'He's just a psychotic': Letterman looks back with regret on his many Trump interviews

Donald Trump and David Letterman, Late Night with David Letterman | Photo Credits: NBC, NBCU Photo Bank via Getty Images Donald Trump and David Letterman, Late Night with David Letterman | Photo Credits: NBC, NBCU Photo Bank via Getty Images Photo: 2015 NBCUniversal Media, LLC Photo: 2015 NBCUniversal Media, LLC Image 1 of / 3 Caption Close 'He's just a psychotic': Letterman looks back with regret on his many Trump interviews 1 / 3 Back to Gallery

It is late 1987 and David Letterman is in his element - cameras rolling, a new guest moments away from joining him onstage, and a biting joke about to fire out from his lips.

Since debuting as the host of NBC's "Late Night" in 1982, the comedian had been lobbing sarcasm and irony, delivered in an Indiana aw-shucks style, at the absurdities of the "greed is good" era. His next guest is a plump target, a walking, talking embodiment of the bloated egos and burning vanities of the 1980s.

"Our next guest tonight has enough money to give everyone in the audience a million dollars," Letterman says, his face splitting in a huge smile at the absurd statement as the audience explodes in cheers.

As the applause continues, a crafty tech swings a camera to the stage's edge, where real estate developer Donald Trump is caught poking his head out from backstage to soak up the crowd's response.

"At the beginning of the show, I said you either love him or you hate him," Letterman says to his guest once he sits down. Trump, fresh off the success of his book "The Art of the Deal," is making his first visit to Letterman's show. "Now do you find that's true? Does everybody love you or does everybody hate you?"

"Most people love me, and few have great distaste for me, David," Trump says, his voice quiet - a contrast to the harsh carnival bark he'd use decades later in politics. "I sort of speak my mind."

The December 1987 episode launched a decades-long on-screen dance between the two men. Trump would reportedly go on to appear more than 30 times on both Letterman's "Late Night" and its CBS successor, "Late Show."

"More than 30? Wow! You're welcome, America," Letterman said this week when he was told about the stat on The Hollywood Reporter's Awards Chatter podcast. But in his interview on Tuesday, the 72-year-old comedy legend left little doubt about where he falls on that question he asked Trump back in 1987: Love him or hate him?

"I had no sense that he was the soulless bastard that he's turned into," Letterman said on the podcast.

Letterman is far from the only media personality rehashing his history with Trump in light of his ascent to the presidency.

Trump landed in politics with a persona - wealthy playboy, savvy tycoon, gruff truth-teller - ironed into place by decades of media appearances. From Letterman's guest chairs to Howard Stern's radio show to the board room of "The Apprentice," America got regular doses of Trump well before he ran for office. Letterman and others like Stern beamed Trump to the masses for entertainment. For Letterman, it's not funny anymore.

"He used to be kind of like the boob of New York that pretended to be wealthy, or we thought was wealthy, and now he's just a psychotic," Letterman told THR. "Is that putting too fine a point on it?"

Trump popped up on Stern's immensely popular radio show on dozens of occasions between 1993 and 2015, calling into the show and appearing in the studio. Often, the shock jock maneuvered the conversations toward sex, with Trump boasting about his alleged bedroom antics.

"He's one of the best guests ever," Stern told "CBS Sunday Morning" last month. "As a radio guest, he says whatever pops into his mind. And he understands how to play that game - doesn't appeal to everyone, but it appeals to enough people, that style appeals to enough people, to turn them on."

Stern, however, did not let his affection for Trump as a guest cross over into his political decisions. In 2016, Trump asked the radio host to endorse him in his matchup against Hillary Clinton.

"I had to say to Donald on the phone - it was uncomfortable - 'I can't endorse you.' And I haven't heard from him since," Stern told "CBS Sunday Morning." "We don't talk at all."

If Stern cycled Trump in among the cartoon-like cast of regulars who fill up his airwaves, NBC's "The Apprentice" broadcast Trump as a business success to millions of American viewers - a portrayal that ran counter to facts.

Indeed, as the New Yorker's Patrick Radden Keefe documented last December, Trump's reputation was at a low point when he initially signed on for the show in the early 2000s. The show, created by "Survivor" producer Mark Burnett, rehabbed his image.

"I don't think any of us could have known what this would become," Katherine Walker, a producer on the early seasons of "The Apprentice," told Keefe. "But Donald would not be president had it not been for that show."

Letterman's own history with Trump is far more complicated. Over the decades, he regularly lampooned Trump on-air, entertaining viewers at the businessman's expense.

"He was a joke of a wealthy guy," Letterman told New York in March 2017. "We didn't take him seriously. He'd sit down, and I would just start making fun of him. He never had any retort. He was big and doughy, and you could beat him up. He seemed to have a good time, and the audience loved it, and that was Donald Trump."

But the host and Trump also tangled on serious issues. During the first term of the Obama administration, when Trump began publicly airing false claims about the president's birth certificate, Letterman openly criticized the mogul, even calling him a racist, according to the New York Times.

The comments led to a spat between the two celebrities, with Trump boycotting the show, the Times reported. In 2012, Trump returned to Letterman's stage, where the host apologized for his comments.

Letterman, however, had a biting comeback waiting. As the interview continued, the host steered into global politics, commenting on Trump's then-criticisms over China.

"I have nothing against China, I just hate that their leaders are so much smarter than our leaders," Trump said at the time. "In 2016, we will not be the world leader anymore," he continued. "In 2016, China becomes the great economic power."

Letterman then pulled out a Trump-branded tie, noting that the product was made in China. Trump was left with an awkward grin on his face before his eyes jumped up in acknowledgment.

Despite his feelings today about the president, Letterman told THR he would still like to sit down with Trump for another interview in their long dialogue.

"I would just like to say, 'Don, it's Dave. Remember me? I want to talk to the real Donald Trump,' " Letterman explained. "Because I now don't know which is the real Donald Trump, and if the Donald Trump that I was talking to [back then] was the real Donald Trump, how do you get to be the guy he is now? Politics notwithstanding - let's just say everything is great and he's done a great job, but he still behaves the way he behaves - who behaves like that?"