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Here’s How Dave Letterman Responded When He Was Told He Had Donald Trump On His Show Over 30 Times

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.)

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10 Comments
  • Mary says:

    Jealous much, Dave?

  • kat says:

    It’s more like Letterman is the soulless bastard. Pres. Trump has done good things for our country and only moron Democrats refused to acknowledge it.

  • Dave sounds like a spoiled demorat Trump is doing what the spineless demorats wont we have need a president like him for a long time one who puts Americans first

  • Notalib says:

    So Dave, I assume he got you ratings and helped you. Now you attack him? You are kind of an old POS. Besides, who cares what you have to say.

    Trump is doing right by our country. You liberal/Democrats are doing your best to tear it down and don’t care how much damage you create.n

  • Dr. Jerold Theis says:

    As an individual Letterman is entitled to his opinion. Unfortunately the media gives too much exposure to the opinions of celebrities.

  • GARY SCHUY says:

    David Letterman. Do us all a Favor and retire. You are getting boring. Try something more original.

  • Steve H says:

    Trump doesn’t need to be coddled, if he’s changed it because of the incessant attacks that the media and democrats have been barraging him with. The difference between David Letterman and Donald Trump is that Donald is trying to make a difference. Letterman on the other hand is playing stupid and is promulgating the lefts agenda. I wonder what Letterman would do if he was being attacked like Trump is? Grow some balls David, stand up for your friend. Don’t cower in the corner and allow the media to devour our president.

  • Madeleine says:

    David letterman and all the other liberals who were sucking the Economy dry, have short memories. President trump has never changed. Everything he said 30 years ago about how Politicians were messing up the Country, he still says and its true. And one by one, he is fixing the problems, in spite of tremendous opposition in the Country and across the seas of the Deep dark State wanting to remove God, family traditions, National Pride and History and individual ability to think and hope!

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