Among the topics Trump discussed - his daughter Ivanka's physique and checking out of a relationship with women after they turn 35.
When Stern asked in 2006 about whether his daughter had breast implants, Trump said of the then-24-year-old Ivanka that "she's actually always been very voluptuous.She's tall, she's nearly 6 feet tall and she's been, she's an incredible beauty".
"The first time I saw her she walked into the room, I said, 'Who the hell is that?' " he said.
The newly unearthed Stern interview is not the only time Trump has objectified his daughter.
"I wouldn't say 300, I would say could be about 375", said Trump.
Howard Stern: You mean that? The most recent headline comes from a 2006 Howard Stern interview in which Stern is questioning the real estate mogul about the authenticity of his daughter's breasts. In another, Trump responds to a question from Stern about whether he'd stay with Melania if she was disfigured in a vehicle accident by asking, "How do the breasts look?" "She is tall, she's nearly 6 feet tall and she's been, she's an unbelievable beauty". And then Stern basically baits Trump into giving him the OK to call his daughter "a piece of ass".
In yet another tape in 2006, Trump was asked by Stern if he could now be "banging" 24 year-old women.
"Yeah, she's really something, and what a beauty, that one". At the time, Trump was 55, which is 34 years older than his 21 year-old date, nearly old enough to be her grandfather!
Ivanka, who has been her father's most vocal supporter throughout his campaign, has remained surprisingly silent in the days since the release of the audio.
Trump has apologized over the content of the video and vowed to stay in the race, pushing back against a growing number of Republican leaders who have announced they won't vote for him. "I'll admit it", Mr Trump is heard saying. "I get older, they stay the same age". "I better use some Tic Tacs just in case I start kissing her", Donald added, when he noticed soap star Arianne Zuckerfrom afar.
In one clip from 2002, Trump discusses feeling embarrassed being seen on dates with younger women, saying, "Over the past couple of years, I'd go out with somebody and she's like 21, and she's talking about you know, 'What are you doing?' and she's studying algebra".
When Stern asks Trump if he's "had a black woman in bed", Trump responds: "Well, it depends on what your definition of black is". Yeah, it's fine, his own daughter is totally a piece of ass.