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The tragicomedy of Donald Trump on Saturday Night Live

In so many ways they were made for each other, as if a casting director considered Donald Trump and Saturday Night Live side by side and said, Yes, I can work with this. Few people have been impersonated on the show more often, or by more actors — six, at last count. He is the rare novelty guest to have hosted twice: once in 2004, to promote The Apprentice, his reality television show, and again in late 2015, to soften perceptions of a presidential campaign widely seen as alarming. After the second appearance, some on the left accused SNL of helping to “normalize” Trump, which (the theory proceeds) partly cleared the way for his election, though his having been a celebrity for three decades may also have had something to do with it. Many on the right, meanwhile, consider SNL to be one of the many cultural bacteria poisoning America’s view of conservatism. Either way, each time Trump has done the show, the ratings have been boffo. But who used whom, exactly, and for what?

Like Trump, SNL has had rises, falls, and unlikely comebacks. Like Trump, it has had woman problems. John Belushi wouldn’t perform sketches written by women; his castmate Jane Curtin later recalled, “He told me women were not funny.” * Like Trump, SNL has struggled with race: Garrett Morris, the only black member of the original cast, was underused throughout his years on the show, and even an incandescent young Eddie Murphy initially languished as a featured player. With Weekend Update, which was unlike anything before it became like everything, SNL also shares Trump’s pioneering interest in fake news.

Photograph of Amy Poehler, Kenan Thompson, Donald Trump, Seth Meyers, and Maya Rudolph during Saturday Night Live’s “Donald Trump’s House of Wings” sketch, April 3, 2004. © Mary Ellen Matthews/NBC/NBCU Photo Bank/Getty Images

SNL premiered in 1975, a year before Trump was first profiled by the New York Times. A Queens kid who began his career wanting to be an entertainment-industry mogul — Trump once described his “ultimate job” as “running MGM in the Thirties and Forties” — he instead fell back on the family business, real estate. To the Times, Trump claimed that he was worth $200 million when his taxable income was $2,200 a week. He claimed that his heritage was Swedish when it was actually German — a habitual ethnic elision; Fred, his father, rented to many Brooklyn Jews. He claimed that he had graduated at the top of his class at the Wharton School when he received no honors. Three lies, none challenged. And off we go.

Thanks to guile and chutzpah, by the time Trump was thirty he’d pulled off a few brilliant development deals in Manhattan — most of them distressed properties scooped up on the relative cheap and technically controlled by Fred. He’d also been involved in his father’s litigation against the Nixon Administration, which alleged that the Trumps were engaging in discriminatory practices against hopeful black renters. Their lawyer, Roy Cohn, accused the FBI of “Gestapo-like tactics,” which was not common rhetoric in the early Seventies, when plenty of people in the Justice Department had fought to rid the world of Nazism. A decade later, Trump became a tabloid staple for his disastrous foray into Atlantic City, New Jersey; his lawsuit against the N.F.L.; his near bankruptcies; and the women he dated, married, and bitterly divorced.

The Eighties also saw Trump begin his long engagement with politics. In the lead-up to the 1988 presidential election, he journeyed to New Hampshire with the clear purpose of one day running. In a speech, he implied that he would make a good chief negotiator between Ronald Reagan and Mikhail Gorbachev. David Cay Johnston, an investigative journalist, reported hearing a man in one of Trump’s Atlantic City casinos call out, “Be our president, Donald!” while he rode up an escalator. The prospect of a Trump candidacy intrigued certain Americans, and Trump knew it. “If the right man doesn’t get into office,” he said at the time, “you’re going to see a catastrophe in this country in the next four years.” All that was missing were boasts of his investigators scouring the Kenyan highlands for clues.

Naturally, Trump became a subject of interest to SNL. In 1988, the show aired a sketch called “A Trump Christmas,” in which Phil Hartman and Jan Hooks played Donald and Ivana succumbing to holiday ennui. It’s not very good — it turns on an update of O. Henry, with Donald having sold his yacht to purchase a door for Ivana’s mansion and Ivana having sold her mansion to buy an anchor for Donald’s yacht — but what’s fascinating is the way Hartman chose to portray him. The broad gangster-flick accent sounds nothing like Trump, then or now. Further, his Trump refers with ease to a fifteenth-century Italian sculptor and has only one question for Ivana when she refers to her recent purchase of pearls: “Cartier or Buccellati?”

