encased in a protective gel of irony, to survive until a more hospitable time.
THIS USE OF IRONY as an impermeable defensive carapace was a particular concern of novelist David Foster Wallace. In 1993, he published an essay, “E Unibus Pluram: Television and U.S. Fiction,” which sketched out some of the ideas about media that he would expand on in Infinite Jest. Television was not just dominating Americans’ attention, Wallace wrote, but it had developed an amoeba-like ability to enfold and absorb any critique by archly laughing at itself from a posture of “hip irony.” You could see this in the amount of TV that was reflexively about TV (the news-business comedy Murphy Brown, or the meta-referential detective show Moonlighting, or Beavis and Butt-Head, the MTV cartoon whose characters made fun of MTV videos) or that spoofed its characters’ own fixation with TV (Homer Simpson spacing out staring at the tube as you spaced out staring at Homer Simpson). First TV comedy parodied commercials, as on Saturday Night Live, then commercials parodied commercials, like the Isuzu ads with the sleazy pitchman Joe Isuzu, which sold cars by telling you how much you hated people who sold cars.
Against this, literary fiction seemed outmoded, overmatched, like it was fighting off space aliens while armed with nothing but pointy sticks. Do you approach television in fiction writing mimetically, treating TV and its language as another aspect of contemporary realism, and thus affirm it as a fixture of the landscape? Or do you try to rebel against it, and risk becoming another preachy square who just doesn’t get it? Either you surrender or you are impaled on your own lance. “Televisual culture has somehow evolved to a point where it seems invulnerable to any such transfiguring assault,” Wallace wrote.
It’s important to keep in mind that David Foster Wallace liked TV. He was just over thirty when “E Unibus Pluram” came out. He was no tweedy, “I don’t even own a television” fogey. He belonged to the generation after Trump’s, who first knew television not as a novelty but a fact of mundane existence. Unlike many intellectuals—and to be honest, TV critics—of his time, he didn’t regard TV shows as dangerous objects to be held with tongs at arm’s length, or folk artifacts with which to anthropologically study the great unwashed. He writes with the familiarity of a dedicated viewer. “I know I watch for fun, most of the time, and that at least 51 percent of the time I do have fun when I watch,” he wrote.
But Wallace appreciated TV enough to take it seriously, and he was conscious of the ways it worked on him. Addiction—chemical and psychological—was a preoccupation of his, and he wrote with conviction on how the medium’s effortless stimulation appealed to “teleholics.” He also noticed TV encouraging a kind of lazy superiority in its viewer. “It’s just fun to laugh cynically at television—at the way the laughter from sitcoms’ ‘live studio audience’ is always suspiciously constant in pitch and duration,” he noted. With that default to mockery came the danger of learning to see everything as fraud and artifice, deciding that everyone was phony, and thus being willing to excuse those phonies who admitted it with a wink. (As another old artificer, P. T. Barnum, put it more than a century earlier: “The greatest humbug of all is the man who believes—or pretends to believe—that everything and everybody are humbugs.”)
In Wallace’s view, some of the greatest carriers of this kidding-not-kidding sickness were the late-night talk shows: “[David] Letterman, Arsenio [Hall], and [Jay] Leno’s battery of hip, sardonic, this-is-just-TV shticks.” Letterman, for Wallace, was the Typhoid Mary of death by irony. Letterman’s show, the outgrowth of a brief, surrealistic morning show he attempted on NBC in summer 1980 (it followed Trump’s appearance on Brokaw’s Today), was a kind of mad scientist’s sentient monster, a talk show that knew it was a talk show. The show’s mascot was Larry “Bud” Melman (Calvert DeForest), a doughy, leering martinet who was like an emcee from a twisted David Lynch dream. The bandleader, Paul Shaffer, affected a knowingly corny lounge-lizard persona. Letterman would mock and prank his own network, showing up on the set of Today with a bullhorn, crying, “I am Larry Grossman, president of NBC News, and I’m not wearing pants!” Wallace’s short story “My Appearance” is a minutely observed rendering of a TV actress’s guest spot on a 1989 episode of Late Night with David Letterman, which both perfectly captures the show’s voice and depicts it as a kind of secret-in-the-open horror show, the absurdist gags and wisecracks masking a psychological assault of contempt and misogyny. The actress’s husband, who works in the entertainment business, prepares her for the taping, warning her: “Meanness is not the issue. The issue is ridiculousness. The bastard feeds off ridiculousness like some enormous Howdy-Doodyesque parasite.”
This criticism of Letterman, I think, is broadly accurate but not entirely right. His irony and sarcasm could be a crutch, but they weren’t just nihilism. They expressed a genuine disgust for phony bonhomie and artifice, something that became clearer over the years as he aged and changed his style, becoming less of a prankster, more of a raconteur, and more straightforwardly outspoken. (It was Letterman, in 2011, who was one of the first to take Trump seriously enough to call him a racist, in so many words, for pushing the smear that Barack Obama was not born in the United States, even as serious news outlets indulged Trump as a harmless buffoon: “It’s all fun. It’s all a circus. It’s all a rodeo. Until it starts to smack of racism.”)
