He continued: “I think just for safety’s sake it wouldn’t be a good idea.”
Colbert, who had the president on his CBS late-night show almost four years ago, is just the latest entertainer who has reconsidered how and whether to give airtime to Trump in a comedic setting. In recent months, hosts including Colbert’s predecessor, David Letterman, and NBC’s Jimmy Fallon have expressed regret for inviting Trump on their shows, appearances that exposed millions of viewers to him in a more lighthearted way than a serious news interview.
Trump’s first and only appearance on Colbert’s show, which came as he was still seen as a long shot GOP candidate, drew decidedly mixed reviews.
When Colbert walked onto the set of “The Late Show” on Sept. 22, 2015, and announced to a raucous audience that “Donald Trump is here,” the bespectacled host from South Carolina had only been at the helm of the popular late-night program for about two weeks. As TV critic Brian Lowry wrote in Variety at the time, Trump’s appearance on the show was an “eagerly awaited” event.
On one side of the desk was a comedian who had developed a reputation for “piercingly intelligent satire,” as the Guardian put it. And in his guest chair would be the butt of many of his biting jokes — a brash New York real estate mogul and reality TV star-turned-unlikely presidential candidate.
“One day, I might be able to tell my grandkids I interviewed the last president of the United States,” Colbert quipped in his monologue at the top of the show.
But as Trump made his way to his seat, pausing to give a quick double thumbs-up to the cheering crowd, a smiling Colbert greeted him with a hearty handshake and kicked off the segment by thanking his guest.
“I want to thank you, not only for being here, I want to thank you for running for president,” Colbert said, drawing a chuckle from Trump. “I’m not gonna say this stuff writes itself, but you certainly do deliver it on time every day.”
“I work hard at it,” Trump said, grinning.
Despite Colbert pressing Trump on his not-so-warm welcome from the Republican Party and whether he seriously wanted the job, the interview remained cordial. Colbert cracked jokes (“And having to ride on Air Force One can you imagine? The smell of all those reporters who’ve been on there, you’ll have to have it fumigated.”) and Trump got to sell himself as a serious contender (“I would like to do it not because I want it but because I think I can do a great job.”).
Following a commercial break, Colbert even apologized to Trump.
“I’ve said a few things about you over the years, that are, in polite company, perhaps are unforgivable,” the host said.
Trump interrupted to say that there were “some nice things,” prompting Colbert to retort, “I don’t remember saying anything nice. But anyway, I hope you’ll accept my apology.”
But after Trump accepted, Colbert put him in the hot seat: Was there anyone he wanted to apologize to?
“Uh, no,” Trump said, quickly adding, “Maybe the audience, how about the audience?”
Later, Colbert intensified his jabs at Trump, especially when the conversation shifted to his proposed border wall. Colbert also pushed him on his repeated false claims that President Barack Obama was born outside the United States.
“I’m going to throw you up a big fat meatball for you to hit out of the park right now,” the host said. “This is the last time you ever have to address this question if you hit the ball, okay?”
“I want to hear this one,” Trump replied.
“Barack Obama: Born in the United States,” Colbert said, pretending to lob the imaginary meatball into the air. “Go.”
Trump, however, refused to answer, only saying, “I don’t talk about it anymore.”
As The Washington Post’s Emily Yahr reported, Trump’s sole guest appearance on the show — he phoned in for a short segment in 2016 — drew 4.6 million viewers but was met with some critical reactions.
Lowry wrote in Variety that Colbert brought “something new and extraordinarily timely to late-night TV.”
“Call it the art of the funny, not fawning interview — a chat that conjures laughs without completely sacrificing substance,” he wrote, noting that the episode was “in a way, a win-win for both men.” According to Lowry, Trump “exhibited at least some sense of humor about himself, while still getting in plenty of his talking points” and Colbert wasn’t shy about airing his skepticism of some of Trump’s policies.
Others argued that the host had been too soft on Trump.
“Colbert was trumped,” an Atlantic article proclaimed. A piece in the Guardian suggested that “audience members who tuned in on the promise of interesting friction” likely came away disappointed.
Since then, Colbert has emerged as one of the president’s most vocal critics. Now, Colbert’s monologues are chock full of blistering commentary about Trump and his administration, and the president has noticed. In 2017, Trump blasted Colbert as “a no-talent guy” in an interview with Time. Last year, he couldn’t even bring himself to say the host’s name when insulting him and other late-night personalities, only calling him “that guy on CBS.”
In a 2018 interview with Rolling Stone, Colbert said he was “very happy” with how his show handled Trump’s appearance.
“I was determined when the show began to lay down my sword and shield by the riverside, to see whether there was some way to have a public conversation that didn’t end up in fighting,” he said. “But I was determined to not stick a knife in.”
Still, Colbert expressed reservations about doing it again.
“I’m not sure if I’d ever want another bite of that apple, though,” he said. “Talk about sipping poison. Because I’m not sure if there’s any way for you to bite that apple and not get his disease.”