The following year, during the show’s fifteenth-anniversary special, Chevy Chase wandered into the audience and spilled popcorn on a tuxedoed Trump, who gamely smiled and raised his fist — a little in-joke for the benefit of New Yorkers and readers of Spy magazine. Between this and Hartman’s impression, viewers of SNL could have felt certain that the one thing this outer-borough epicure would never be was a figure of world-historical significance.

How sincere Trump’s political aspirations have ever been remains an open question, but it bears noting that his flirtations with the electoral process have tended to coincide with personal downturns. In the Nineties — a period that let SNL poke fun at an endlessly appetitive president, along with a gallery of Clinton agonistes primed for caricature, such as Newt Gingrich, Linda Tripp, and Ken Starr — Trump was nearly destroyed. He lost control of the West Side Yard (which was central to his bid to compete with the Ravitches, the Dursts, and other giants of New York real estate), the Plaza Hotel (creditors reclaimed it), and much of his personal fortune (at one point he had to borrow money from his siblings to cover his office expenses). His annual salary at the time may have been as little as $200,000. In less than a decade, he’d gone from The Art of the Deal to being in hock for close to a billion dollars. Trump emerged from this gauntlet admittedly cautious about the tenuousness of his fortune. “Because I see what can happen,” he told Timothy L. O’Brien, his biographer. “In the ’80s, I didn’t even appreciate it. I figured, this is the easiest fuckin’ thing.”

NBC saved him. Trump’s least fractious business negotiation was in 2003, with Mark Burnett, the reality TV producer. When informed of the handshake terms for the debut season of what became The Apprentice — Trump’s per-episode fee was a relatively paltry $50,000 — Trump’s people wanted to wring more concessions from Burnett, but Trump uncharacteristically shut them down. A deal was a deal, and he’d finally found his true calling: role-playing the world’s greatest businessman for the National Broadcasting Company.

NBC chose to depict the Trump Organization as a firm with global wingspan and Trump himself as a chief executive with a peerless eye for talent. This squares with the estimation of few outside the Trump Organization. One Apprentice contestant recalled an encounter with Trump’s COO, who began his career at the company as Trump’s security guard. When he was asked to produce a company org chart, he wondered, “What’s an org chart?” In the opening narration of The Apprentice, Trump can be heard saying, “I’m the largest real estate developer in New York,” but he wasn’t and never was, not even at his apogee. The building most prominently featured in the title sequence — Trump International Hotel and Tower — isn’t property that Trump owns. As for the six-figure salaries paid to the competition’s victors, they were line items covered by NBC.

In 2004, with The Apprentice a success, Saturday Night Live extended its first invitation to Trump: two American institutions, adept provocateurs, waist-deep in network synergy. According to O’Brien, during rehearsal, Trump had a question for Lorne Michaels, the show’s creator: “Which is bigger, a television star or a movie star?” Michaels explained to Trump that a television star’s wattage was necessarily brighter, as he was seen by a larger audience. “I never thought of it that way,” the newly minted television star responded with delight. Then, like a high-living mobster relishing the prospect of his own inevitable hit, Trump predicted the demise of the career he was only beginning to enjoy. “Someday,” he told Michaels, “NBC will call me and say, ‘Donald, the ratings are no good and we are going to have to cancel.’ ” Michaels offered a correction: “They won’t even call.”

“Nobody’s bigger than me,” Trump declares during his SNL opening monologue. “Nobody’s better than me. I’m a ratings machine.” He winks when he says this; you’re willing to believe that he is in on the joke. The crowd is laughing along. They seem to sort of like this Trump, only five years since he’d approached ruin. He goes on to tell the audience that television is just a “hobby,” and that he’s primarily occupied with “my real estate holdings, my best-selling books, and making love to women who’ve won prizes for their beauty.” Laughter. “But not anymore, because I have a great girlfriend.” Laughter. And then an unscripted aside: “That’s true!” More laughter. His hand is raised and his lips are pursed as he prepares to deliver his next line, but then the hand drops. He’s puzzled why anyone would laugh at him having a great girlfriend. (He’d been on-again, off-again with the Slovenian model Melania Knauss for six years.) “What the hell is this?” Trump asks, seemingly quite hurt, looking around. Behind him, the members of the house band — not future Trump voters, one imagines — are all smiling broadly. Wait. Is it — could it be — that this Trump is actually, almost, charming? “I can’t win,” he says, throwing up his hands as the crowd applauds. Then he jokes about firing people.

