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Alec Baldwin as Donald Trump on “Saturday Night Live.”
CreditWill Heath/NBC

For the 42 seasons that “Saturday Night Live” has been on the air, critiquing the show has not only been the preoccupation of comedy nerds but also every American’s national duty. No viewer, however, has seen his criticism of the show scrutinized — or had the show get under his skin — quite like President Trump.

Mr. Trump is the first president of the United States to take umbrage publicly at his portrayal on “S.N.L.” and fight back in real time (a phenomenon that began this past fall, when Alec Baldwin began impersonating him). That fraught dynamic is even more remarkable given that Mr. Trump has been lampooned on the program regularly for almost 30 years — he is as much of an “S.N.L.” character as Stefon, the Church Lady or Debbie Downer — and for a time he seemed to enjoy a friendly relationship with the show. So where did it all go awry?

With Mr. Baldwin about to host “Saturday Night Live” this weekend and the world waiting to see how (if at all) Mr. Trump reacts, here’s a look back at the complicated relationship between the chief executive and the comedy series he loves to hate.

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The Debut

Dec. 10, 1988

In their debut as characters on “Saturday Night Live,” Donald J. Trump and his first wife, Ivana (played by Phil Hartman and Jan Hooks), are the filthy-rich romantic leads of this parody of O. Henry’s “The Gift of the Magi.” Donald sells his yacht, the Trump Princess, to buy Ivana a gold, jewel-encrusted door for Mar-a-Lago, but Ivana has sold Mar-a-Lago to buy Donald a gold, jewel-encrusted anchor for his yacht. Though the Trumps are presented as wealthy, brand-obsessed philistines, the satire isn’t too pointed.

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The ‘Winner’

Feb. 17, 1990

Following an appearance by the real-life Mr. Trump at the “S.N.L.” 15th-anniversary special in 1989, when Chevy Chase charged through the bleachers to dump popcorn on his head, Mr. Hartman resumed the role in this sketch set during Donald’s divorce battle with Ivana (played again by Ms. Hooks). By now, Mr. Hartman had perfected the nuances — the pursed lips, narrow gaze and unplaceable New York accent — of a Trump character depicted as a shrewd casino huckster, who goads Ivana into losing her prenuptial agreement on a game of three-card monte. “Do you realize how badly you’ve been beaten?” he taunts her.

 

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The ‘Reform’ Politician

Oct. 2, 1999

With the maverick reputation of his independent Reform Party starting to fade, the businessman H. Ross Perot (Cheri Oteri) must find a new standard-bearer for the movement, and among the candidates he’s considering is none other than Donald J. Trump (played this time by Darrell Hammond). This prescient sketch had Mr. Trump’s political aspirations pegged early on, and it imagines him pitching a plan to replace the White House with a 90-story government facility and casino — “all brass and class,” he explains — called Trump House. For a campaign slogan, he suggests: “I Got It. You Want It. Come and Get It.”

 

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The Reality TV Star

Jan. 10, 2004

Two days after the premiere of “The Apprentice,” the dog-eat-dog NBC reality series that would propel Mr. Trump back into the cultural consciousness, Mr. Hammond played him again in an opening sketch. This Trump is a relentless self-promoter who traffics in moxie rather than established facts (“I just learned yesterday that my own Taj Mahal in Atlantic City wasn’t the first Taj Mahal, but I guarantee you it’s the best”), and his suggestions for improving NBC aren’t much more sensible. (“How does ‘NBC Nightly News With Donald Trump’ sound? Good, right?”) In a bonus cameo, Jeff Zucker, then NBC Entertainment’s president, is played by Jimmy Fallon, the future “Tonight Show” host and Trump interlocutor.

