In a conversation just months after her death. Stern started to imagine a conversation between Trump and Diana, saying: "Hey Lady Di, would you go to the doctor?" Stern mockingly asks.
Trump then runs with the joke, imagining the conversation with the royal. "Go back over to my Lexus, because I have a new doctor," he says, as if addressing her. "We wanna give you a little checkup."
The pair were carrying on an earlier joke in the conversation where Trump said he always made sure women had HIV tests before sleeping with him.
DIANA WAS HIS ONLY REGRET
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The now US president, Trump also commented on Diana's appearance in the interview.
"She had times when she didn't look great, and sometimes you look better than anybody in the world. But she was a supermodel.
"She was crazy, but you know these are minor details," Trump added.
Later that year in November 1997, Trump published his book, The Art of the Comeback, in which he wrote: "I only have one regret in the women department - that I never had the opportunity to court Lady Diana Spencer."
"I met her on a number of occasions," Trump stated. "I couldn't help but notice how she moved people. She lit up the room with her charm, her presence. She was a genuine princess - a dream lady."
A few years later he spoke about Princess Diana once again: "She had the height, she had the beauty, she had the skin, the whole thing," he said during the May 2000 call-in. "She's magnificent."
Trump called in to the show to discuss his top ten hottest women list with Stern in the recording, released by Factbase.
Princess Diana was third on his list, after ex-wife Ivana in second and now-First Lady Melania in first.
The show saw him also make outlandish comments about Angelina Jolie, who he said had lips that were too big, as well as Mariah Carey and Cindy Crawford, who he also said he would sleep with.
TRUMP GAVE DI "THE CREEPS"
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The pair met on a number of occasions, including at a charity dinner for some of New York's most powerful at the Hilton Hotel in Manhattan in 1995, where fate had placed Donald Trump on the princess's table - although his second wife Marla was also present.
He didn't make a move at the dinner, but six months later - soon after Diana announced her divorce from Prince Charles in July 1996 - she was surprised to receive a huge basket of flowers from Trump for her 35th birthday.
Trump attached a message expressing his sympathy over her divorce, his regard for her and even, it is said, suggesting they get together.
However, it's clear the princess didn't feel the same way.
British broadcaster Selina Scott claimed he actually gave Diana "the creeps".
She says the billionaire businessman pursued the Princess of Wales to the point of "stalking" in the mistaken belief he "had a shot" with her.
Writing in the Sunday Times, she said: "He bombarded Diana at Kensington Palace with massive bouquets, each worth hundreds of pounds.
"Trump clearly saw Diana as the ultimate trophy wife. As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do. It had begun to feel as if Trump was stalking her.
"When she died in the tragic accident in Paris in 1997 Trump told friends his biggest regret was that they hadn't dated. He said that he always thought he had a chance of romance and would have had a 'shot' with her."
Trump's spokesman said at the time that they liked each other a lot but nothing ever came of it.