Trump featured heavily in many of the sketches that followed: a bit parodying Live with Regis and Kelly, in which he has to be physically restrained from leaving the guest chair, lest the show’s ratings drop in his absence; a “Prince and the Pauper” reboot in which Darrell Hammond’s Trumpian plutocrat swaps places with his janitor, who’s played by Trump. “Who did your decorating?” Trump asks Hammond. “Saddam Hussein?”

It’s clear that Donald Trump is a mother lode of comic riches, but what kind of comedy is Trump’s, exactly? If satire presents us with irresistible social forces brought to their logical — if not plausible — extreme, then Donald Trump is a golem of ideally satirical proportions. If you want farce, Donald Trump has you covered, with his lurching handshakes and his heartrending inability to spell. For aficionados of prop comedy, behold the hair, the hands, the appallingly long and scotch-taped tie. Or perhaps you’re in the mood for a comedy of manners, in which the rigid mores of a bluenosed elite are tweaked and bopped by a rowdy playboy, to lusty cheers from a crowd thick with red trucker hats. Or maybe you want Kubrickian black comedy? If so, enjoy a long, chilling look at the man who can now end the world with a tweet. Donald J. Trump — the name itself a Dickensian charactonym — is not a politician, a businessman, or an entertainer but a skilled character actor. The one thing about him that’s not hilarious is that he’s real.

At the end of the 2004 show, after Trump wishes everyone a good night and the credits roll, he can be seen embracing Seth Meyers, who, thirteen years on, would emerge as one of his chief comedy antagonists. (Trump would describe him as “somebody who in my opinion has absolutely no talent.”) And there’s Trump shaking hands with, of all people, Questlove from the Roots. And then there came a great earthquake, and the full moon became like blood, and the stars of the sky fell to the earth.

Despite SNL’s reputation as a liberal bastion, a number of conservative or iconoclastic writers and performers have passed through its halls: the revered sketch writer James Downey, the Weekend Update hosts Dennis Miller and Norm Macdonald, and the cast members Joe Piscopo and Victoria Jackson, to name a few. Downey has complained that the show tends to handle people on the left with kid gloves, portraying them as, at worst, “too brainy and intellectual.” (We know of at least one Democrat who acted on his SNL send-up: Al Gore and his campaign staff are said to have watched and rewatched a sketch about his first debate with George W. Bush in an attempt to understand why he’d been mocked.) As for the politics of most of the conservative cast members, they were rarely evident while they were on the show. But Macdonald, who had an embattled tenure at Update that ended with his termination by NBC management, seemed to relish sticking his thumbs in the eyes of his largely liberal audience. During an episode in 1997, he joked about a custody battle between a transgender woman and her wife. “Hmm,” he said, “I wonder who’s gonna win this case. The mother of the two children, or the guy who had his penis twisted into a fake vagina” — a tasteless joke even for the time. More recently, Macdonald has suggested in interviews that SNL misrepresents Trump. He told New York magazine, “I don’t like agenda comedy.”

Michaels, for his part, has long been ambivalent about playing to liberal consensus. When Trump was elected president, he gathered the cast and writers to remind them of something: “Half the country voted for Trump, and our show’s for those people as well. It’s not just for people who didn’t want him to be president.” A number of them appear to have internalized this. In an interview with Esquire, the cast member Michael Che — who, during the campaign, was a reliable tonic to liberal overconfidence in Hillary Clinton’s chances — claimed that he wanted to hit Democrats harder than the show had in the past. This put Che in concert with Trump, who has often complained of SNL’s unfairness. “Oddly, I agree with him,” Che said. On Weekend Update, shortly before the election, Che said this: “If we have a war, I don’t want a bunch of snarky liberals out there fighting for me, with their good taste and skinny jeans. I want somebody that dresses like John Cena, listens to Nickelback, and has never met an Asian. That’s who’s gonna kick some ass. I’ll call liberals when I want a pointed think piece.”

Alec Baldwin as President Donald Trump and Mikey Day as adviser Steve Bannon, February 4, 2017. Photograph © Will Heath/NBC

Colin Jost, Che’s Weekend Update cohost, has also tweaked liberal sensitivities. In one segment, he claimed that a new feature of Tinder, the dating app, which provides users with thirty-seven gender-identity options, was called “Why Democrats Lost the Election.” The joke led to a social-media flaying. Critics are free to consider the line mean-spirited, but it wasn’t advocating the abandonment of cherished liberal values. It was lamenting the excruciating paradox of cherished liberal values. There are legitimate moral reasons not to poke fun at the less powerful and marginalized, but the goals of comedy probably shouldn’t align exclusively with those of the Southern Poverty Law Center.