But of course it also says something that Letterman did change his style, that he found it necessary to find a voice in which he could argue what he believed to be true and not simply what he derided as fake. And the environment of his 1980s and 1990s talk shows, on NBC and later CBS, was inarguably helpful to a certain kind of guest who wanted to enter that everything’s-a-joke zone to launder his own reputation.
DONALD TRUMP APPEARED on Letterman’s shows more than thirty times, over three decades. These appearances were valuable exposure, but along with his other talk-show visits, they also established a dichotomy—that Trump was both businessman and entertainer—that would be essential to him as a candidate. When you are always in a Schrödinger’s-cat paradox of joking and not joking, the same message can send different meanings to different audiences: I mean it but I don’t really mean it but I do. (Wink.)
On talk shows like Letterman’s, Trump played a shock comic. Letterman delighted in prodding Trump to shoot his mouth off but also pressed him on his controversies. In a 1992 appearance, summing up how he’d sold off his assets as he faced potential ruin, Trump said, “I sold the Trump Shuttle. I unloaded my wife.” The audience howled. Later, Letterman asked him about a proposal Trump had made, that prizefighter Mike Tyson should be allowed to reduce his prison sentence for rape by fighting a charity bout. “What were you thinking?” Letterman asked. “I was thinking as soon as he gets out, he’s going to box at my casinos.” Awkward silence. “I was only kidding when I say that, folks,” Trump added.
There’s a preview in this appearance of Trump the political figure, and not just because Letterman asked him to handicap Ross Perot’s odds in the coming election. There’s the joking-not-joking dance: I’m telling it like it is, but also I didn’t really mean it—but also I’m more honest than all the phonies, because I’m just saying what everybody’s thinking. (That too is an entertainer’s defense, from Andrew Dice Clay to Eminem.) And you—you smart people—you’re in on the joke. You get it.*
It also shows Trump participating in that most essential of celebrity-culture rituals: the comeback story. There are three elemental celebrity stories: you rise, you fall, you bounce back. For a traditional businessman, Donald Trump’s 1990 might have been irreparably humiliating. But for a celebrity—Robert Downey Jr., Drew Barrymore, Rob Lowe—it’s a valuable item on a résumé.
On Letterman, Shaffer and the World’s Most Dangerous Band played Trump on to the theme from Rocky (maybe ironically, maybe half-; Rocky Balboa didn’t win until Rocky II). Trump, like an ingenue with savvy handlers, wanted to begin the “comeback” part of his story as soon as possible. He would work that angle for much of the decade, publishing The Art of the Comeback in 1997. Presented as a business book on the model of The Art of the Deal, including a desultory list of “comeback tips” (including “be passionate” and “stay focused”), it was really a celebrity memoir at heart. The name-dropping reeked of sad ’80s reverie—Michael Jackson, Madonna, Carl Icahn—and the book was plastered with more celebrity photos than a Planet Hollywood franchise. (How dare you call me a has-been! Look at me here with Sly Stallone!)
Neal Gabler writes in Life the Movie that the celebrity-comeback story follows the arc of Joseph Campbell’s “hero with a thousand faces.” An extraordinary person surmounts extraordinary forces and returns to share rewards with his fellow man. Just so, “the celebrity loses it all, a victim of his own hubris or of the public’s fickleness. Only then, after he has been forced to win back his fame, does the celebrity reemerge from Hollywood, if only figuratively, in magazines and books and television talk shows, sadder but wiser, to tell the rest of us what he has learned.”
The Art of the Comeback’s story is not really a business story. It’s a Hollywood story—a retelling of the American myth of how the secular god, the celebrity, dies and is resurrected. I got big, the story goes. I got too big. I took my eye off the ball. I crashed. I fought back. And I learned an important lesson: “I enjoy my successes much more because I realize it wasn’t so easy after all.” I’d been to Paradise, and now I’ve been to me. Trump would use that precise story as his scripted introduction, in 2004, for The Apprentice.
Trump’s Art of the Comeback tour hit the same sorts of venues— TV newsmagazines, morning shows—as a Hollywood star peddling a tale of addiction and recovery. But it would leave out some typical themes of the celebrity-comeback story: humility and forgiveness. When Matt Lauer on the Today show asked him about his belief in getting revenge on people who wronged him during tough times—“Why not be bigger?”—he answered, “I like being small.”
Celebrity comeback stories are modern-day religious parables. Showing how the lofty overcame struggles and let go of their resentments, they offer the reader or viewer a kind of New Testament–New Age inspiration—I will make it through my own troubles, I will let go the anger and resentment, and I will emerge a better and happier person.
Trump’s self-authored comeback story used the same structure, but arrived at a much more Old Testament, even premoral lesson, that your bitterest fantasies are the ones you should nurture, indulge, and carry forward in life.
Someday things are going to swing back my way, and everyone who laughed at me is going to be fucking sorry.
* That side of Trump would turn up more often later in the decade, when he became a regular on shock jock Howard Stern’s show, rating female celebrities’ bodies (“A person who is flat-chested is very hard to be a 10”) and promising to change the Miss USA pageant, which he acquired in 1997, by getting “the bathing suits to be smaller and the heels to be higher.”