Radio host Howard Stern has recalled his creepiest interview with Donald Trump before the businessman became president.

In a clip from the next instalment of David Letterman's Netflix series, My Next Guest Needs No Introduction, the DJ recounts the former reality star's unsettling way of rating the appearance of daughter Ivanka.

In the episode debuting on the streaming service on May 31, Stern said Mr Trump used to give his offspring as an example of a woman who was "a ten", ranking her above Angelina Jolie among the "great beauties" of the world.

"To me, a guest who comes on and says anything that is on his mind is a great guest," Stern says in the Letterman clip. "No matter what I asked him, he would answer in a very sincere and thought-out way."

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On one occasion, Stern says, he asked Mr Trump for his personal list of the "great beauties" in the world.

With a straight face, the businessman replies: "First of all, the great beauties are not actresses. … Anyone who works in the entertainment industry, really, I've only seen sixes and sevens."

Stern suggests Jolie should be at the top of such a list, but Mr Trump dismisses the idea, giving her a seven.

"Really, why?" asks Stern.

"You know who's a great beauty?" replies Mr Trump. "My daughter, Ivanka. Now she's a 10!"

Letterman has interviewed celebrities including George Clooney, Jay-Z, Tina Fey and Barack Obama in his series, which launched in January.

Mr Trump has been a regular guest on radio veteran Stern's shows, famously appearing with then-girlfriend Melania in 1999 and discussing their sex life.

In the interview with Melania, shock jock Stern repeatedly asks if she is naked.

"Almost," she replies.

"Ahhh, I've got my pants off already," he groans.

He then asks Melania how often she and her then-boyfriend have sex.

"We have a great, great time," she responds, saying the pair were intimate "even more" than daily.

Stern even begs Mr Trump to have sex with Melania on air to increase his ratings, while Mr Trump laughs and appears to encourage the line of questioning.

"Oh man, she's naked there, isn't she?" Stern asks Mr Trump.

"She is actually naked," he replies. "It's a thing of beauty."