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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.)

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  1. MJ

    June 12, 2019 at 9:18 pm

    David Letterman is just like all other has been celebrities, he used Donald Trump for his ratings just like Oprah used him on her show, and then politicians like The Clinton’s and Mitt Romney used him for big donations to their campaigns. David Letterman is so “ nobody” who cares what he says or thinks? Oh, and he needs to rake around his own door, I recall what a sleaze bag he was during the scandal concerning him and a woman on his staff right after his marriage and birth of his son! Such a douche bag!!!

    • JAIME.

      June 12, 2019 at 10:20 pm


    • Arlene

      June 12, 2019 at 11:48 pm

      M J ~ thank you! I couldn’t have stated it better!

  2. Patrick Rodgers

    June 12, 2019 at 10:45 pm

    Letterman is just another in a long line of left wing liberal ass holes. Flash message to Dave Letterman. 63 million of us elected Donald Trump to clean up the shithole left in Washington by your Muslim in Drag President. Trump will be there for five more years so get used to it and quit sniveling.

  3. N

    June 12, 2019 at 10:50 pm

    ‪Expose, Boycott, Sue, prosecute and bring to justice all these deep state treasonous Godless NAZI commie liberal Muslim pedophilia demoncrats and RINOs post-haste,Patriots! Drain the rat infested swamp President Trump!‬

  4. LST

    June 12, 2019 at 11:02 pm

    Letterman has always sucked. I always watched Jay Leno, he was the best.

  5. Bird

    June 12, 2019 at 11:17 pm

    “He used to be kind of like the boob of New York that pretended to be wealthy — or we thought was wealthy,” said Letterman. It says Letterman is worth around $400 million; wow that rich! BUT, President Trump is worth (estimates vary) between 3 and 9 BILLION…. I don’t see how that’s ‘pretending’…. sounds like Letterman is suffering from TDS, jealousy, stupidity, old age, and ignorance! I’m glad I never watched his lousy show… I preferred Jay Leno.

  6. abolishliberalism

    June 13, 2019 at 9:39 am

    Well Dave? Can you really Blame POTUS Trump for acting this way? Running a country, especially one like the USA, and in this particular time in history isnt an easy task. Not only did he come into the job with so much he had to fix BEFOR he could actually begin working on the core problems that Obama didnt even look at, he had to fight like hell just to get elected because the Onslaught of mud that was throw at him from the left was probably 10 times that of which ANY Presidential campaign had to withstand. And then as soon as he takes office he is investigated for a sham charge of Colluding with Russia to win the election AND he is then Stonewalled by the left when he tries to do anything, even fill his cabinet!! POTUS Trump has had to claw and fight and force his way through the muck of the DC swamp just to BEGIN working and after a constant, never ending two year battle against the whole of the left, Hollywood and the entertainment industry, AND the left wing owned Liberal media… He has STILL dont more for the American people than Obama did in what turned out to be just an “8 year long, apology and Make-friends-with-everyone-even-the terrorists-Tour”!!! So yeah, Of course he has changes and isnt the Jovial, Younger, Happier New York City real-estate Builder / Mogul he was when he was in his 30s and 40s, much the same you YOU aren’t the Funny, down-to-earth, Happy, Talented, Talk show host you used to be! Now you’re just a bitter, old, rude, Red Neck wanna be with a huge chip on your shoulder who seems angry at the world!

  7. Lawrence Rataczak

    June 13, 2019 at 12:16 pm

    People whom we have made rich spew shit out of their mouths and get half the nation maybe more people to hate them are they really that stupid or that naive. Businesses are closing at a record pace and people still lose half their business just by being ignorant

  8. Ken M

    June 13, 2019 at 4:03 pm

    Hollywood Hypocrite and loser, he was never funny.

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