The ascension of Donald Trump to President of the United States is a triumph of stupidity, hatred, fear and reckless nihilism. The not-new cynical alchemy that used economic despair to stoke a widespread persecution complex with misidentified perpetrators, producing votes and a sham “movement,” seemed to rapidly accelerate a national death wish that was until now only bubbling latently under the surface. The country will probably make it to 2020, but Trump’s normalization and coronation augur a manifestation of dark suicidal energies that won’t soon slow. In the past few months of presidential transition, Trump’s nightmarish cabinet picks and the live-tweeting of his own slip into deeper dementia have put to bed any lingering reasons to feel in any way optimistic about his term.

There are numerous ways to approach the question of How We Got Here, but the one most relevant to this magazine’s film section is how entertainment so wholly trumped reality. The shape-shifting, inhuman production that is “Donald Trump” was a joint creation of the media and himself. In the 1980s, New York tabloids did the legwork, laying the foundation of the myth of a playboy businessman who personified rich and successful New York. No matter that his successes were relatively minor and his failures numerous—he was an easy go-to for deadline-wary writers needing an easy byword. Trump was happy to oblige, realizing that, in Neal Gabler’s words, “in order to compete with entertainment, one had to turn oneself into entertainment.” He went so far as to call reporters masquerading as a “John Miller” or “John Barron,” touting Trump’s supposed romantic conquests to the tabloids, displaying his gift for the one talent at which he’s most adept: brand maintenance. With this (charmless, stupid) persona fully formed by the end of the 80s, Trump could spend the rest of his life merely perpetuating its currency, with startlingly few tweaks. An efficient method was to trot it out on television and in films, in which he could appear as “Donald Trump” or his few other credited “roles” as VIP Patron, Rich Dad, Forbes Cover Billionaire, etc., which has served lazy screenwriters needing a quick comic symbol as it did and does their tabloid predecessors.

Trump’s television credits, capped by his starring run on reality business show The Apprentice but also including beauty pageants, pro wrestling, fast food ads, sitcom cameos and a Comedy Central roast, number in the hundreds, but it’s illuminating enough to look at his dozen-odd feature film appearances as a window into his horseshit myth-maintaining abetted by the entertainment-industrial complex. Trump’s deep humorlessness, lack of acting ability and bottomless vanity are all there in his first film appearance as “Donald Trump,” in Ghosts Can’t Do It, from 1989, the same year that saw Trump: The Game released to toy stores. It was helmed by lightweight actor-turned-director John Derek—like Donald, a fan of trading in wives for much younger models like Ghosts lead Bo Derek. The “it” of the title is sex, and acting legend Anthony Quinn (possibly drunk as he laughs through his performance) plays the dead husband of Bo, who communicates with her from beyond, urging her to kill a young man who will serve as his corporeal surrogate. At one point, Bo’s character sits down for a business meeting with Trump, in which he warns her 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,” a line delivered with such lack of charisma that even he must’ve noticed, since he would rarely deliver one so long. When she tells him, “You’re too pretty to be bad,” he puckers at the camera and quips, “You noticed.”

Trump’s next two film appearances centered on his well-known ownership of Manhattan’s storied Plaza Hotel, dating from 1988 until 1992, the bankruptcy of which must’ve been particularly painful to him, hyper-aware as he was of its cache and standing in the city and compared to his tawdrier Jersey casino holdings. For their cash-in sequel to Home Alone, Chris Columbus and John Hughes plunked Mac Culkin’s Kevin McCallister down in still-scary New York City, somehow managing to spirit robbers Joe Pesci and Daniel Stern there, too, so as to recreate the violent slapstick. Kevin’s bizarre befriending of the homeless “Pigeon Lady” is juxtaposed with his brush with glitz, as embodied in the shorthand that would typify all cameos by Trump, who gives Kevin directions to the Plaza lobby (and a badly mugged bewildered head tilt). In The Pickle (1993), a conceptual misfire and box office failure that would be Paul Mazursky’s last opportunity directing his own screenplay, Trump again appears in the Plaza, another attempt to blur the distinction between the person and his most cherished properties.

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The Pickle took after Christopher Guest’s The Big Picture, landing fewer satirical punches, but its heart was in the right place, unlike The Little Rascals (1994), another transplantation of a TV product onto film by director Penelope Spheeris, after Wayne’s World and The Beverly Hillbillies. Like the latter, this was a dusty property in dubious need of resurrection, and this Little Rascals barred participation by any living and willing Our Gang personnel. Several old gags are recycled and strung together, though, including one about rich kid Waldo participating in a go-kart race, during which he calls his father, Donald Trump, who blandly smirks into a vintage cellphone that Waldo is “the best son money can buy.” It’s something you can hear Trump possibly saying to Jared Kushner at his wedding to favorite daughter Ivanka.