 

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The Janitor and the Chicken King

April 3, 2004

With “The Apprentice” now a Top 10 hit in the ratings, the flesh-and-blood Mr. Trump made a game first appearance as a “Saturday Night Live” host. “It’s great to be here at ‘Saturday Night Live,’” he told the audience in his opening monologue, “but I’ll be completely honest, it’s even better for ‘Saturday Night Live’ that I’m here. Nobody’s bigger than me. Nobody’s better than me. I’m a ratings machine.” After giving Mr. Hammond a few pointers on his Trump impression, he appeared in several comedy sketches, including a sendup of “The Prince and the Pauper,” in which Mr. Hammond played Trump and Mr. Trump played his own lowly doppelgänger, a janitor at Trump Tower. He also dressed in a bright yellow suit and tie, surrounded by “S.N.L.” cast members costumed as chickens, in a fake ad for Trump’s House of Wings.

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 The Hammond Era

October 2004 – December 2011

Over the next seven years, Mr. Hammond would portray Mr. Trump in more than a dozen sketches, some just silly and others more observant of his longer-term ambitions. The common denominator was Mr. Trump’s tendency for boastfulness: One skit from 2005 imagined him trying to film a commercial for Domino’s Pizza (“Personally, I think it’s the highest-quality pizza of the low-quality pizzas”); another, from 2011, pitted him against Sarah Palin (played by Tina Fey) in a debate among potential candidates for the 2012 Republican presidential nomination. Propositioning the Palin character to join his ticket, his Trump says, “If you want to be my vice president, all you have to do is sell more chili than NeNe Leakes over the course of a hot summer day in Times Square.”


The Candidate-Host

Nov. 7, 2015

When Mr. Trump returned to host “S.N.L.,” now as a contender for the Republican presidential nomination, the circumstances could not have been more contentious. He had given a polarizing speech announcing his candidacy, in which he said of Mexican immigrants: “They’re bringing drugs. They’re bringing crime. They’re rapists.” NBC, in response, had announced it was cutting its business ties with him and removing him as host of “The Celebrity Apprentice.” Despite hopes that “S.N.L.” might use this opportunity to take off its gloves, the sketches mostly went easy on the host (except perhaps during his opening monologue, when Larry David stood up from the audience to shout, “Trump’s a racist!”) After the broadcast, Mr. Trump tweeted that it had been an “amazing evening” with “electricity all over the place.”


The ‘Hit Job’?

Oct. 15, 2016

As Election Day loomed, Mr. Baldwin had already made two appearances as Trump — now the official Republican nominee — in satirical re-enactments of his debates with the Democratic nominee, Hillary Clinton (Kate McKinnon). But one segment got under Mr. Trump’s skin. After a sketch that depicted him as petulant, short-tempered (“Do you feel you’re modeling appropriate and positive behavior for today’s youth?” “No, next”) and tasteless (“Speaking of black men, you know who else should be in jail? Hillary Clinton”), Mr. Trump took to his Twitter account to push back at the show and his portrayal. “Watched Saturday Night Live hit job on me,”he wroteearly the next morning. “Time to retire the boring and unfunny show. Alec Baldwin portrayal stinks. Media rigging election!”


President Baldwin

Jan. 14, 2017 and Feb. 4, 2017

Mr. Trump’s victory on Nov. 8 did nothing to dissuade “Saturday Night Live” from its mockery of the next occupant of the Oval Office to end the war of words between the two combatants. After more of Mr. Baldwin’s cutting impersonations and more of Mr. Trump’s Twitter rebuttals, the conflict reached a new level six days before Mr. Trump’s inauguration with a sketch lampooning an awkward and pugnacious news conference. Mr. Trump pushed back at “S.N.L.” the next day, writing: “@NBCNews is bad but Saturday Night Live is the worst of NBC. Not funny, cast is terrible, always a complete hit job. Really bad television!”

But since he was sworn in as the 45th president of the United States, Mr. Trump has not indulged in any instant criticism of “S.N.L.” even after last weekend’s broadcast, which featured a devastating takeoff on the White House press secretary, Sean Spicer (in which Mr. Spicer was played by Melissa McCarthy), as well as an opening sketch, in which Mr. Baldwin and the “S.N.L.” cast brought to life a week of Mr. Trump’s diplomatic missteps. His Twitter account remains silent on the topic of “Saturday Night Live.” For now.



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