In its depictions of presidents, SNL has evolved, or maybe devolved. When Chevy Chase did Gerald Ford, he didn’t get into makeup; Dan Aykroyd’s Jimmy Carter sometimes had a mustache. It was Reagan’s handsome crags and brilliantined pompadour that pushed the show toward prosthetic comedy, with Piscopo, Hartman, and Harry Shearer all taking a turn. As performers’ transformations grew more overt, the impersonations became fussier. For Darrell Hammond’s endlessly lip-biting Bill Clinton, empathy seemed a long-mastered parlor trick; Will Ferrell’s flinty yet childlike George W. Bush had the strange effect of making the man himself seem more sympathetic. Alec Baldwin’s Trump has been most like Dana Carvey’s H. W. Bush: a presidential impression that begins in a place of phonic approximation but escalates to spasmodic, recursive mania — an impression of an impression. While Carvey’s Bush was silly and affectionate enough to get him invited to the White House, Baldwin’s every gesture and tic as Trump seems shaped by scalding bile.

Baldwin has said that until he was standing on his mark for his first dress rehearsal as Trump, he had no idea what he was going to do or how he was going to do it. He decided to focus on capturing his essence — that of a man “who’s always searching for a stronger, better word, and he never finds it.” As it happens, the word that helped Baldwin lock in his vocal performance was “China,” which his Trump pronounces “Jhina” — and this was weeks before the emergence of the Access Hollywood tape that would forever connect Trump to assaulted vaginas in the hellscape of American consciousness. During the sketch, Kate McKinnon’s Hillary Clinton looks on aghast at the unhinged, Grinch-faced man saying, “Huge. Huge. Huge Jhina.” What’s most striking about the performance is how closely Baldwin’s dialogue hews to the transcript of the actual debate. Near the end, Michael Che’s Lester Holt asks McKinnon what she thinks. McKinnon pauses, smirks, and says, “I think I’m going to be president.” What was once a joke at Trump’s expense now has the solemn, fated ring of a line from Aeschylus.

In 2015, when Trump announced his candidacy for the job he’d always eyed during low times, SNL’s writers appeared to assume that his crudity and nihilism made him unelectable. The invitation to host, in November, came as he was polling at around 25 percent among Republicans. Nate Silver, the statistician, wrote at the time, “That’s something like 6 to 8 percent of the electorate overall, or about the same share of people who think the Apollo moon landings were faked.” The idea that seven months later Trump would clinch the G.O.P. nomination, much less become president, still seemed like it belonged to cryptozoology.

During Trump’s opening monologue, everything was a less funny elaboration of the core joke of his 2004 appearance: Sure, I play a megalomaniacal lunatic on television and in popular culture, but I’m here to demonstrate that I’m in on the act. But watching him this time, you’re not certain that he is.

“You’re a racist!” Larry David, who wrote for SNL before going on to Seinfeld and Curb Your Enthusiasm, shouts at Trump from offstage, interrupting his monologue. Trump and David proceed to do their scripted bit, but it seems evident that David means what he says: At the end of the show, during the farewell sequence, David turns away from Trump, apparently to avoid shaking his hand. On SNL’s staff, a few were not happy that Trump was there. During Weekend Update, Che cracked a birther joke, which was followed by a mock-whispered “I’m talking about the guy hosting the show.” Months later, Taran Killam, a cast member, went public with his displeasure (after being let go by Michaels), claiming that Trump was impossible to work with and didn’t understand any of the jokes. “The president,” he said, “is a moron.”

As episodes go, Trump’s second SNL appearance is not as gruesome as the time Joey Buttafuoco turned up or Paris Hilton hosted, but it’s a brutally unamusing experience nonetheless. The one interesting sketch takes us inside the Trump White House in 2018. The premise is that everything is great. “Prosperity’s at an all-time high!” President Trump is told. “In two years, you really made America great again.” And then the best joke of the night: “Everyone loves the new laws you tweeted.” The president of Mexico arrives, bearing a check for the wall. The secretary of the Interior, played by the real-life Ivanka, describes her ongoing efforts to cover the Washington Monument in gold-mirrored glass. “Wow,” Trump says. “That’s gonna look so elegant.”

