David Letterman was the king of 'Late-Night'. However, despite his status, he wasn't short on awkward interviews. At times, those would be self-inflicted, especially during convos alongside certain celebs he didn't want to interview, like Marilyn Manson. Another person he never looked like he wanted to interview was none other than Donald Trump.

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Despite their different views, Trump was a regular on the show, appearing several times. We'll take a look at their final conversation, along with David's current opinion on Trump, which has changed drastically these days.

What Happened Between Donald Trump And David Letterman During Their Final Encounter On 'The Late Show'?

Back in the day, Donald Trump was a frequent guest on David Letterman's 'Late-Show'. By the looks of it, they got along fine, though Dave would throw a few jabs every now and then.

It seems like Letterman's stance on Trump changed in the recent years however, as he discussed alongside The Hollywood Reporter, "I think he just liked being on TV. I had no sense that he was the soulless b****** that he’s turned into.”

Letterman would also rip on Trump's status in the past, “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. Is that putting too fine a point on it?” He added, “I don’t even care if it’s recorded, I would just like to talk to the guy, because, as I said before, he knows me, I know him — what the hell went wrong?!”

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For Dave, his opinion soured when Trump was President, stating that he was not a fan of being represented as an American by Trump.

  • According to David Letterman, he interviewed Donald Trump more than 30 times.

Despite his harsh words today, things appeared to be much more low-key between the two during his many appearances on the show. Though in truth, Letterman was never afraid to take a jab at Trump, especially during their final interview.

David Letterman Had To Land A Joke Before The Interview Finished

The final interview between Trump and Letterman took place on the 'Late-Show' during January 2015. During the interview, Trump stated that he was eager to return one last time.

Everything was normal during their conversation, though Letterman did tease Trump about a possible Presidency run. At that point, Trump still wasn't confirming or denying the rumors.

Just as the interview was coming to an end, Letterman decided to take one final shot at 'The Apprentice' host, talking about his failed real estate in Atlantic City. This would be followed up by Trump's closing words, stating "has your barber ever made a bad decisions?" He would then state, "that's all I got Don," only for Trump to laugh it off.

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Since then, Letterman has spoken about the interviews, revealing that he would enjoy "smacking Donald around," during their interviews. "I think he just liked being on TV, and he was an excellent guest for somebody I could just beat up on and smack around and stuff," Letterman said. "He's just like a goofball ... a bonehead."

The final interview between the two has almost one million views. In terms of the comments, most fans are surprised as to how different the reaction for Trump was back then.

Fans Were Surprised By The Interview Looking Back

In the comments' section of the video, fans were surprised by a couple of things from the interview. For one, fans were discussing how different the reactions were for Donald. In addition, they would also talk about how Trump is the same exact person on the show compared to his early days alongside Dave in the '80s.

  • Donald Trump was also a regular on the Howard Stern Show, appearing at least a dozen times.

"It's amazing how a little more than two years ago they loved him."

"He's literally the exact same guy from when he was on this show in the 80s."

"Looked at his Letterman interview of 1986-87. In 30 years his views on the US hasn't changed. Only now he is in a position to do something about it."

"Little did everybody know when they first watched this what would then happen. LOL."

We can only image what a conversation would be like with these two, in this day and age.

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