Whoopi Goldberg took on the iconic role of Buckwheat’s mother in The Little Rascals, and she’d star in Trump’s next two IMDB credits. The coupling, as it were, is retrospectively noteworthy considering Goldberg’s post-election comments on The View that the winner is a “fool” who shamefully strikes fear into the hearts of schoolchildren of color, and she reminded the people that it’s a civic duty to “vote his ass out.” In Eddie (1996), she plays a limo driver and megafan of the woebegone New York Knicks who wins a contest to coach the team for a half, then lands the job when she proves successful. Trump’s brief cameo is a TV news interview that once again feigns poking mild fun at his ego but only flatters and supports the persona, as he says that “hiring Eddie was my idea from the beginning,” an instance of taking undue credit that would later be echoed most egregiously when he claimed credit for “finishing” the racist birther movement with which he made his political name. In the faux-progressive The Associate (1996), written by Nick Thiel (no relation to Peter, thwarting a juicily facile connection), Goldberg overcomes Wall Street sexism by adopting a successful male persona (the facile connection to Trump there is obvious). Trump appears as an associate of her white male privilege-boosted rival (Tim Daly), who tries to use the former’s yuge reputation to score the best table at a high-powered Manhattan restaurant.

Through the mid-90s, Trump continued to alternate between successes and failures via his casinos, beauty pageants, golf courses, smattering of real estate holdings and licensing of his name and the tinsel “Trump” brand, which remained strong enough to be referenced by rapper Raekwon on the classic Only Built for Cuban Linx (“Guess who’s the black Trump?”). Trump shows up in Mark Christopher’s 54 (1998), about the famous New York club at which Trump was a fixture in the 70s, learning life lessons from Roy Cohn and being photographed (always sober and joyless) with a rotating cast of arm candy. Still of interest to fans of cameos and hammy-serious Mike Myers, 54 suffered from Miramax meddling and a sense of being Boogie Nights leftovers. Trump’s best film is Woody Allen’s despairing, hard-angled (but funny) screed on fame and feckless manhood, Celebrity (also 1998), shot in stark black and white by a nearly blind Sven Nykvist and featuring one of the best surrogate Woody performances, by Kenneth Branagh. For once, the joke is on Trump here, as the film tears into the emptiness of the undeservedly famous. In a scene at posh Le Bijou restaurant, he reaches into his now well-known shallow pool of limited vocabulary when he tells reporter Judy Davis that he’s “working on buying St. Patrick’s Cathedral, maybe doing a little rip-down job and putting up a very, very tall and beautiful building.”

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Trump was off the big screen from 1999 to 2001, years in which he transitioned from Marla Maples to Melania Knauss, his father died, he founded a modeling agency and he began dipping his toes into presidential politics as a member of the Reform Party. In Ben Stiller’s medicinal post-9/11 riff on vapidity, noted expert Trump again appears being interviewed for TV, somehow not crediting himself with the model’s success when he says, “Look, without Derek Zoolander, male modeling wouldn’t be what it is today” as model Melania beams at him. In one of four films made with Hugh Grant, writer-director Marc Lawrence inserts Trump as an asshole associate of Grant’s fellow real estate tycoon in Two Weeks Notice (2002). At a party, Trump knocks Grant for being dumped, and again his humorlessness and alienation from human emotions shines through in his inability to make a single convincing facial expression.

That alienation is crucial, because for all of the efforts to pump up, perpetuate and normalize (as this article itself does, in its minor way) the Trump brand and persona, the man himself remains one of the weirdest critters alive, someone whose inner life you don’t know, and don’t want to. (There’s an anecdote about his MO on dates—having brought the woman home, he likes to go upstairs with a bag of candy and watch TV alone.) President Trump has an empowered new weapon by his side in the person of White House Chief Strategist Steve Bannon, a shrewd exploiter of hate with an extensive IMDB page of his own. But it doesn’t matter what Trump the man is like, because the bastard media creation that is “Trump” was able to seize on a vulnerable American populace in a particular moment. The shorthand “rich guy” stand-in that aided many a screenwriter in need of a quick gag is now the hateful extended cameo that will only end with its destruction or ours.