In a candid and revealing interview with David Letterman on My Next Guest Needs No Introduction , Howard Stern shared some peculiar insights, including Donald Trump ’s unique beauty rankings. The conversation touched on various topics, underscoring Stern’s storytelling prowess and his experiences with the President-elect. Stern, famous for his straightforward approach during interviews, shared that Trump was a candid and engaging guest on his radio show. According to Stern, Trump would answer any question: “No matter what I asked him, he would answer. In a very sincere and thought-out way.”
When Stern asked Trump about true beauties in the world, the former President dismissed various actresses, calling them ‘6s and 7s.’ Stern, challenging Trump’s perspective, mentioned Angelina Jolie , to which Trump responded with a modest ‘7.’ The now-convicted President added, “You know who’s a great beauty? My daughter Ivanka. Now, she’s a 10,” as per Variety .
I watched David Letterman talk to Howard Stern and Jerry Seinfeld. Donald Trump came up both times. The general consensus is he was a great interviewee, but the level of swerve when it comes to how he speaks about his daughter… I’m just saying.
— Gooner Rue (@GrymDaGooner) November 24, 2020
Meanwhile, in September 2023, Stern also addressed people who labeled him ‘woke’ for his views on Trump. “I’ll tell you how I feel about it. To me, the opposite of woke is being asleep. And if woke means I can’t get behind Trump, which is what I think it means, or that I support people who want to be transgender or I’m for the vaccine, dude call me woke as you f—— want,” he exclaimed. “I said to [co-host] Robin [Quivers], and I hate to say this, but, but I said to her, ‘I’m actually gonna probably have to run for president now. The problem with most presidents is they have too big of an agenda. The only agenda I would have is to make the country fair again.”
David @letterman looks back on his interviews with Donald Trump, including where he questions his net worth. “There, he seemed like a guy … were I ever to get the chance to talk to him,” Letterman says. “I would say, ‘When did you become such a goon?’” https://t.co/tnUlRGUyAt pic.twitter.com/wiw5mkVKHA
— The View (@TheView) May 31, 2019
Letterman, another seasoned host who had Trump on his show numerous times, shared a different perspective. Referring to Trump as ‘psychotic,’ Letterman said, “Everybody says, ‘Oh, wouldn’t you like to talk to Donald Trump [today]?’ And I would. I would just like to say, ‘Don, it’s Dave. Remember me? I want to talk to the real Donald Trump.’ 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— behaves like that?!”
As per The Washington Post , he further added, “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? 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?!” As both hosts reflected on their experiences with Trump, it highlighted the multifaceted nature of the President’s public image.
This article originally appeared 10 months ago.