It’s strange, watching a dystopian satire unblushingly performed by the very people it is attacking. Is this what descent into autocratic kleptocracy looks like, with thieving mountebanks joking about what they’re going to do while an audience overwhelmingly opposed to them politely applauds? At the end, Trump says, “If you think that’s how it’s gonna be when I’m president, you’re wrong. It’s gonna be even better.” For once, even he seems to realize it’s a laugh line.

Throughout the episode, Trump turns out to be uniquely dreadful at performing Donald Trump, which should be distinguished from being Donald Trump. Stick him in front of fifteen thousand people in a stadium and tell him, “Be Donald Trump,” and he’ll sail away from his teleprompter into a sea entertainingly clogged with the sargassum of his ego. But place him in dramatic context — give him other people to deal with — and the fragile contraption comes apart. In the end, he wasn’t funny on SNL because he didn’t get to do his own material.

Saturday Night Live’s last season has been called its most relevant and funniest in decades. Ratings were 30 percent higher than the previous year’s, and the show earned a record twenty-two Emmy nominations. Its cast was one of the most versatile in SNL history; in McKinnon the show employs a singularly great comic talent. Politically, SNL displayed admirable nuance. The “Black Jeopardy” sketch, with Tom Hanks’s Trump-loving contestant Doug forced to compete against two black women in categories such as “They Out Here Saying,” “I’m Gonna Pray on This,” and “White People,” was an effective plea for underclass solidarity. (It was also, however, a skillful piece of anguished condescension.) The latest incarnation of Weekend Update was as reliably sharp as any of the innumerable satirical news shows that imitate it, and the short films and fake commercials were better than ever.

But the live sketches consistently fell short. An SNL sketch often turns on a single idea and works it to the point of sublimity or exhaustion. When successful, a sketch can feel galvanically unrepeatable in the manner of great theater. When less successful (or simply bad) it can exude an aura of flailing pointlessness. What’s terrifying about a live sketch is that no one knows if it will be any good until it’s on its feet. A typical week of SNL prep sees upwards of fifty proposed sketches get whittled down to fifteen, and then twelve, and then ten, and then eight, and then showtime. Many fully propped and staged sketches are cut after the dress rehearsal, when they’re tested before a live audience. Sketches are rewritten until the moment they go live, and performers are strongly discouraged by Michaels from ad-libbing, since camera cuts are cued to certain lines.

The nervous, we-might-flop energy generated by being live can seem today like a Seventies novelty that no longer creatively benefits the show. But what live television brings is a war-room atmosphere, which makes SNL, especially in politically restive times, uniquely responsive and newsy. Indeed, virtually every Trump and Trump-related sketch of the past year was treated as if it were breaking news. SNL, which for decades had to rely on an audience that stayed home on Saturday night, has gained influence from the ways in which social media has altered viewing habits. Thanks to streaming platforms, I haven’t seen SNL at its appointed hour in a decade, and I am not alone. On YouTube, popular sketches have often been watched tens of millions of times.

Ours is a moment when the consumption of content often feels like the cognitive equivalent of a full-time job. We view footage of Richard Spencer, the white nationalist, getting punched in the ear, we read the think piece about whether that was okay, we watch Stephen Colbert’s monologue, we link to John Oliver’s latest — and there goes the morning. SNL’s political sketches in particular have become the artillery rounds of the creative class, subjected to morning-after analyses on culture websites, shared on Facebook, tweeted at political opponents. What we once knew as a twistedly innovative variety show is long gone, and what has replaced it is a machine producing all manner of Trump-related media. Jost has admitted to feeling “like a war profiteer at times, because we’ve benefited from a situation that’s so tough.”

If nothing else, SNL’s brand of Trump-era comedy has helped reassure some of us that we’re living in the same reality. This is probably why the left keeps wondering whether satire might save the day, having mistaken it for a potent form of counterattack. But as the new season begins, we should acknowledge that the show can’t compete with Trump, who might be the most successful stadium comedian in history. When he says outrageous things about subjects and groups that progressives and liberals have walled off from even the mildest ridicule, when he calls a Latina beauty queen “Miss Housekeeping” or pantomimes the physical handicap of a reporter, he knows perfectly well what he’s doing, the table he’s turning. His brand of comedy — cruel and joyless and denuded of laughter — has become his cultural revenge.

’s article “My Holy Land Vacation” appeared in the July 2016 issue of Harper’s Magazine. His essay collection Magic Hours will be reissued in December by Vintage.

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