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Dave Letterman once really enjoyed having business mogul Donald Trump on his late-night show — so much so that he invited him on over 30 times during his 33-year run. But it’s been almost four years since he hosted his last show, and since then his view of Trump has changed significantly.
During his twelve years as the host of NBC’s “Late Night With David Letterman” and over 21 years with CBS’ “The Late Show with David Letterman,” the last episode of which aired on May 20, 2015 — just a few weeks before Trump announced his presidential run — the famous host had Trump on dozens of times. But when asked about Trump’s frequent appearances on The Hollywood Reporter’s “Awards Chatter” podcast, Letterman made clear that his opinion of his former guest has darkened dramatically.
“One guest that you had on more than 30 times between the two shows over the years was one Donald Trump,” said host Scott Feinberg. “And one time he was complaining about the way New York was being run, and you told him, ‘Listening to this stuff, it seems to me that you are dying to get some public platform to superimpose those feelings on the American awareness.”
Calling the comments “prescient,” Feinberg asked Letterman about his “overall impressions” of Trump over the years.
“First, 30 is the number between the two shows?” Letterman asked, incredulous. When Feinberg repeated that it was “more than 30,” Letterman exclaimed: “Wow! You’re welcome, America.”
That line got a laugh out of Feinberg, but that was about all the levity Letterman could muster before unloading on his former guest. Trump, said Letterman, used to be able to “take a punch,” even when he made fun of him for being a “slumlord,” “evicting elderly women,” and having an over-the-top hair-do — and the late-night crowd loved it.
“I think he just liked being on TV,” said Letterman. “I had no sense that he was the soulless bastard that he’s turned into.” Feinberg laughed at that line too, but Letterman didn’t join in. “Because then he could laugh at himself… Now I was not a student of his history or his background — just to me, as a talk show guest, [he] just seemed like fodder.”
Saying people always ask him if he would like to talk to Trump now, Letterman said, “I would.”
“I would just like to say, ‘Don, it’s Dave. Remember me? I want to talk to the real Donald Trump,” he said. “Because I now don’t know which is the real Donald Trump. And if the Donald Trump that I was talking to 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?! Who says okay now you’re going to behave like this?”
“He used to be kind of like the boob of New York that pretended to be wealthy — or we thought was wealthy,” said Letterman. “And now he’s just … he’s a psychotic. Is that putting too fine a point on it?” (Listen to the podcast here; relevant segment begins around 51-minute mark.)