Howard Stern Said Trump Rated Ivanka’s Looks (& She Was Hotter Than Angelina Jolie)

The next episode of My Next Guest Needs No Introduction on Netflix will feature the shock jock Howard Stern. The streaming video service hasn't posted the full episode yet, but one of the topics that host David Letterman will explore was previewed in a YouTube video uploaded Monday. In the clip, Stern talked about interviewing Donald Trump. He called the president a good radio guest and revisited how Trump used to speak about his daughter — and always rating her a 10.

"I'd say, 'Donald.' Actually, I'd call him 'Mr. Trump.' I'd say, 'Mr. Trump, umm, tell me, who are the great beauties? If I ask you some names, can you tell me who the great beauties are?'" Stern recalled, going on to share the president's answer.

Stern told Letterman about Trump's response. "He goes, 'First of all' — straight face — 'the great beauties, Howard, are not actresses. It’s models. A lot of these girls who... anyone who works in the entertainment industry, I’ve only seen 6s and 7s," Stern said.

"So I’d be like, well Donald, I think Angelina Jolie is a great beauty," Stern continued. "‘7!’ He’d go, ‘You know who’s a great beauty?’ I’d go, ‘Who?’ ‘My daughter, Ivanka! Now she’s a 10.’ So we’d have these discussions.” Letterman cringed in response.

To Stern, that made Trump a good guest. “To me, a guest who comes on and says anything that is in his mind is a great guest,” Stern told Letterman. “He would get on, and no matter what I asked him, he would answer in a very sincere and thought-out way.”

Many of these conversations have now become infamous, which Stern acknowledged. "Of course, with the Internet now all these tapes are out there," he told Letterman. An entire catalog of the interviews is available here.

Trump was a guest on Letterman's past show, too, before he became a serious candidate for president. In fact, Trump's first tweet ever was about an upcoming appearance on The Late Show. His appearances there were significant enough to be explored by The New York Times years later.

His interviews of the then business and real estate mogul — more than 30 — were a mixed bag. In one instance, Letterman confronted Trump about his attacks on China, asking him where Trump clothing was produced. He then grabbed a tie from behind the desk and showed it was made in China.

But other moments showed Letterman also being deferential, apologizing to Trump for calling him a racist over the birther attacks on President Obama.

But none of those appearances were as controversial as the Stern interviews were.

In an April 2010 interview, Stern asked Trump about Ivanka marrying Jared Kushner. He once again mentioned her looks. "She is a great girl. She's a beautiful girl. She — every guy wanted to get Ivanka," Trump told Stern.

Stern, though, spoke disrespectfully about Ivanka, egging on Trump. In October 2007, Stern said:

If I wasn't in love with Beth, I would totally be dating Donald's daughter. She is getting hotter and hotter, getting hotter, and hotter she's wearing hotter outfits and she really is good in business. I mean, to me that's a hot package and it would drive Donald nuts.

Trump did say it would drive him nuts. Later that same episode, Trump once again mentioned Ivanka's looks. "No I tell you, Ivanka has — she's really become a great beauty, but she's also really smart and she's doing very well," Trump told Stern.

There's plenty to unpack both from Stern and Trump's interviews, but also Letterman and Trumps. For more insights, check out My Next Guest Needs No Introduction when this episode drops on May 31.