Leaked recordings of the two men's conversations between 1993 and 2015 reveal some of the the President’s more uncensored thoughts about women. In the interviews, Mr Trump and Mr Stern frequently rate women’s appearances and dish about their various sexual escapades.
In one interview, which was anonymously leaked to the website Factbase this month, Mr Stern asks if it’s true that Mr Trump has “banged some of the greatest beauties on the planet.”
“True. Some of the greats in history,” Mr Trump responds.
Later, when asked if he requires STD tests from all of the “greats” he bangs, Mr Trump responds: “I own 25 percent of Goodyear Tire and Rubber" – a reference to using a condom.
In another interview, Mr Stern asks the billionaire about his third wife, Melania.
“Have you ever felt her up in public?” Mr Stern asks.
“Yeah,” Mr Trump replies, before clarifying: “I'm very well behaved, actually, and almost always I'm very down the middle.”
Several times, the two men compare Melania Trump to Mr Trump’s first wife, Ivana. In one interview, Mr Trump says his first wife’s Czech accent was “terrible” and that he “couldn’t stand it”.
Mr Stern refused to release old recordings during the presidential campaign, claiming it would be a “betrayal”.
“I feel Donald Trump did the show in an effort to be entertaining and have fun with us, and I feel like it would be a betrayal to any of our guests if I sat there and played them now where people are attacking him,” Mr Stern said in 2015.
Mr Trump, meanwhile, has claimed that people “love” the interviews he did with the so-called shock jock.
“I never anticipated running for office or being a politician, so I could have fun with Howard on the radio and everyone would love it. People do love it,” the then-candidate said last year.
During his campaign, however, it appears Mr Trump attempted to tone down his comments. In a 2015 interview, the candidate declined Mr Stern’s invitation to rate journalist Megyn Kelly’s attractiveness.
“Well, you know, in the old days I would not have minded answering that question, but today I'll take a pass,” he said.
Some of Mr Trump’s other, more vulgar comments have come back to haunt him, however. A leaked recording of the businessman bragging about grabbing women “by the p****” sparked outcry during the campaign, and caused many Republicans to call on him to step down.
Mr Trump later apologised for the remarks.